The present invention relates to histone deacetylase inhibitor compounds characterised by the presence of a hydroxamic group, to preparations for obtaining them and to their use for preparing pharmaceutical formulations to be employed for treating pathologies in which the mechanism of gene regulation plays an essential role.
In particular the present invention concerns a compound having a general formula (I):
in which v=0, 1, 2
in which n=0, 1, 2
in which R5 is a H or a C1-3 alkyl
in which:
To be considered excluded from the present invention are products in which:
B is chosen from —NR5-CO— or —NR5-SO— and at the same time
L2 is chosen from —(CH2)p-CO— or —(CH2)p-CH═CH—CO—. The relative prodrugs of general formula (III) and (IV) also form part of the present invention
In which Rx can be Ac, COEt, CO-nPr, CO-iPr, CO-tBu, benzoyl, pNO2benzoyl, CH3, Et, nPr, iPr, tBu, Benzyl, tetrahydropyranyl.
Ry and Rz independently indicate a H or a C1-3 alkyl group.
Also forming part of the present invention are all possible optical isomers, such as enantiomers and/or diastereoisomers, derived from the possible presence of chiral centres in the compounds of general formula (I), and possible mixtures thereof either as racemes or in various ratios thereof, and their inorganic and organic acid salts.
Histone deacetylase is known to have an essential role in the mechanism that regulates gene expression. Inhibitors of histone deacetylase (HDAC) induce hyperacetylation of histones, with consequent alteration of gene expression itself. It follows that said inhibitors are useful as therapeutic or prophylactic agents for pathological states caused by abnormal gene expression, such as inflammatory disorders, diabetes, complications of diabetes, homozygotic thalassaemia, fibrosis, cirrhosis, acute promyelocytic leukaemia (APL), transplant rejection, auto-immune diseases, protozoan infections, tumors and the like.
The enzyme histone deacetylase is already well known and, via X-ray and SAR studies of various inhibitor classes, the structural characteristics that a potential inhibitor should possess have been elucidated; in particular a) a domain able to bind a metal (specifically Zn), b) a linker able to occupy a channel of the enzyme, c) a surface recognition domain that interacts with the structures on the rim of the enzyme active site (J. Med. Chem., 2003, 46(24), 5097-5116).
In the last few years many examples of HDAC inhibitors with the aforesaid structural characteristics have become apparent.
For example, compounds that present a n-hydroxyamide and a linear linker are described in: Bioorganic & Medicinal Chem Letters (2002), 12, 2919-2923; J Med Chem (2002) 45 (13), 2877-2885; J Med Chem (2002), 45 (4), 753-757; Bioorganic & Medicinal Chem Letters (2004), 14, 449-453. Other publications demonstrate hydroxamic acids in which the linker is not linear; in Bioorganic & Medicinal Chem Letters (2001), 11, 2847-2890 the linker is represented by phenyl-ethyl or styryl; in Bioorganic & Medicinal Chem Letters (2002), 12, 1347-1349 the linker is a phenyl or a cyclohexyl; the compounds described in WO2004013130 present a linker consisting of athiophene.
Other authors have shown the possibility of substituting hydroxamic acid with other groups able to bind the metal of the enzyme active site, for example with amides (J. Med Chem (2003), 46, 820-830; or in EP847992) or electrophile ketones. WO2004069133 describes compounds in which, based on the aforementioned scheme, the metal binding group is represented by a phenylenediamine amide, and the linker by a heterocycle chosen from indole, benzothiophene or benzofuran. WO2005040101 also claims hydroxamates containing carbamoyl piperidino groups or the like as general meanings.
Notwithstanding all that is already known on the subject, there is still however a great need to identify new HDAC inhibitors which allow us to prepare new drugs for the treatment of the many pathologies that are potentially curable via this mechanism of action.
The aim of the present invention is to provide new HDAC inhibitors of general formula (I), useful as drugs, and the pharmaceutical compositions that contain them, as active ingredients for the treatment or prophylaxis of pathologies such as inflammatory disorders, diabetes, complications of diabetes, homozygotic thalassaemia, fibrosis, cirrhosis, acute promyelocytic leukaemia (APL), transplant rejection, auto-immune diseases, protozoan infections, tumors and the like.
The present invention provides compounds of general formula (I) as heretofore described.
A group of preferred compounds of the present invention are those of general formula (II)
in which v=1
in which n=0, 1, 2
in which R5 is a H or a C1-3 alkyl
in which:
To be considered excluded from the present invention are products in which:
B is chosen from —NR5-CO— or —NR5-SO2— and at the same time
L2 is chosen from —(CH2)p-CO— or —(CH2)p-CH═CH—CO—.
The relative prodrugs of general formula (III) and (IV) also form part of the present invention
in which Rx can be Ac, COEt, CO-nPr, CO-iPr, CO-tBu, Benzoyl, pNO2-Benzoyl, CH3, Et, nPr, iPr, tBu, Benzyl, tetrahydropyranyl
Ry and Rz independently indicate a H or C1-3 alkyl group.
Also forming part of the present invention are all possible optical isomers, such as enantiomers and/or diastereoisomers, derived from the possible presence of chiral centres in the compounds of general formula (I), and possible mixtures thereof either as racemes or in various ratios thereof, and their inorganic and organic acid salts.
A group of particularly preferred compounds of the present invention are those of general formula (II) in which v=1
in which n=0, 1
in which R5 is a H or a C1-3 alkyl,
in which:
Furthermore, possibly preferred salts are intended as salts obtained with inorganic or organic acids chosen from: hydrochloric, hydrobromic, phosphoric, sulphuric, nitric, acetic, trifluoroacetic, methanesulfonic, toluenesulfonic, oxalic, succinic, malonic, adipic, benzoic acids.
The HDAC inhibitors of the present invention can be synthesised according to reactions known in the state of the art, but which can vary greatly on the basis of the series of synthesis steps needed to prepare the individual compounds summarized in general formula (I).
Some descriptive schemes by way of non-limiting examples are given below. From said schemes the synthesis of all the compounds represented in general formula (I) can be easily deduced or extrapolated by experts of the art:
In some cases the formation of amide bonds also allows passage along the solid phase synthesis paths developed in peptide chemistry based on the use of resin. Some representative examples of the present invention and the method for their synthesis are given below.
DIPEA (0.11 ml, 0.66 mmols) and phenylacetyl chloride (0.043 ml, 0.33 mmols) are added to a suspension of 4-piperidino butyric acid methyl ester hydrochloride (100 mg, 0.33 mmols) in anhydrous CH2Cl2 (10 ml), maintained at 0° C. under N2. The resulting mixture is left under agitation for 2 hours at ambient temperature.
At the end of the reaction (HPLC monitoring) the mixture is diluted with CH2Cl2 and 15 ml of 5% NaHCO3 are added. The two phases are separated and the organic phase is then further washed with 5% NaHCO3 (3 times) and ssNaCl. The organic phase is dried over Na2SO4 and the solvent evaporated under reduced pressure to obtain the desired amide with quantitative yield.
Synthesis of the hydroxaminic acids 3, 5, 7, 9, 11 starting from the corresponding esters (method A) or carboxylic acids (method B).
A solution of KOH (210 mg, 3.74 mmols) in MeOH (2 mL) is added to a solution of hydroxylamine hydrochloride (190 mg, 2.72 mmols) in MeOH (2 mL) maintaining the temperature at 0° C. The solution is then stirred for 15 minutes while at 0° C. A solution of the methyl ester (0.34 mmols) in MeOH/THF (4 mL) is added and the resulting mixture maintained at ambient temperature for 12 hours under agitation. At the end of the reaction (HPLC monitoring) the pH is adjusted to about 8 by adding a 6N HCl solution.
At this point extraction in the organic phase can be undertaken if the product is not too water-soluble, or, otherwise, purification by inverse phase chromatography.
DIPEA (0.085 ml, 0.48 mmols) and BSA (0.234 ml, 0.96 mmols) are added to a solution of 4-piperidine butyric acid hydrochloride (100 ml, 0.48 mmols) in anhydrous CH2Cl2 (10 ml). The mixture is allowed to react at ambient temperature for 2 hours, then phenylacetyl chloride (0.063 ml, 0.48 mmols) is added. The resulting mixture is stirred at ambient temperature for 12 hours.
At the end of the reaction (HPLC monitoring) 15 ml of 5% NaHCO3 are added and the mixture is left under vigorous agitation for 30 minutes. The two phases are separated and the aqueous phase is acidifed to pH 2.
The aqueous phase is extracted with EtOAc, the organic extracts are washed with ssNaCl, dried over Na2SO4 and the solvent evaporated under reduced pressure to obtain the desired carboxylic acid (130 mg, 95%) with suitable purity.
COCl2 (0.045 ml, 0.54 mmols) and a catalytic quantity of DMF are added to a solution of the acid (130 mg, 0.45 mmols) in 5 ml of anhydrous CH2Cl2. After two hours the CH2Cl2 is evaporated under reduced pressure, twice redissolving and re-evaporating the crude reaction product again using CH2Cl2. To the acyl chloride thus formed, dissolved in 5 ml of anhydrous CH2Cl2, are slowly added 5 ml of an aqueous solution of NH2OH HCl (32 mg, 0.45 mmols) and NaHCO (75 mg, 0.9 mmols). The mixture is allowed to react for 1 hour under vigorous agitation at ambient temperature.
At the end of the reaction (HPLC monitoring) the two phases are separated, the organic phase is washed with ssNaCl, dried over Na2SO4 and concentrated under reduced pressure. The crude product obtained is purified by phase inverse chromatography, to obtain 82 mg of the desired product (60%).
Phenylacetic aldehyde (0.046 mL, 0.40 mmols) and sodium triacetoxyborohydride (190 mg, 0.90 mmols) are added sequentially to a solution of 4-piperidin-4-yl-butyric acid methyl ester hydrochloride salt (80 mg, 0.36 mmols) in THF (3 mL). The resulting mixture is stirred at ambient temperature for four hours. 10% NaHCO (10 mL) and EtOAc (10 mL) are then added and the two phases separated. The organic phase is washed with water, ssNaCl and dried over Na2SO4. Filtration and removal of solvents by reduced pressure provide the desired product with a quantitative yield, which can be used as such in the following reaction.
A solution of 4-piperidin-4-yl-butyric acid methyl ester hydrochloride salt (98 mg, 0.443 mmols), DIPEA (0.091 mL, 0.532 mmols) and benzylisocyanate (0.051 mL, 0.499 mmols) in dichloromethane (4 mL) is stirred at ambient temperature for 3 hours.
At the end of the reaction (HPLC monitoring) a portion of aminomethyl polystyrene resin (50 mg, 1 mmol/g loading) is added to remove excess isocyanate and the resulting mixture is stirred for a further 2 hours. The solution is filtered and concentrated under reduced pressure to obtain the desired product (140 mg, 99%) which can be used as such in the following reaction.
A portion of benzenesulfonyl chloride (45 mg, 0.26 mmols) and one of DIPEA (70 mg, 0.54 momls) are added to a solution of 4-piperidin-4-yl-butyric acid methyl ester hydrochloride salt (60 mg, 0.27 mmols) in anhydrous CH2Cl2 (2 mL).
At the end of the reaction (HPLC monitoring) the mixture is diluted with CH2Cl2 and washed with 5% NaHSO4, 5% NaHCO3 and ssNaCl; the organic phase is dried over NaSO4 and evaporated. The crude product thus obtained is purified by chromatography (silica, petroleum ether/AcOt 8:2). 75 mg (90%) of the desired product are obtained with suitable purity.
200 mg of the commercial resin N-Fmoc-hydroxylamine-2-chlorotrityl polystyrene (conc. 0.5 mmols/g) is allowed to pre-swell for 1 hour in 2 ml of dichloromethane (DCM). The resin is filtered off and suspended in 2 ml of a solution of 20% piperidine in dichloromethane. After 30 minutes the resin is filtered off and resuspended in 2 ml of a solution containing 20% piperidine in DMF. After 30 minutes the resin is filtered off and washed with DCM (4×2 ml). At the end the resin is re-swollen in DCM for 20 minutes.
A solution of HOAt (68 mg, 0.50 mmols) in 1.5 ml of anhydrous DMF is added to a solution of 4-[N-(fluoren-9-ylmethoxycarbonyl)piperidin-4-yl]-butanoic acid (200 mg, 0.50 mmols) in 1.5 ml of DCM. 0.08 ml of diisopropylcarbodiimide (63 mg, 0.50 mmols) are slowly added and the mixture is maintained for 1 hour under agitation at ambient temperature. The solution is poured onto polystyrene resin and the suspension stirred for 18 hours at ambient temperature. The resin is filtered off and suspended in 2 ml of a solution of 20% piperidine in dichloromethane. After 30 minutes the resin is filtered off and washed sequentially with DMF (2×2 ml) and DCM (2×2 ml). At the end the resin is re-swollen in DCM for 20 minutes.
The qualitative ninhydrin assay on completion of the acylation reaction (Kaiser et al Anal. Biochem. 1970, 34, 595) proves to be negative.
A solution of HOAt (68 mg, 0.05 mmols) in 1.5 ml anhydrous DMF is added to a solution of Fmoc-D-Phe-OH (194 mg, 0.50 mmols) in 1.5 ml of DCM. Diisopropylcarbodiimide (0.08 ml, 63 mg, 0.50 mmols) is slowly added and the mixture maintained for 1 hour at ambient temperature under agitation. The solution is poured onto the polystyrene resin and the suspension agitated for 18 hours at ambient temperature. The resin is filtered off and suspended in 2 ml of a solution of 20% piperidine in dichloromethane. After 30 minutes the resin is filtered off and washed sequentially with DMF (2×2 ml) and DCM (2×2 ml). 100 μl of trifluoroacetic acid and 100 μl of triethylsilane are added to the thus obtained resin, re-swollen in 2 ml DCM for 20 minutes. It is maintained under agitation for 15 minutes at ambient temperature. The resin is filtered off and washed twice with DCM and MeOH alternately. The filtrates are pooled and evaporated to dryness. Grinding the crude product thus obtained with ethyl ether provides the desired product (35 mg, 80% yield) with a purity of 95%. MF:C18H27N3O3, MW: 333.43.
0.048 ml (51 mg, 0.50 mmols) of Ac2O and 0.085 ml of DIPEA (65 mg, 0.50 mmols) in DCM are added to the resin obtained in step F, re-swollen in 2 ml of DCM for 20 minutes. The resin is agitated for 18 hours at ambient temperature then filtered off and washed sequentially with DMF (2×2 ml) and DCM (2×2 ml). 100 μl of trifluoroacetic acid and 100 μl of triethylsilane are added to the thus obtained resin, re-swollen in 2 ml DCM for 20 minutes. It is maintained under agitation for 15 minutes at ambient temperature. The resin is filtered off and washed twice with DCM and MeOH alternately. The filtrates are pooled and evaporated to dryness. Grinding the crude product thus obtained with ethyl ether provides the desired product (28 mg, 75% yield) with a purity of 95%. MF: C20H29N3O4, MW: 375.47.
A mixture of HOAt (20 mg, 0.15 mmols), Fmoc-D-Ser-OH (49 mg, 0.15 mmols) and diisopropylcarbodiimide (0.024 ml, 18 mg, 0.15 mmols) in 3 ml of DMF/DCM, previously maintained at ambient temperature for an hour, is added to the resin obtained in Step C, re-swollen in 2 ml of DCM for 20 minutes. The suspension is agitated for 18 hours at ambient temperature then the resin is filtered off and washed sequentially with DMF (2×2 ml) and DCM (2×2 ml).
The resin is filtered off and suspended in 2 ml of a solution of 20% piperidine in dichloromethane. After 30 minutes the resin is filtered off and washed sequentially with DMF (2×2 ml) and DCM (2×2 ml).
To the resin obtained in Step E and re-swollen in 2 ml of DCM for 20 minutes are added the mixture of HOAt (68 mg, 0.5 mmols), benzo[b]thiophene-2-carboxylic acid (90 mg, 0.5 mmols) and 0.08 ml of diisopropylcarbodiimide (63 mg, 0.5 mmols) in 3 ml of DMF/DCM previously held at ambient temperature for 1 hour. The suspension is agitated for 18 hours at ambient temperature. The resin is filtered off and washed sequentially with DMF (2×2 ml) and DCM (2×2 ml).
100 μl of trifluoroacetic acid and 100 μl of triethylsilane are added to the thus obtained resin, re-swollen in 2 ml DCM for 20 minutes. It is maintained under agitation for 15 minutes at ambient temperature. The resin is filtered off and washed twice with DCM and MeOH alternately. The filtrates are pooled and evaporated to dryness. Grinding the crude product thus obtained with ethyl ether provides the desired product (41 mg, 75% yield) with a purity of 95% (HPLC, 214 nm). MF: C30H31N3O6S2, MW: 593.73.
The relative prodrugs of general formula (IV) and (V) also form part of the present invention, for whose production the preparation of suitable syntones in which the hydroxamic acid function is protected in the hydrolysable group of the ‘prodrug’ is generally preferred.
These syntones are then used for synthesis of the required compounds by synthetic paths totally similar to those used for compounds not defined as ‘prodrugs’.
Non-limitative examples of synthesis of syntones for prodrugs are:
Pyridine (0.019 ml, 0.23 mmols, 1.5 eq.) and acetic anhydride (0.022 ml, 0.23 mmols, 1.5 eq.) are added to a solution of 4-(3-hydroxycarbamoyl-propyl)-piperidine-1-carboxylic acid benzylamide (50 mg, 0.16 mmols, 1.0 eq.) in anhydrous DCM (3 ml) and the resulting mixture allowed to react at ambient temperature for 12 hours. At the end of the reaction, after diluting with DCM and washing with 1 N HCl (5 ml), the phases are separated. The organic phase is washed washing with ssNaCl, dried over Na2SO4 and concentrated under reduced pressure. The crude product obtained is purified by flash chromatography (30% petroleum ether in AcOEt then AcOEt) to obtain 45 mg of the desired monoacetylated product as a white solid (80%).
1H NMR (DMSO-d6, 400 MHz): δ (ppm) 0.90-1.03 (2H, m), 1.16-1.29 (2H, m), 1.32-1.48 (1H, m), 1.48-1.67 (4H, m), 2.11 (2H, t, J=6.8 Hz, CH2CO), 2.15 (3H, s, OCH3), 2.65 (2H, m, N(CHH)2), 3.98 (2H, m, N(CHH)2), 4.24 (2H, d, J=5.2 Hz, PhCH2), 6.97 (1H, m, NCONH), 7.16-7.36 (5H, m, ArH), 11.53 (1H, s, NHO)
MF: C19H27N3O4, MW: 361.43
Camphorsulfonic acid (37 mg, 0.16 mmols, 1.0 eq.) is added to a solution of 4-(3-hydroxycarbamoyl-propyl)-piperidine-1-carboxylic acid benzylamide (50 mg, 0.16 mmols, 1.0 eq.) and 2,2-diethoxypropane (0.076 mL, 0.47 mmols, 3.0 eq.) in anhydrous DCM (3 ml) and the resulting mixture is left under agitation at ambient temperature for 4 hours. At the end of the reaction a saturated aqueous solution of Na2CO3 (5 ml) is added and the phases separated. The aqueous phase is washed with Et2O (4×5 ml). The pooled organic phase is finally dried over Na2SO4 and concentrated under reduced pressure. The crude product is purified by flash chromatography (30% petroleum ether in AcOEt) to obtain 45 mg of the desired product (80%).
1H NMR (DMSO-d6, 400 MHz): 6 (ppm) 0.87-0.96 (2H, m), 1.17-1.30 (2H, m), 1.30-1.45 (1H, m), 1.46-1.68 (4H, m), 1.49 (6H, s, 2×CH3), 2.28 (2H, t, J=7.2 Hz, CH2CO), 2.63 (2H, m, N(CHH)2), 3.96 (2H, m, N(CHH)2), 4.22 (2H, d, J=5.2 Hz, PhCH2), 7.01 (1H, m, NCONH), 7.16-7.33 (5H, m, ArH)
MF: C20H29N3O3, MW: 359.46.
EDAC (69 mg, 0.36 mmols, 1.0 eq.) and HOBt (49 mg, 0.36 mmols, 1.0 eq) are added to a solution of 4-(1-benzylcarbamoyl-piperidin-4-yl)-butyric acid (100 mg, 0.328 mmols, 1.0 eq.) in anhydrous DMF (5 mL) and the mixture maintained under agitation at ambient temperature for 1 hour. O-(tetrahydro-2H-pyran-2-yl)hydroxylamine (13 mg, 0.33 mmols, 1.0 eq.) and DIPEA (0.042 mL, 0.49 mmols, 1.5 eq.) are then added and the resulting mixture left under agitation at ambient temperature for 12 hours.
At the end of the reaction (HPLC monitoring) a solution of 5% NaHCO3 (5 ml) and AcOEt (5 ml) are added and the phases separated. The organic phase is washed with ssNaCl, dried over Na2SO4 and concentrated under reduced pressure. The crude product obtained is purified by flash chromatography (AcOEt) to obtain 92 mg of the desired product (70%).
1H NMR (DMSO-d6, 400 MHz): δ (ppm) 0.93 (2H, dq, J=3.6 and 12.0 Hz), 1.11-1.22 (2H, m), 1.28-1.44 (1H, m), 1.44-1.74 (10H, m), 1.96 (2H, t, J=7.2 Hz, CH2CO), 2.62 (2H, m, N(CHH)2), 3.49 (1H, m, OCHH), 3.84-4.05 (3H, m, N(CHH)2 and OCHH), 4.21 (2H, d, J=5.6 Hz, PhCH2), 4.79 (1H, s, OCHO), 7.00 (1H, m, NCONH), 7.16-7.33 (5H, m, ArH), 10.91 (1H, s, NHO)
MF: C22H33N3O4, MW: 403.51.
Some non-limitative examples representative of the present invention implemented in accordance with the above described synthesis schemes and variations thereof are given below.
1H NMR (DMSO-d6, 400 MHz): δ (ppm) 0.93-1.25 (4H, m), 1.25-1.41 (1H, m), 1.47 (2H, m), 1.70 (2H, d, J=12.6 Hz), 1.91 (2H, t, J=7.2 Hz, CH2CO), 2.67 (2H, m, N(CHH)2), 3.70 (2H, d, J=12.6 Hz, N(CHH)2), 7.57 (1H, m, ArH), 7.65-7.75 (2H, m, ArH), 7.98 (1H, d, J=7.5 Hz, ArH), 8.65 (1H, s, OH), 10.32 (1H, s, NH).
MF: C15H21ClN2O4S, MW 360.85
1H NMR (DMSO-d6, 300 MHz): δ (ppm) 1.17-1.23 (5H, m), 1.38-1.46 (2H, m), 1.63-1.69 (2H m), 1.87 (2H, t, J=7.3 Hz, CH2CO), 2.43-2.48 (2H, m, (N(CHH)2), 2.76 (3H, s), 3.70 (2H, d, J=12.0 Hz, (N(CHH)2), 7.56 (1H, d, J=7.5 Hz, ArH), 7.71-7.75 (2H, m, ArH), 8.02 (1H, d, J=7.5 Hz, ArH), 8.18-8.21 (1H, m, ArH), 8.63 (1H, s OH), 8.68-8.71 (1H, m, ArH), 10.27 (1H, s, NH).
MF C20H26N2O4S, MW 390.49
1H NMR (DMSO-d6, 300 MHz): δ (ppm) 1.09-1.12 (2H, m), 1.14-1.24 (2H, m), 1.49-1.56 (3H m), 1.60-1.76 (2H, m), 1.94 (2H, t, J=7.3 Hz, CH2CO), 2.88-3.14 (2H, m, (N(CHH)2), 3.61-3.64 (1H, m, (N(CHH)2), 4.41-4.60 (1H, m, (N(CHH)2), 7.47-7.50 (1H, d, J=8.3 Hz, ArH), 7.56-7.61 (2H, m, ArH), 7.95-8.02 (4H, m, ArH), 8.66 (1H, s, OH), 10.34 (1H, s).
MF C20H24N2O3, MW 340.41
1H NMR (DMSO-d6, 300 MHz): δ (ppm) 0.75-1.24 (3H, m), 1.39-1.61 (4H, m), 1.76-1.87 (1H, m), 1.94 (2H, t, J=7.3 Hz, CH2CO), 2.80-3.00 (2H, m), 3.18-3.21 (1H, m, (N(CHH)2), 3.61-3.64 (1H, m, (N(CHH)2), 4.63-4.70 (1H, m, (N(CHH)2), 7.37-8.02 (7H, m, ArH), 8.66 (1H, s, OH), 10.34 (1H, s, NH).
MF C20H24N2O3, MW 340.41
1H NMR (DMSO-d6, 400 MHz): δ (ppm) 0.86-1.04 (2H, m), 1.11-1.20 (2H, m), 1.40-1.70 (5H, m), 1.94 (2H, t, J=7.5, Hz, CH2CO), 2.57 (1H, t, J=11.6 Hz, NCHH), 3.04 (1H, t, J=11.6 Hz, N(CHH),), 4.00 (1H, d, J=12.9 Hz, NCHH), 4.15 (2H, s, CH2Ar), 4.40 (1H, d, J=12.9 Hz, NCHH), 7.32-7.99 (7H, m, ArH), 8.66 (1H, s, OH), 10.33 (1H, s, NH).
MF: C21H26N2O3, MW: 354.44
1H NMR (DMSO-d6, 400 MHz): δ (ppm) 0.80-1.00 (2H, m), 1.11-1.20 (2H, m), 1.40-1.70 (5H, m), 1.91 (2H, t, J=7.1 Hz, CH2CO), 2.53 (1H, t, J=11.6 Hz, NCHH), 2.97 (1H, t, J=11.6 Hz, NCHH), 3.88 (2H, s, CH2Ar), 4.00 (1H, d, J=12.9 Hz, NCHH), 4.40 (1H, d, J=12.9 Hz, NCHH), 7.39 (1H, d, J=8.5 Hz, ArH), 7.44-7.55 (2H, m, ArH), 7.74 (1H, s), 7.83-7.93 (3H, m), 8.64 (1H, s, OH), 10.31 (1H, s, NH).
MF C21H26N2O3, MW 354.44
1H NMR (DMSO-d6, 400 MHz): δ (ppm) 0.95 (2H, dq, J=3.4 and 12.0 Hz), 1.12-1.23 (2H, m), 1.30-1.45 (1H, m), 1.51 (2H, m), 1.56-1.66 (2H, m), 1.94 (2H, t, J=7.0 Hz, CH2CO), 2.64 (2H, m, N(CHH)2), 3.93-4.03 (2H, m, N(CHH)2), 4.23 (2H, d, J=5.8 Hz, PhCH2), 6.99 (1H, t, J=7.0 Hz, NCONH), 7.17-7.34 (5H, m, ArH), 8.65 (1H, s, OH), 10.34 (1H, s, NH).
MF C17H25N3O3, MW 319.39
1H NMR (DMSO-d6, 300 MHz): δ (ppm) 0.86-0.93 (2H, m), 1.13-1.17 (3H, m), 1.47-1.49 (2H, m), 1.61-1.65 (2H, m), 1.92 (2H, t, J=6.9 Hz, CH2CO), 2.96 (2H, m, N(CHH)2), 3.93 (1H, d, J=12.9 Hz, NCHH), 4.36 (1H, d, J=12.9 Hz, NCHH), 7.19 (1H, d, J=6.9 Hz, NCONH), 7.30-7.40 (5H, m, ArH), 8.66 (1H, s, OH), 10.34 (1H, s, NH).
MF C16H23NO3, MW 305.37
1H NMR (DMSO-d6, 300 MHz): 6 ?(ppm) 1.04-1.28 (5H, m), 1.42 (2H, m), 1.66 (2H, d, J=12.3 Hz), 1.86 (2H, t, J=6.9 Hz, CH2CO), 2.46 (2H, m, N(CHH)2), 3.73 (2H, d, J=12.3 Hz, N(CHH)2), 7.68-7.72 (3H, m, ArH), 8.12 (2H, t, J=6.5 Hz, ArH), 8.29 (1H, d, J=8.1 Hz, ArH), 8.64 (1H, d, J=6.5 Hz, ArH), 8.68 (1H, s, OH), 10.28 (1H, s, NH).
MF, C19H24N2O4S, MW 376.47
1H NMR (DMSO-d6, 300 MHz): δ (ppm) 1.12 (5H, m), 1.42 (2H, m), 1.67-1.70 (2H, m), 1.86 (2H, t, J=6.9 Hz, CH2CO), 2.22 (2H, m, N(CHH)2), 3.70 (2H, d, J=10.8 Hz, N(CHH)2), 7.70-7.77 (3H, m, ArH), 8.09 (1H, d, J=8.1 Hz, ArH), 8.16-8.23 (2H, m, ArH), 8.64 (1H, s, ArH), 8.63 (1H, s, OH), 10.27 (1H, s, NH).
MF C19H24N2O4S, MW 376.47
1H NMR (DMSO-d6, 400 MHz): δ (ppm) 0.96-1.16 (2H, m), 1.16-1.32 (2H, m), 1.41-1.58 (3H, m), 1.58-1.83 (2H, m), 1.94 (2H, t, J=7.2 Hz, CH2CO), 2.62-2.83 (1H, m, NCHH), 2.92-3.12 (1H, m, NCHH), 3.57-3.70 (1H, m, NCHH), 4.40-4.54 (1H, m, NCHH), 7.09 (1H, d, J=7.6 Hz, ArH), 7.42 (1H, d, J=7.6 Hz, ArH), 7.51-7.59 (2H, m, ArH), 7.59-7.66 (1H, m, ArH), 7.81-7.88 (2H, m, ArH), 7.97 (2H, d, J=6.8 Hz, ArH), 8.69 (1H, s, OH), 10.39 (1H, s, NH).
MF C23H27N3O4, MW 409.48
1H NMR (DMSO-d6, 300 MHz): δ (ppm) 1.03-1.34 (4H, m), 1.50-1.59 (3H m), 1.76 (2H, d, J=12.6 Hz), 1.94 (2H, t, J=7.3 Hz), 2.83 (1H, brs), 4.17-4.29 (1H, brs), 4.29-4.50 (1H, brs), 7.32-7.36 (2H, m, ArH), 7.44 (1H, m, ArH), 7.67 (1H, d, ArH, J=8.4 Hz), 8.66 (1H, s, OH), 10.34 (1H, s, NH).
MF C18H22N2O4, MW 330.39
1H NMR (DMSO-d6, 400 MHz): δ (ppm) 1.18-1.26 (4H, m), 1.48-1.82 (5H, m), 1.94 (2H, t, J=7.2 Hz, CH2CO), 2.70-3.20 (2H, m), 3.60-3.75 (1H, m, N(CHH)2), 3.90 (3H, s, OCH3), 4.40-4.60 (1H, m, N(CHH)2), 7.24 (1H, d, J=7.2 Hz, ArH), 7.38 (1H, s, ArH), 7.45 (1H, d, J=7.2 Hz, ArH), 7.85-7.95 (3H, m, ArH), 8.65 (1H, s, OH), 10.32 (1H, s, NH).
MF C21H26N2O4, MW: 370.44
1H NMR (DMSO-d6, 400 MHz): δ (ppm) 0.95-1.25 (4H, m), 1.40-1.60 (4H, m), 1.68 (1H, d, J=12.3 Hz), 1.95 (2H, t, J=7.2 Hz, CH2CO), 2.75 (2H, t, J=12.3 Hz, N(CHH)2), 4.10 (2H, d, J=13.1 Hz, N(CHH)2), 6.72 (1H, m, ArH), 7.25 (2H, m, ArH), 7.45 (1H, d, J=12.2 Hz, ArH), 8.61 (2H, s, OH, NHAr), 10.31 (1H, s, NH).
MF C16H22FN3O3, MW: 322.36
1H NMR (DMSO-d6, 400 MHz): δ (ppm) 0.40-1.30 (4H, m), 1.22-1.60 (4H, m), 1.85 (1H, d, J=13.4 Hz), 1.92 (2H, t, J=7.2 Hz, CH2CO), 2.30 (3H, s, CH3), 2.70-3.40 (3H, m, N(CHH)2), 4.70 (1H, t, J=13.4 Hz, N(CHH)2), 7.40-7.58 (3H, m, ArH), 7.65 (1H, d, J=8.4 Hz, ArH), 7.68 (1H, d, J=8.4 Hz, ArH), 7.84 (1H, d, J=8.4 Hz, ArH), 8.61 (1H, s, OH), 10.29 (1H, s, NH).
MF: C21H26N2O3, MW: 354.44
1H NMR (DMSO-d6, 400 MHz): δ (ppm) 0.95-1.22 (4H, m), 1.40-1.60 (4H, m), 1.68 (1H, m), 1.95 (2H, t, J=7.2 Hz, CH2CO), 2.75 (2H, t, J=12.1 Hz, N(CHH)2), 4.10 (2H, d, J=13.2 Hz, N(CHH)2), 7.35 (2H, d, J=8.9 Hz, ArH), 7.42 (2H, d, J=8.9 Hz, ArH), 8.60 (1H, m, NHAr), 8.54 (1H, s, OH), 10.31 (1H, s, NH).
MF: C16H22BrN3O3, MW: 384.27
1H NMR (DMSO-d6, 400 MHz): δ (ppm) 1.02 (2H, dq, J=3.2 and 12.4 Hz), 1.14-1.29 (2H, m), 1.37-1.48 (1H, m) 1.53 (2H, quin, J=7.4 Hz), 1.62-1.72 (2H, m), 1.95 (2H, t, J=7.2 Hz, CH2CO), 2.75 (2H, m, N(CHH)2), 4.10 (2H, m, N(CHH)2), 7.26 (2H, d, J=8.8 Hz, ArH), 7.50 (2H, d, J=8.8 Hz, ArH), 8.54 (1H, m, NCONH), 8.63 (1H, bs, OH), 10.31 (1H, bs, NHOH).
MF C16H22ClN3O3, MW 339.82
MF C16H22ClN3O3, MW 339.82
MF C16H22FN3O3, MW 323.36
1H NMR (DMSO-d6, 400 MHz): δ (ppm) 1.02 (2H, dq, J=3.6 and 12.0 Hz), 1.12-1.28 (2H, m), 1.34-1.47 (1H, m) 1.53 (2H, quin, J=7.4 Hz), 1.60-1.71 (2H, m), 1.95 (2H, t, J=7.2 Hz, CH2CO), 2.72 (2H, m, N(CHH)2), 3.71 (3H, s, OCH3), 4.08 (2H, m, N(CHH)2), 6.81 (2H, d, J=9.2 Hz, ArH), 7.33 (2H, d, J=9.2 Hz, ArH), 8.24 (1H, m, NCONH), 8.63 (1H, bs, OH), 10.31 (1H, bs, NHOH).
MF C17H25N3O4, MW 335.40
MF C17H25N3O4, MW 335.40
1H NMR (DMSO-d6, 400 MHz): δ (ppm) 1.02 (2H, dq, J=3.2 and 12.0 Hz), 1.12-1.28 (2H, m), 1.33-1.47 (1H, m) 1.53 (2H, quin, J=7.6 Hz), 1.61-1.71 (2H, m), 1.95 (2H, t, J=7.2 Hz, CH2CO), 2.23 (3H, s, CH3), 2.73 (2H, m, N(CHH)2), 4.09 (2H, m, N(CHH)2), 7.02 (2H, d, J=8.0 Hz, ArH), 7.33 (2H, d, J=8.0 Hz, ArH), 8.30 (1H, m, NCONH), 8.63 (1H, bs, OH), 10.31 (1H, bs, NHOH).
MF C17H25N3O3, MW 319.40
MF C17H25N3O3, MW 319.40
1H NMR (DMSO-d6, 300 MHz): δ (ppm) 0.86-0.91 (2H, m), 1.08-1.40 (3H m), 1.50-1.59 (2H, m), 1.75 (1H, d, J=12.1 Hz), 1.96 (2H, t, J=7.3 Hz), 2.91 (3H, brs, N(CHH)2), 4.27 (2H, brs), 7.41-7.46 (1H, m, ArH), 7.68 (1H, s, ArH), 7.91-8.04 (2H, m, ArH), 8.63 (1H, s, OH), 10.34 (1H, s, NH).
MF C18H22N2O3S, MW 346.44
1H NMR (DMSO-d6, 400 MHz): δ (ppm) 0.95-1.25 (4H, m), 1.40-1.60 (4H, m), 1.68 (1H, d, J=12.3 Hz), 1.95 (2H, t, J=7.2 Hz, CH2CO), 2.75 (2H, t, J=12.3 Hz, N(CHH)2), 4.10 (2H, d, J=13.1 Hz, N(CHH)2), 6.72 (1H, m, ArH), 7.25 (2H, m, ArH), 7.45 (1H, d, J=12.2 Hz, ArH), 8.61 (2H, s, OH, NHAr), 10.31 (1H, s, NH).
MF: C16H22FN3O3, MW: 322.363
1H NMR (DMSO-d6, 400 MHz): δ (ppm) 0.93-1.03 (2H, m), 1.15-1.51 (5H, m), 1.66 (2H, d, J=13.2 Hz), 1.93 (2H, t, J=7.2 Hz), 2.78 (2H, brs), 3.99 (2H, d, J=13.1 Hz), 5.07 (2H, s, CH2Ph), 7.36 (5H, s, ArH), 8.62 (1H, s, OH), 10.31 (1H, s, NH).
MF: C17H24N2O4, MW: 320.38
1H NMR (DMSO-d6, 400 MHz): δ (ppm) 0.95-1.25 (4H, m), 1.49-1.57 (3H, m), 1.66-1.75 (2H, m), 1.95 (2H, t, J=7.2 Hz, CH2CO), 2.62 (1H, t, J=13.3 Hz, N(CHH)2), 3.06 (1H, t, J=12.8 Hz, N(CHH)2), 4.47 (1H, d, J=12.7 Hz, N(CHH)2), 4.26 (1H, d, J=11.7 Hz, N(CHH)2), 7.23-7.27 (2H, m, ArH), 7.37-7.48 (4H, m, ArH), 7.70-7.72 (2H, m, ArH), 8.63 (1H, s, OH), 10.31 (1H, s, NH).
MF: C18H24N2O3, MW: 316.39
1H NMR (DMSO-d6, 400 MHz): δ (ppm) 1.10 (2H, q), 1.19-1.28 (2H, m), 1.49-1.57 (3H, m), 1.70 (2H, d, J=12.5 Hz), 1.95 (2H, t, J=7.2 Hz), 2.62 (2H, t, J=13.3 Hz, N(CH2)2), 4.26 (2H, d, J=11.7 Hz, N(CH2)2), 7.14 (1H, t, ArH, J=7.4 Hz), 7.22 (1H, t, ArH, J=7.22 Hz), 7.49 (1H, d, ArH, J=8.1 Hz), 7.67 (2H, m, ArH), 8.63 (1H, s, OH), 10.31 (1H, s, NH).
MF C19H25N3O3, MW: 343.42
1H NMR (DMSO-d6, 400 MHz): δ (ppm) 0.70-1.25 (4H, m), 1.40-1.70 (7H, m), 1.79 (2H, q, J=7.6 Hz, CH2CH2CH2), 1.95 (2H, t, J=7.2 Hz, CH2CO), 2.3 (2H, t, J=7.3 Hz, CH2CO), 2.6 (2H, t, J=7.3 Hz, CH2Ar), 2.91 (1H, t, J=13.0 Hz, N(CHH)2), 3.75 (1H, d, J=13.0 Hz, N(CHH)2), 4.40 (1H, d, J=13.0 Hz, N(CHH)2), 7.15-7.22 (5H, m, ArH), 10.31 (1H, s, NH).
MF: C19H28N2O3, MW: 332.43
1H NMR (DMSO-d6, 400 MHz): δ (ppm) 0.70-1.23 (4H, m), 1.30-1.70 (6H, m), 1.95 (2H, t, J=7.2 Hz, CH2CO), 2.90 (1H, t, J=12.4 Hz, N(CHH)2), 3.75 (2H, s, CH2Ind), 4.01 (1H, d, J=12.4 Hz, N(CHH)2), 4.40 (1H, d, J=12.4 Hz, COCH2Ind), 6.95 (1H, t, J=7.6 Hz, ArH), 7.08 (1H, t, J=7.6 Hz, ArH), 7.18 (1H, s, ArH), 7.32 (1H, d, J=7.6 Hz, ArH), 7.58 (1H, d, J=7.6 Hz, ArH), 10.31 (1H, s, NH), 10.70 (1H, s, NHInd).
MF: C19H25N3O3, MW: 332.43
1H NMR (DMSO-d6, 400 MHz): δ (ppm) 0.70-1.23 (4H, m), 1.30-1.70 (5H, m), 1.95 (2H, t, J=7.3 Hz, CH2CO), 2.3 (3H, s, CH3), 2.55 (1H, t, J=12.2 Hz, N(CHH)2), 3.05 (1H, t, J=12.2 Hz, N(CHH)2), 3.6 (2H, s, CH2Ar), 4.00 (1H, d, J=12.2 Hz, N(CHH)2), 4.35 (1H, d, J=12.2 Hz, N(CHH)2), 7.40-7.55 (3H, m, ArH), 7.75-7.85 (2H, m, ArH), 10.31 (1H, s, NH).
MF: C21H27N3O4, MW: 385.45
1H NMR (DMSO-d6, 400 MHz): δ (ppm) 0.70-1.23 (4H, m), 1.30-1.70 (5H, m), 1.95 (2H, t, J=7.3 Hz, CH2CO), 2.55 (1H, t, J=12.2 Hz, N(CHH)2), 3.05 (1H, t, J=12.2 Hz, N(CHH)2), 3.9 (2H, s, CH2Ar), 4.05 (1H, d, J=12.2 Hz, N(CHH)2), 4.35 (1H, d, J=12.2 Hz, N(CHH)2), 7.40-7.55 (4H, m, ArH), 7.75-7.85 (2H, m, ArH), 8.4 (1H, s, OH), 10.31 (1H, s, NH).
MF: C20H25N3O3S, MW: 387.50
1H NMR (DMSO-d6, 400 MHz): δ (ppm) 0.70-1.23 (4H, m), 1.30-1.70 (5H, m), 1.95 (2H, t, J=7.3 Hz, CH2CO), 2.55 (1H, t, J=12.2 Hz, N(CHH)2), 3.05 (1H, t, J=12.2 Hz, N(CHH)2), 4.05 (1H, d, J=12.2 Hz, N(CHH)2), 4.15 (2H, s, CH2Ar), 4.35 (1H, d, J=12.2 Hz, N(CHH)2), 7.38 (1H, t, J=7.32 Hz, ArH), 7.65 (1H, t, J=7.32 Hz, ArH), 7.42 (1H, d, J=7.32 Hz, ArH), 7.58 (1H, d, J=7.32 Hz, ArH), 8.45 (1H, bs, OH), 10.31 (1H, s, NH).
MF: C18H23N3O4, MW: 387.50
1H NMR (DMSO-d6, 400 MHz): δ (ppm) 0.82-1.00 (2H, m), 1.09-1.21 (2H, m), 1.28-1.43 (1H, m), 1.49 (2H, quin, J=7.6 Hz), 1.54-1.64 (2H, m), 1.91 (2H, t, J=7.2 Hz, CH2CO), 2.62 (2H, m, N(CHH)2), 3.94 (2H, m, N(CHH)2), 4.18 (2H, s, PhCH2), 7.05 (1H, m, NCONH), 7.24 (2H, d, J=8.0 Hz, ArH), 7.35 (2H, d, J=8.0 Hz, ArH), 8.62 (1H, bs, OH), 10.32 (1H, s, NHOH).
MF C17H24ClN3O3, MW 353.84
1H NMR (DMSO-d6, 400 MHz): δ (ppm) 1.02-1.18 (2H, m), 1.18-1.33 (2H, m), 1.40-1.52 (1H, m) 1.57 (2H, m), 1.66-1.77 (2H, m), 1.97 (2H, t, J=7.2 Hz, CH2CO), 2.84 (2H, m, N(CHH)2), 4.18 (2H, m, N(CHH)2), 7.38-7.56 (4H, m), 7.72 (1H, t, J=8.0 Hz, ArH), 7.88-7.96 (2H, m, ArH), 8.51 (1H, s, NCONH), 8.64 (1H, bs, OH), 10.33 (1H, s, NHOH).
MF C20H25N3O3, MW 355.43
1H NMR (DMSO-d6, 400 MHz): δ (ppm) 0.97-1.12 (2H, m), 1.16-1.30 (2H, m), 1.38-1.50 (1H, m) 1.55 (2H, m), 1.63-1.75 (2H, m), 1.96 (2H, t, J=7.2 Hz, CH2CO), 2.80 (2H, m, N(CHH)2), 4.17 (2H, m, N(CHH)2), 7.34 (1H, t, J=7.4 Hz, ArH), 7.42 (1H, t, J=7.4 Hz, ArH), 7.62 (1H, d, J=8.8 Hz, ArH), 7.70-7.83 (3H, m, ArH), 8.02 (1H, s, ArH), 8.64 (2H, s, NCONH and OH), 10.32 (1H, s, NHOH).
MF C20H25N3O3, MW 355.43
MF C17H25N3O4, MW 335.39
MF C16H22ClN3O3, MW 339.82
1H NMR (DMSO-d6, 400 MHz): δ (ppm) 0.70-1.23 (4H, m), 1.30-1.70 (5H, m), 1.95 (2H, t, J=7.3 Hz, CH2CO), 2.75 (2H, t, J=12.2 Hz, N(CHH)2), 3.95 (2H, d, J=12.2 Hz, N(CHH)2), 4.15 (2H, s, CH2Ar), 7.00-7.38 (5H, m, ArH+NH amide), 8.35 (1H, bs, OH), 10.31 (1H, s, NH).
MF: C17H24ClN3O3, MW: 387.49
1H NMR (DMSO-d6, 400 MHz): δ (ppm) −0.23-0.11, 0.61-0.76 (1H, q, J=11.7 Hz), 0.89-1.67 (8H, m), 1.95 (2H, dd J=7.3 and 15.7 Hz), 2.82-3.08 (2H, m, CH2Ph), 3.64 (1H, d, J=13.4 Hz, N(CHH)2), 4.35 (1H, d, J=13.1 Hz, N(CHH)2), 4.65 (1H, dd, J=7.0 and 14.7 Hz), 7.20-7.37 (5H, m, ArH), 8.15 (3H, brs, NH3+), 8.63 (1H, bs, OH), 10.31 (1H, s, NH).
MF C18H27N3O3, MW: 333.42
MF: C18H27N3O3, MW: 333.42
MF: C18H27N3O4, MW: 349.42
MF: C18H27N3O4, MW: 349.42
1H NMR (DMSO-d6, 400 MHz): δ (ppm) 0.87-1.02 (2H, m), 1.12-1.25 (2H, m), 1.30-1.45 (1H, m), 1.51 (2H, m), 1.56-1.65 (2H, m), 1.94 (2H, t, J=7.0 Hz, CH2CO), 2.63 (2H, m, N(CHH)2), 3.73 (3H, s, OCH3), 3.96 (2H, m, N(CHH)2), 4.15 (2H, d, J=5.2 Hz, PhCH2), 6.86 (2H, d, J=8.0 Hz, ArH), 6.87 (1H, m, NCONH), 7.17 (2H, d, J=8.0 Hz, ArH), 8.62 (1H, s, OH), 10.30 (1H, s, NH).
MF C1-8H27N3O4, MW 349.42
1H NMR (DMSO-d6, 400 MHz): δ (ppm) 0.89-1.05 (2H, m), 1.13-1.26 (2H, m), 1.32-1.46 (1H, m), 1.52 (2H, quin, J=7.4 Hz), 1.56-1.70 (2H, m), 1.94 (2H, t, J=7.0 Hz, CH2CO), 2.66 (2H, m, N(CHH)2), 3.97 (2H, m, N(CHH)2), 4.28 (2H, d, J=5.2 Hz, PhCH2), 6.95 (1H, m, NCONH), 7.09-7.20 (2H, m, ArH), 7.23-7.34 (2H, m, ArH), 8.65 (1H, s, OH), 10.31 (1H, s, NH).
MF C17H24FN3O3, MW 337.39
MF C17H24FN3O3, MW 337.39
MF C17H24ClN3O3, MW 353.84
1H NMR (DMSO-d6, 400 MHz): δ (ppm) 0.93-1.08 (2H, m), 1.13-1.34 (2H, m), 1.34-1.47 (1H, m), 1.53 (2H, m), 1.60-1.71 (2H, m), 1.95 (2H, t, J=7.0 Hz, CH2CO), 2.71 (2H, m, N(CHH)2), 2.84 (6H, s, 2×CH3), 4.08 (2H, m, N(CHH)2), 6.50-6.87 (2H, m, ArH), 7.18-7.42 (2H, m, ArH), 8.15 (1H, m, NCONH), 8.63 (1H, bs, OH), 10.35 (1H, s, NH). MF, C18H28N4O3 MW 348.44
MF C16H24N4O3, MW 320.38
MF C18H27N3O3, MW 333.42
MF C18H27N3O3, MW 333.42
1H NMR (DMSO-d6, 400 MHz): δ (ppm) 0.95 (2H, dq, J=3.2 and 12.0 Hz), 1.12-1.26 (2H, m), 1.30-1.44 (1H, m), 1.51 (2H, quin, J=7.4 Hz), 1.55-1.66 (2H, m), 1.94 (2H, t, J=7.0 Hz, CH2CO), 2.27 (3H, s, CH3), 2.63 (2H, m, N(CHH)2), 3.96 (2H, m, N(CHH)2), 4.18 (2H, d, J=4.8 Hz, PhCH2), 6.91 (1H, m, NCONH), 7.03-7.17 (4H, m, ArH), 8.60 (1H, bs, OH), 10.30 (1H, s, NH).
MF C18H27NO3, MW 333.42
1H NMR (DMSO-d6, 400 MHz): δ (ppm) 0.90-1.05 (2H, m), 1.11-1.27 (2H, m), 1.32-1.46 (1H, m), 1.53 (2H, m), 1.58-1.69 (2H, m), 1.95 (2H, t, J=7.0 Hz, CH2CO), 2.70 (2H, m, N(CHH)2), 3.97 (2H, m, N(CHH)2), 4.41 (2H, d, J=5.2 Hz, PhCH2), 7.26 (1H, t, J=7.0 Hz, NCONH), 7.72 (2H, d, J=5.4 Hz, ArH), 8.74 (2H, d, J=5.4 Hz, ArH), 10.31 (1H, s, NH).
MF C16H24N4O3, MW 320.39
1H NMR (DMSO-d6, 400 MHz): δ (ppm) 0.95-1.23 (4H, m), 1.30-1.70 (5H, m), 1.95 (2H, t, J=7.3 Hz, CH2CO), 2.65 (2H, t, J=12.4 Hz, N(CHH)2), 4.0 (2H, d, J=12.4 Hz, N(CHH)2), 4.70 (2H, s, CH2Ar), 6.98 (1H, s, NHCH), 7.40-7.60 (4H, m, ArH), 7.80 (1H, d, J=7.88 Hz, ArH), 7.92 (1H, d, J=7.8 Hz, ArH), 8.18 (1H, d, J=7.8 Hz, ArH), 8.60 (1H, bs, OH), 10.32 (1H, s, NH).
MF C21H27N3O3, MW: 369.46
1H NMR (DMSO-d6, 400 MHz): δ (ppm) 0.95-1.23 (4H, m), 1.30-1.70 (5H, m), 1.95 (2H, t, J=7.30 Hz, CH2CO), 2.65 (2H, t, J=12.4 Hz, N(CHH)2), 4.0 (2H, d, J=12.4 Hz, N(CHH)2), 4.30 (2H, s, CH2Ar), 7.20 (1H, s, NHCH), 7.45-7.55 (3H, m, ArH), 7.70 (1H, s, ArH) 7.88-7.85 (3H, m, ArH), 8.30 (1H, bs, OH), 10.28 (1H, s, NH).
MF C2, H27N3O3, MW: 369.457
1H NMR (DMSO-d6, 400 MHz): δ (ppm) 0.95-1.23 (4H, m), 1.30-1.65 (5H, m), 1.95 (2H, t, J=7.25 Hz, CH2CO), 2.64 (2H, t, J=12.3 Hz, N(CHH)2), 4.0 (2H, d, J=12.3 Hz, N(CHH)2), 4.30 (2H, s, CH2Ar), 7.00 (1H, s, NHCH), 7.32 (3H, t, J=8.92 Hz, ArH), 7.45 (2H, t, J=8.92 Hz, ArH), 7.60 (2H, J=7.56 Hz, ArH), 7.65 (2H, J=7.56 Hz, ArH), 8.60 (1H, bs, OH), 10.30 (1H, s, NH).
MF C23H29N3O3, MW: 395.50
1H NMR (DMSO-d6, 400 MHz): δ (ppm) 0.95-1.23 (4H, m), 1.30-1.75 (5H, m), 1.95 (2H, t, J=7.2 Hz, CH2CO), 2.62 (2H, t, J=12.4 Hz, N(CHH)2), 4.0 (2H, d, J=12.4 Hz, N(CHH)2), 4.22 (2H, S, CH2Ar), 6.94-7.00 (5H, m, ArH), 7.12 (1H, t, J=7.5 Hz, NHCH), 7.26 (2H, m, ArH), 7.38 (2H, d, J=7.4 Hz, ArH), 8.50 (1H, bs, OH), 10.32 (1H, s, NH).
MF C23H29N3O4, MW: 411.50
1H NMR (DMSO-d6, 400 MHz): δ (ppm) 0.75-1.23 (4H, m), 1.30-1.65 (5H, m), 1.95 (2H, t, J=7.30 Hz, CH2CO), 2.60 (2H, t, J=12.5 Hz, N(CHH)2), 2.72 (2H, t, J=7.25 Hz, CH2Ph), 3.40 (2H, m, CH2NH), 3.80 (2H, d, J=12.5 Hz, N(CHH)2), 6.50 (1H, s, CH2NH), 7.25-7.60 (5H, m, ArH), 8.50 (1H, bs, OH), 10.32 (1H, s, NH).
MF C18H27N3O3, MW, 333.42
1H NMR (DMSO-d6, 400 MHz): δ (ppm) 0.75-1.23 (4H, m), 1.30-1.85 (7H, m), 1.95 (2H, t, J=7.3 Hz, CH2CO), 2.50-2.70 (4H, m, CH2Ph and CH2N), 3.20 (2H, m, CH2NH), 3.95 (2H, d, J=12.6 Hz, N(CHH)2), 6.35 (1H, s, CH2NH), 7.25-7.60 (5H, m, ArH), 8.50 (1H, bs, OH), 10.32 (1H, s, NH).
MF C19H29N3O3, MW: 347.45
1H NMR (DMSO-d6, 400 MHz): δ (ppm) −0.13-0.02, 0.63-0.75 (1H, dd, 1H, J=13.0 Hz, J=24.9 Hz), 0.99-1.01 (3H, m), 1.33-1.71 (5H, m), 1.95 (2H, dd J=7.3 and 15.7 Hz), 2.55 (1H, m), 2.86-3.05 (2H, m, CH2Ph), 3.64-3.76 (1H, m, N(CHH)2), 4.35 (1H, d, J=13.8 Hz, N(CHH)2), 4.61-4.68 (1H, m, N(CHH)2), 7.23-7.27 (2H, t, ArH, J=7.7 Hz), 7.40-7.44 (2H, dd, J=6.1 Hz, J=8.2 Hz, ArH), 8.14 (3H, bs, NH3+), 8.62 (1H, bs, OH), 10.31 (1H, s, NH).
MF: C18H26ClN3O3, MW: 367.87
MF C18H26ClN3O3, MW: 367.87
1H NMR (DMSO-d6, 400 MHz): δ (ppm) −0.002-0.09, 0.64-0.73 (1H, dd, 1H, J=11.3 Hz, J=24.7 Hz), 1.16-1.24 (2H, m), 1.35-1.55 (4H, m), 1.62-1.72 (2H, m), 1.95 (2H, dd, J=7.8 Hz, J=16.5 Hz), 2.55 (1H, m), 2.77-2.84 (1H, t, J=12.3 Hz), 2.90-3.04 (2H, m, CH2Ph), 3.72-3.78, 3.82-3.89 (1H, d, J=13 Hz, N(CHH)2), 4.35 (1H, d, J=13.3 Hz, N(CHH)2), 4.63-4.71 (1H, m, N(CHH)2), 7.24 (1H, dt, ArH), 7.52-7.65 (2H, m, ArH), 8.14 (3H, brs, NH3+), 8.62 (1H, bs, OH), 10.31 (1H, s, NH).
MF C18H25Cl2N3O3, MW: 402.31
1H NMR (DMSO-d6, 400 MHz): δ (ppm) −0.16-0.05, 0.64-0.75 (1H, dd, J=12.2 Hz, J=23.2 Hz), 0.85-1.04 (2H, m), 1.28-1.69 (6H, m), 1.88-1.94 (2H, m), 2.83-3.03 (3H, m, CH2Ph, N(CHH)2), 3.61 (1H, t, J=11.7 Hz, N(CHH)2), 3.74 (3H, s, OCH3), 4.36 (1H, d, J=12.4 Hz, N(CHH)2), 4.58 (1H, brs, N(CHH)2), 6.89-6.92 (2H, m, ArH), 7.11-7.17 (2H, t, ArH, J=8.9 Hz), 8.13 (3H, brs, NH3+), 8.62 (1H, bs, OH), 10.31 (1H, s, NH).
MF C19H29N3O4, MW: 363.45
1H NMR (DMSO-d6, 400 MHz): δ (ppm) 1.00-1.23 (4H, m), 1.50-1.60 (2H, m, CH2NH), 1.63 (3H, s, CH3), 1.80 (2H, m, CH2NH), 1.95 (2H, t, J=7.35 Hz, CH2CO), 2.95 (2H, m, CH2NH), 3.10 (1H, d, J=7.00 Hz, CH2Ph), 3.30 (1H, d, J=7.00 Hz, CH2Ph), 4.30 (2H, m, CH2NH), 7.20-7.40 (5H, m, ArH), 8.00 (3H, s, NH3+), 8.60 (1H, bs, OH), 10.32 (1H, s, NH).
MF C19H29N3O3, MW: 347.45
1H NMR (DMSO-d6, 400 MHz): δ (ppm) −0.50-0.30 (1H, dq, J=12.2 Hz), 0.8-1.7 (6H, m), 1.95 (2H, t, J=7.35 Hz, CH2CO), 2.7 (1H, t, J=12.4 Hz, N(CHH)2), 3.15 (2H, m, CH2In), 3.50 (1H, t, J=13.2 Hz, N(CHH)2), 3.65 (1H, t, J=13.2 Hz, N(CHH)2), 4.30 (1H, t, J=11.9 Hz, N(CHH)2), 4.60 (1H, m, CHNH), 7.00-7.15 (2H, dt, J=7.60 Hz, ArH), 7.25 (1H, m, ArH), 7.38 (1H, d, J=7.60 Hz, ArH) ArH), 7.45-7.55 (1H, d, J=7.60 Hz, ArH), 8.2 (3H, bs, NH3+), 8.60 (1H, s, OH), 10.32 (1H, s, NH), 11.0 (1H, s, NHInd).
MF C20H28N4O3, MW: 372.46
1H NMR (DMSO-d6, 400 MHz): δ (ppm) −0.50-0.30 (1H, dq, J=12.25 Hz), 0.8-1.7 (6H, m), 1.95 (2H, t, J=7.35 Hz, CH2CO), 2.7 (1H, t, J=12.4 Hz, N(CHH)2), 3.15 (2H, m, CH2In), 3.50 (1H, t, J=13.2 Hz, N(CHH)2), 3.65 (1H, t, J=13.2 Hz, N(CHH)2), 4.30 (1H, t, J=11.92 Hz, N(CHH)2), 4.60 (1H, m, CHNH), 7.00-7.15 (2H, dt, J=7.60 Hz, ArH), 7.25 (1H, m, ArH), 7.38 (1H, d, J=7.60 Hz, ArH), 7.45-7.55 (1H, d, J=7.60 Hz, ArH), 8.2 (3H, bs, NH3+), 8.60 (1H, s, OH), 10.32 (1H, s, NH), 11.0 (1H, s, NH-Ind).
MF C20H28N4O3, MW: 372.46
1H NMR (DMSO-d6, 400 MHz): δ (ppm) 0.60-1.23 (4H, m), 1.40-1.80 (5H, m), 1.95 (2H, t, J=7.27 Hz, CH2CO), 2.65 (1H, m, CH2NH), 2.95 (1H, m, CH2NH), 3.60-3.70 (2H, m, OCH2Ph), 4.50-4.70 (3H, m, CHCH2O, CHNH2), 3.80 (1H, m, CH2NH), 4.35 (1H, m, CH2NH), 7.20-7.40 (5H, m, ArH), 8.20 (3H, s, NH3+), 8.60 (1H, bs, OH), 10.36 (1H, s, NH).
MF C19H29N3O4, MW: 347.45
1H NMR (DMSO-d6, 400 MHz): δ (ppm) 0.0-0.80 (1H, dq, J=12.23 Hz), 0.7-1.2 (2H, m), 1.30 (9H, s, O(CH3)3), 1.30-1.70 (5H, m), 1.95 (2H, q, J=7.80 Hz, CH2CO), 2.2 (1H, t, J=11.0 Hz, N(CHH)2), 2.45 (1H, t, J=11.0 Hz, N(CHH)2), 2.80-3.00 (2H, m, CH2Ph), 3.60 (1H, m, N(CHH)2), 4.35 (1H, d, J=12.6 Hz, N(CHH)2), 4.65 (1H, m, CHNH), 6.90-6.96 (2H, d, J=7.08 Hz, ArH), 7.10-7.18 (2H, d, J=7.08 Hz, ArH), 8.2 (3H, bs, NH3+), 8.00 (1H, s, OH), 10.32 (1H, s, NH).
MF C22H35N3O4, MW: 372.46
1H NMR (DMSO-d6, 400 MHz): δ (ppm) 0.70-1.23 (4H, m), 1.40-1.80 (5H, m), 1.95 (2H, t, J=7.27 Hz, CH2CO), 2.65-3.10 (4H, m, CH2NH, CH2Ph), 3.75 (1H, t, J=12.39 Hz, CH2NH), 3.85 (2H, d, J=8.74 Hz, SCH2Ph), 4.35 (1H, d, J=13.36 Hz, CH2NH), 4.55 (1H, m, CH2NH), 7.20-7.40 (5H, m, ArH), 8.20 (3H, s, NH3+), 8.60 (1H, bs, OH), 10.36 (1H, s, NH).
MF C19H29N3O3S, MW 379.517
1H NMR (DMSO-d6, 400 MHz): δ (ppm) 0.98-1.11 (2H, m), 1.15-1.31 (2H, m), 1.39-1.62 (3H, m), 1.62-1.76 (2H, m), 1.95 (2H, t, J=7.0 Hz, CH2CO), 2.82 (2H, m, N(CHH)2, 4.13 (2H, m, N(CHH)2), 7.66 (1H, m, ArH), 8.23 (1H, d, J=8.4 Hz, ArH), 8.34 (1H, d, J=4.4 Hz, ArH), 8.91 (1H, m, ArH), 9.08 (1H, s, NCONH), 10.32 (1H, s, NH).
MF C15H22N4O3, MW 306.36
1H NMR (DMSO-d6, 400 MHz): δ (ppm) 0.95 (2H, dq, J=3.2 and 12.0 Hz), 1.11-1.23 (2H, m), 1.32-1.46 (1H, m), 1.51 (2H, quin, J=7.5 Hz), 1.56-1.71 (2H, m), 1.94 (2H, t, J=7.0 Hz, CH2CO), 2.67 (2H, m, N(CHH)2, 3.95 (2H, m, N(CHH)2), 4.34 (2H, d, J=3.9 Hz, PhCH2), 7.18 (1H, s, NCONH), 7.73-7.84 (1H, m, ArH), 8.12-8.22 (1H, m, ArH), 8.65-8.72 (2H, m, ArH), 8.46 (1H, bs, OH), 10.32 (1H, s, NH).
MF C16H24N4O3, MW 320.39
MF C16H24N4O3, MW 320.39
1H NMR (DMSO-d6, 400 MHz): δ (ppm) 1.08 (2H, dq, J=3.2 and 12.0 Hz), 1.18-1.30 (2H, m), 1.40-1.50 (1H, m), 1.55 (2H, m), 1.64-1.74 (2H, m), 1.96 (2H, t, J=7.0 Hz, CH2CO), 2.82 (2H, m, N(CHH)2, 4.12 (2H, m, N(CHH)2), 7.09-7.25 (4H, m, ArH), 8.44 (1H, s, OH), 10.31 (1H, s, NH).
MF C16H24N4O3, MW 320.39
1H NMR (DMSO-d6, 400 MHz): δ (ppm) 0.94 (2H, dq, J=3.2 and 12.0 Hz), 1.12-1.23 (2H, m), 1.30-1.45 (1H, m), 1.51 (2H, quin, J=7.6 Hz), 1.56-1.65 (2H, m), 1.94 (2H, t, J=7.0 Hz, CH2CO), 2.62 (2H, m, N(CHH)2), 2.95 (6H, s, 2×CH3), 3.96 (2H, m, N(CHH)2), 4.15 (2H, d, J=5.8 Hz, PhCH2), 6.90 (1H, s, NCONH), 7.19 (4H, m, ArH), 10.31 (1H, s, NH).
MF C19H30N4O3, MW 362.47
MF C16H22FN3O, MW 323.36
MF C17H25N3O3, MW 319.40
1H NMR (DMSO-d6, 400 MHz): δ (ppm) 0.95 (2H, dq, J=3.2 and 12.4 Hz), 1.14-1.24 (2H, m), 1.31-1.45 (1H, m), 1.51 (2H, quin, J=7.4 Hz), 1.58-1.69 (2H, m), 1.94 (2H, t, J=7.0 Hz, CH2CO), 2.63-2.74 (2H, m, N(CHH)2), 2.67 (3H, s, CH3), 3.57 (2H, m, N(CHH)2), 4.31 (2H, s, PhCH2), 7.22-7.30 (3H, m, ArH), 7.32-7.39 (2H, m, ArH), 8.63 (1H, s, OH), 10.31 (1H, s, NH).
MF C18H27NO3, MW 333.42
1H NMR (DMSO-d6, 400 MHz): δ (ppm) 0.70-1.20 (4H, m), 1.40-1.70 (5H, m), 1.95 (2H, t, J=7.27 Hz, CH2CO), 2.55 (1H, t, J=12.3 Hz, CH2NH), 2.95 (1H, t, J=12.3 Hz, CH2NH), 3.58 (2H, s, CH2Ind), 3.70 (1H, d, J=12.3 Hz, CH2NH), 3.80-3.95 (2H, m, CH2NH), 4.30 (1H, d, J=12.3 Hz, CH2NH), 6.95-7.10 (2H, dt, J=7.36 Hz, ArH), 7.25 (1H, s, ArH), 7.35 (1H, d, J=7.4 Hz, ArH), 7.55 (1H, d, J=7.4 Hz, ArH), 7.80 (1H, m, CH2NH), 8.60 (1H, bs, OH), 10.36 (1H, s, NH), 10.85 (1H, s, NHInd).
MF: C21H28N4O4, MW: 400.47
1H NMR (DMSO-d6, 400 MHz): δ (ppm) 0.70-1.20 (4H, m), 1.40-1.80 (5H, m), 1.95 (2H, t, J=7.30 Hz, CH2CO), 2.55 (1H, t, J=10.9 Hz, CH2NH), 3.00 (1H, t, J=10.9 Hz, CH2NH), 3.90 (1H, d, J=10.9 Hz, CH2NH), 4.15 (2H, s, CH2Gly), 4.40 (1H, d, J=10.9 Hz, CH2NH), 7.40-7.50 (2H, m, ArH), 7.95-8.15 (2H, d, J=7.4 Hz, ArH), 8.65 (1H, s, OH), 8.65 (1H, s, NHCH), 10.36 (1H, s, NH).
MF: C20H25N3O4S, MW: 403.49
1H NMR (DMSO-d6, 400 MHz): δ (ppm) 0.75-1.25 (4H, m), 1.40-1.80 (5H, m), 1.95 (2H, t, J=7.3 Hz, CH2CO), 2.60 (1H, t, J=10.9 Hz, CH2NH), 3.05 (1H, t, J=10.9 Hz, CH2NH), 3.90 (1H, d, J=10.9 Hz, CH2NH), 4.15 (2H, d, J=5.8 Hz, CH2Gly), 4.40 (1H, d, J=10.9 Hz, CH2NH), 7.55-7.65 (4H, m, ArH), 7.95-8.05 (2H, m, ArH), 8.50 (1H, t, J=5.6 Hz, NHCH2), 8.65 (1H, s, OH), 10.36 (1H, s, NH).
MF: C22H27N3O4, MW: 397.47
1H NMR (DMSO-d6, 400 MHz): δ (ppm) 0.75-1.25 (4H, m), 1.40-1.80 (5H, m), 1.95 (2H, t, J=7.3 Hz, CH2CO), 2.45 (3H, s, CH3), 2.60 (1H, t, J=10.9 Hz, CH2NH), 3.05 (1H, t, J=10.9 Hz, CH2NH), 3.90 (1H, d, J=10.9 Hz, CH2NH), 4.15 (2H, d, J=5.8 Hz, CH2Gly), 4.40 (1H, d, J=10.90 Hz, CH2NH), 7.55-7.65 (3H, m, ArH), 7.95-8.05 (2H, m, ArH), 8.50 (1H, s, NHCH2), 8.65 (1H, bs, OH), 10.36 (1H, s, NH).
MF C23H29N3O4, MW: 411.49
1H NMR (DMSO-d6, 400 MHz): δ (ppm) 0.86-1.02 (2H, m), 1.17 (2H, m), 1.51 (3H, m), 1.69 (2H, m), 1.94 (4H, m), 2.57-2.74 (3H, m, CH2Ph), 2.92-3.07 (1H, q, J=13.6 Hz), 3.61-3.75 (1H, m), 4.29-4.42 (2H, m), 7.21-7.32 (5H, m, ArH), 8.12 (2H, s, NH3+), 8.63 (1H, s), 10.32 (1H, s, NH).
MF: C17H24N2O4, MW: 320.38
1H NMR (DMSO-d6, 400 MHz): δ (ppm) 1.04 (2H, dq, J=3.2 and 12.0 Hz), 1.13-1.29 (2H, m), 1.37-1.48 (1H, m) 1.54 (2H, quin, J=7.4 Hz), 1.61-1.73 (2H, m), 1.95 (2H, t, J=7.2 Hz, CH2CO), 2.78 (2H, m, N(CHH)2), 4.06 (2H, m, N(CHH)2), 7.12 (1H, m, ArH), 7.27 (1H, m, ArH)), 7.37 (1H, m, ArH), 8.39 (1H, s, NCONH), 8.64 (1H, bs, OH), 10.32 (1H, s, NHOH).
MF C16H21ClFN3O3, MW 357.81
1H NMR (DMSO-d6, 400 MHz): δ (ppm) 1.03 (2H, dq, J=3.2 and 12.0 Hz), 1.14-1.29 (2H, m), 1.35-1.48 (1H, m) 1.53 (2H, m), 1.60-1.72 (2H, m), 1.95 (2H, t, J=7.2 Hz, CH2CO), 2.76 (2H, m, N(CHH)2), 4.05 (2H, m, N(CHH)2), 7.00 (1H, m, ArH), 7.21 (1H, m, ArH), 7.38 (1H, m, ArH), 8.18 (1H, s, NCONH), 8.61 (1H, bs, OH), 10.32 (1H, s, NHOH).
MF C16H21F2N3O3, MW 341.35
1H NMR (DMSO-d6, 400 MHz): δ (ppm) 1.02 (2H, dq, J=3.7 and 12.6 Hz), 1.13-1.26 (2H, m), 1.35-1.47 (1H, m) 1.53 (2H, m), 1.60-1.73 (2H, m), 1.95 (2H, t, J=7.2 Hz, CH2CO), 2.24 (3H, s, CH3), 2.74 (2H, m, N(CHH)2), 4.09 (2H, m, N(CHH)2), 7.15-7.21 (1H, m, ArH), 7.31 (1H, dd, J=2.1 and 8.3 Hz, ArH), 7.61-7.66 (1H, m, ArH), 8.50 (1H, s, OH), 10.32 (1H, s, NHOH).
MF C17H24ClN3O3, MW 353.84
1H NMR (DMSO-d6, 400 MHz): δ (ppm) 1.02 (2H, dq, J=3.7 and 12.5 Hz), 1.14-1.27 (2H, m), 1.37-1.48 (1H, m) 1.53 (2H, m), 1.61-1.74 (2H, m), 1.95 (2H, t, J=7.2 Hz, CH2CO), 2.76 (2H, m, N(CHH)2), 4.09 (2H, m, N(CHH)2), 7.17-7.34 (2H, m, ArH), 7.62 (1H, ddd, J=2.3 and 7.5 and 13.7 Hz), 8.61 (2H, bs, NCONH and OH), 10.31 (1H, s, NHOH).
MF C16H21F2N3O3, MW 341.35
1H NMR (DMSO-d6, 400 MHz): δ (ppm) 1.01 (2H, dq, J=3.5 and 12.6 Hz), 1.14-1.25 (2H, m), 1.32-1.47 (1H, m) 1.53 (2H, m), 1.61-1.71 (2H, m), 1.95 (2H, t, J=7.2 Hz, CH2CO), 2.14 (3H, s, CH3), 2.16 (3H, s, CH3), 2.72 (2H, m, N(CHH)2), 4.09 (2H, m, N(CHH)2), 6.93-6.99 (1H, m, ArH), 7.13-7.19 (1H, m, ArH), 7.21-7.25 (1H, m, ArH), 8.23 (1H, s, NCONH), 8.63 (1H, bs, OH), 10.31 (1H, s, NHOH).
MF C18H27N3O3, MW 333.42
1H NMR (DMSO-d6, 400 MHz): δ (ppm) 1.02 (2H, dq, J=3.8 and 12.6 Hz), 1.13-1.25 (2H, m), 1.36-1.48 (1H, m) 1.53 (2H, m), 1.62-1.73 (2H, m), 1.94 (2H, t, J=7.2 Hz, CH2CO), 2.76 (2H, m, N(CHH)2), 4.09 (2H, m, N(CHH)2), 7.27 (1H, d, J=9.1 Hz, ArH), 7.38-7.45 (1H, m, ArH), 7.76 (1H, dd, J=2.6 and 6.9 Hz, ArH), 8.61 (2H, bs, NCONH and OH), 10.31 (1H, s, NHOH).
MF C16H21ClFN3O3, MW 357.81
1H NMR (DMSO-d6, 400 MHz): δ (ppm) 1.04 (2H, dq, J=3.7 and 12.6 Hz), 1.14-1.27 (2H, m), 1.35-1.48 (1H, m) 1.53 (2H, m), 1.60-1.74 (2H, m), 1.95 (2H, t, J=7.2 Hz, CH2CO), 2.78 (2H, m, N(CHH)2), 4.03-4.11 (2H, m, N(CHH)2), 6.84-6.93 (1H, m, ArH), 7.17-7.26 (1H, m, ArH), 7.37-7.46 (1H, m, ArH), 8.30 (1H, s, NCONH), 8.63 (1H, s, OH), 10.33 (1H, s, NHOH).
MF C16H21F2N3O3, MW 341.35
1H NMR (DMSO-d6, 400 MHz): δ (ppm) 1.03 (2H, dq, J=3.8 and 12.6 Hz), 1.15-1.27 (2H, m), 1.37-1.48 (1H, m) 1.53 (2H, quin, J=7.4 Hz), 1.61-1.74 (2H, m), 1.95 (2H, t, J=7.2 Hz, CH2CO), 2.77 (2H, m, N(CHH)2), 4.06 (2H, m, N(CHH)2), 7.16-7.22 (1H, m, ArH), 7.38 (1H, dd, J=2.3 and 10.5 Hz, ArH), 7.42-7.49 (1H, m, ArH), 8.27 (1H, s, NCONH), 8.62 (1H, bs, OH), 10.31 (1H, s, NHOH).
MF C16H21ClFN3O3, MW 357.81
1H NMR (DMSO-d6, 400 MHz): δ (ppm) 1.03 (2H, dq, J=3.8 and 12.6 Hz), 1.14-1.28 (2H, m), 1.33-1.48 (1H, m) 1.53 (2H, m), 1.63-1.71 (2H, m), 1.95 (2H, t, J=7.2 Hz, CH2CO), 2.74 (2H, m, N(CHH)2), 3.74 (3H, s, OCH3), 3.78 (3H, s, OCH3), 4.01 (2H, m, N(CHH)2), 6.45 (1H, dd, J=2.6 and 8.7 Hz, ArH), 6.57 (1H, d, J=2.6 Hz, ArH), 7.35-7.39 (1H, m, ArH), 7.42 (1H, s, NCONH), 8.63 (1H, bs, OH), 10.31 (1H, s, NHOH).
MF C18H27N3O5, MW 365.42
1H NMR (DMSO-d6, 400 MHz): δ (ppm) −0.5-0.60 (1H, dq, J=12.20 Hz), 0.8-1.7 (8H, m), 1.95 (2H, q, J=7.80 Hz, CH2CO), 2.05-2.45 (1H, d7, J=13.4 Hz, N(CHH)2), 2.5 (3H, m, CH3), 2.70-2.85 (2H, m, CH2Ph), 3.10 (1H, m, N(CHH)2), 3.25 (1H, m, N(CHH)2), 4.35 (1H, m, N(CHH)2), 4.45 (1H, m, CHNHCH3), 7.10-7.40 (5H, m, ArH), 8.8-9.2 (3H, bs, NH2+, OH), 10.32 (1H, s, NH).
MF: C19H29N3O3, MW: 347.452
1H NMR (DMSO-d6, 400 MHz): δ (ppm) −0.5-0.65 (2H, dq, J=12.1 Hz), 0.7-1.7 (7H, m), 1.95 (2H, q, J=7.80 Hz, CH2CO), 2.15-2.45 (1H, dt, J=13.3 Hz, N(CHH)2), 2.75-2.85 (2H, m, CH2Ph), 3.10 (1H, m, N(CHH)2), 3.45 (1H, m, N(CHH)2), 4.35 (1H, m, N(CHH)2), 4.50 (1H, m, CHNH2), 7.40-8.00 (7H, m, ArH), 8.2-8.5 (4H, bs, NH3+, OH), 10.28 (1H, d, J=13.00 Hz, NH).
MF: C22H29N3O3, MW: 383.48
1H NMR (DMSO-d6, 400 MHz): δ (ppm) −0.57-0.12 (1H, dq), 0.73-1.79 (8H, m), 1.86 (2H, m), 2.15-2.28 (1H, m), 2.37 (1H, t, J=12.5 Hz), 2.73 (2H, m), 3.18-3.36 (2H, m), 4.26 (1H, t, J=13.7 Hz, N(CHH)2), 4.73 (1H, s, CHNH2), 7.43 (2H, m, ArH), 7.61 (1H, s, ArH), 7.75-7.81 (1H, 2d, J=7.4 Hz, ArH), 8.02 (1H, d, J=7.7 Hz, ArH), 8.2-8.5 (3H, bs, NH3+), 8.69 (1H, brs, OH), 10.28 (1H, s, NH).
MF: C20H27N3O3S, MW: 389.51
1H NMR (DMSO-d6, 400 MHz): δ (ppm) −0.2-0.75 (1H, dq, J=12.10 Hz), 0.85-1.85 (8H, m), 1.95 (2H, q, J=7.9 Hz, CH2CO), 2.3 (3H, s, CH3), 2.25-2.45 (1H, m, N(CHH)2), 2.70-2.75 (1H, m, N(CHH)2), 2.75-2.85 (2H, m, CH2Ph), 3.40-3.50 (1H, m, N(CHH)2), 4.10-4.20 (1H, m, N(CHH)2), 4.50 (1H, m, CHNH2), 7.00-7.40 (4H, m, ArH), 8.1-8.4 (4H, bs, NH3+, OH), 10.25 (1H, d, J=13.0 Hz, NH).
MF C19H29N3O3, MW: 347.45
1H NMR (DMSO-d6, 400 MHz): δ (ppm) −0.20-0.75 (1H, 2q, J=12.1 Hz), 0.87-1.06 (2H, m), 1.12-1.22 (1H, m), 1.28-1.72 (5H, m), 1.95 (2H, 2t, J=7.3 Hz), 2.45 (1H, m, N(CHH)2), 2.90 (1H, t, J=13.5 Hz, N(CHH)2), 3.00-3.20 (2H, m, CH2Ph), 3.65-3.77 (1H, m, N(CHH)2), 4.37 (1H, d, N(CHH)2 J=12.8 Hz), 4.74 (1H, m, CHNH2), 7.41-7.48 (2H, m, ArH), 7.57-7.61 (2H, m, ArH), 7.68-7.77 (5H, m, ArH), 8.20 (3H, d, NH3+), 8.61 (1H, brs, OH), 10.29 (1H, d, J=9.9 Hz, NH).
MF C25H31N3O4, MW: 437.53
1H NMR (DMSO-d6, 400 MHz): δ (ppm) 0.0-0.80 (1H, dq, J=12.1 Hz), 0.85-1.85 (8H, m), 1.95 (2H, q, J=7.9 Hz, CH2CO), 2.35-2.45 (1H, m, N(CHH)2), 2.60-2.65 (1H, m, N(CHH)2), 2.75-2.85 (2H, m, CH2Ph), 3.40-3.50 (1H, m, N(CHH)2), 4.15 (1H, d, J=11.9 Hz, N(CHH)2), 4.55 (1H, m, CHNH2), 7.10-7.50 (4H, m, ArH), 8.10-8.35 (4H, bs, NH3+, OH), 10.20 (1H, d, J=13.0 Hz, NH).
MF C18H26FN3O3, MW: 351.42
MF C18H26FN3O3, MW: 351.42
MF C18H26FN3O3, MW: 351.42
1H NMR (DMSO-d6, 400 MHz): δ (ppm) 0.75-1.20 (4H, m), 1.40-1.80 (5H, m), 1.95 (2H, t, J=7.30 Hz, CH2CO), 2.50 (1H, m, CH2NH), 2.70 (1H, m, CH2NH), 2.85 (2H, m, CH2Ph), 3.90 (1H, t, J=12.3 Hz, CH2NH), 4.35 (1H, m, CH2NH), 4.40 (1H, d, J=10.9 Hz, CH2NH), 4.50 (1H, m, CHOH), 7.15-7.30 (5H, m, ArH), 8.65 (1H, bs, OH), 10.35 (1H, s, NH).
MF C18H26N2O4, MW: 334.41
1H NMR (DMSO-d6, 400 MHz): δ (ppm) 0.70-1.20 (4H, m), 1.40-1.80 (5H, m), 1.95 (2H, m, CH2CO), 2.55 (1H, t, J=12.5 Hz, CH2NH), 3.05 (1H, t, J=12.5 Hz, CH2NH), 3.60 (1H, m, CH2OH), 3.75 (1H, m, CH2OH), 4.05 (1H, d, J=12.3 Hz, CH2NH), 4.40 (1H, d, J=12.3 Hz, CH2NH), 4.90 (1H, m, CH2OH), 5.00 (1H, m, CHCH2OH), 7.40-7.50 (1H, m, ArH), 7.95 (1H, d, J=7.2 Hz, ArH), 8.05 (1H, d, J=7.2 Hz, ArH), 8.20-8.25 (1H, m, ArH), 8.65 (1H, bs, OH), 8.80 (1H, m, NHCH), 10.35 (1H, s, NH).
MF C21H27N3O5S, MW: 433.52
MF C21H27N3O5S, MW: 433.52
1H NMR (DMSO-d6, 400 MHz): δ (ppm) 0.70-1.20 (4H, m), 1.40-1.80 (7H, m, CH2NH and CH2CO), 2.50-2.60 (4H, m, CH2CH2NH), 2.65 (1H, m, CH2NH), 2.75 (3H, s, CH3), 2.85 (3H, s, CH3), 3.10 (1H, m, CH2NH), 3.90 (1H, m, CH2NH), 4.45 (1H, m, CH2NH), 4.60 (1H, m, CHN), 7.20-7.40 (5H, m, ArH), 9.80 (1H, m, +NH(CH3)2).
MF C21H33N3O3, MW: 375.50
1H NMR (DMSO-d6, 400 MHz): δ (ppm) 0.87-1.03 (2H, m), 1.10-1.21 (2H, m), 1.30-1.45 (1H, m) 1.45-1.56 (2H, quin, J=7.5 Hz), 1.56-1.67 (2H, m), 1.92 (2H, m, CH2CO), 2.66 (2H, m, N(CHH)2), 3.97 (2H, m, N(CHH)2), 4.23 (2H, s, PhCH2), 7.08 (1H, s, NCONH), 7.27 (1H, d, J=8.0 Hz, ArH), 7.42 (1H, d, J=8.0 Hz, ArH), 7.56 (1H, s, ArH), 8.69 (1H, bs, OH), 10.35 (1H, bs, NHOH).
MF C17H23ClN3O3, MW 388.29
1H NMR (DMSO-d6, 400 MHz): δ (ppm) 0.80-1.20 (4H, m), 1.40-1.80 (5H, m), 1.90-2.00 (4H, m, CH2CO and CH2Ph), 2.55-2.60 (2H, m, CH2CH2), 2.65 (1H, m, CH2NH), 2.95 (1H, q, J=14.8 Hz, CH2NH), 3.60 (1H, m, CH2NH), 4.20-4.30 (2H, m, CH2NH and CHNH), 7.10-7.40 (5H, m, ArH), 8.20-8.45 (2H, bs, OH and NHCH), 10.36 (1H, s, NH).
MF C19H29N3O3, MW: 347.45
1H NMR (DMSO-d6, 400 MHz): δ (ppm) 0.92 (2H, m), 1.07-1.22 (2H, m), 1.27-1.42 (1H, m) 1.49 (2H, m), 1.54-1.64 (2H, m), 1.91 (2H, t, J=7.2 Hz, CH2CO), 2.60 (2H, m, N(CHH)2), 3.93 (2H, m, N(CHH)2), 4.18 (2H, s, NHCH2), 6.09-6.16 (1H, m, FurH), 6.35 (1H, m, FurH), 6.90 (1H, m, NCONH), 7.52 (1H, m, FurH), 8.68 (1H, s, OH), 10.33 (1H, s, NHOH).
MF C15H23N3O4, MW 309.36
1H NMR (DMSO-d6, 400 MHz): δ (ppm) 0.70-1.20 (4H, m), 1.40-1.95 (11H, m, CH2CH2 and CH2CO and CH2N), 2.55 (1H, q, J=12.8 Hz, CH2NH), 2.80 (2H, m, CH2NH2), 3.00 (1H, t, J=12.8 Hz, CH2NH), 3.95 (1H, d, J=12.5 Hz, CH2NH), 4.40 (1H, t, J=12.5 Hz, CH2NH), 4.90 (1H, m, CHNH), 7.20-7.25 (2H, m, ArH), 7.65 (1H, m, NH+), 7.90-8.00 (2H, m, ArH), 8.20 (1H, s, ArH), 8.60 (1H, d, J=10.7 Hz, OH), 8.90-9.10 (1H, d, J=10.7 Hz, NHCH), 10.36 (1H, d, J=10.7 Hz, NH).
MF C23H32N4O4S, MW: 460.59
1H NMR (DMSO-d6, 400 MHz): δ (ppm) 0.78-1.18 (4H, m), 1.37-1.53 (3H, brs), 1.54-1.66 (2H, m), 1.91 (2H, dd, J=7.0 and 12.6 Hz), 2.52-2.68 (3H, m, N(CHH)2, and CHHCHN), 2.89 (1H, m, N(CHH)2), 3.02 (1H, m, CHHCHN), 3.09-3.15 (1H, m, CHHCHN), 3.64-3.70 (1H, m, N(CHH)2), 3.79 (1H, brs, CH2CHN), 4.34 (1H, d, J=12.7 Hz, N(CHH)2), 7.42-7.54 (3H, m, ArH), 7.76-7.92 (7H, m, +NH3, ArH), 8.68 (1H, brs, OH), 10.36 (1H, d, J=10.7 Hz, NH).
MF C23H31N3O3 MW 379.50
1H NMR (DMSO-d6, 400 MHz): δ (ppm) 0.67-0.90 (2H, m), 0.97-1.12 (2H, m), 1.35-1.65 (5H, m), 1.85-1.92 (2H, m), 2.54 (1H, m), 2.92 (1H, q), 2.99-3.10 (2H, m, COCH2CH), 3.77 (1H, d, J=13.9 Hz, N(CHH)2), 4.37 (1H, d, J=12.6 Hz, N(CHH)2), 4.78 (1H, s, CHNH2), 7.56-7.58 (2H, m, ArH), 7.62 (1H, d, ArH), 7.90-7.98 (3H, m, ArH), 8.00 (1H, s, ArH), 8.35 (3H, s, NH3+), 8.67 (1H, d, OH), 10.34 (1H, d, NH).
MF C22H29N3O3, MW 383.48
1H NMR (DMSO-d6, 400 MHz): δ (ppm) 0.70-1.20 (4H, m), 1.40-1.95 (9H, m, CH2NH and CHCH2CH2 and CH2CO), 2.55 (1H, m, CH2NH), 3.00 (1H, t, J=12.8 Hz, CH2NH), 3.40-3.50 (2H, m, CH2OH), 4.00 (1H, t, J=12.5 Hz, CH2NH), 4.35 (1H, d, J=12.5 Hz, CH2NH), 5.00 (1H, m, CHNH), 7.30-7.45 (2H, m, ArH), 7.85-8.00 (2H, m, ArH), 8.20 (1H, s, ArH), 8.60-8.65 (1H, m, OH), 8.90-9.10 (1H, m, NHCH), 10.36 (1H, m, NHOH).
MF C22H29N3O5S, MW: 460.59
1H NMR (DMSO-d6, 400 MHz): 6?(ppm) 0.65-0.93 (2H, m), 0.97-1.07 (2H, m), 1.35-1.61 (5H, m), 1.84-1.92 (2H, m), 2.54 (1H, s, N(CHH)2), 2.91 (1H, q, N(CHH)2), 2.96-3.15 (2H, m, CH2CH2CO), 3.77 (1H, d, J=13.2 Hz, N(CHH)2), 4.37 (1H, d, J=12.8 Hz, N(CHH)2), 4.78 (1H, s, CHNH2), 7.56-7.58 (2H, m, ArH), 7.90-7.98 (3H, m, ArH), 8.00 (1H, s), 8.38-8.45 (1H, d, OH), 10.34 (1H, s, NH).
MF C22H29NO3, MW 383.48
1H NMR (DMSO-d6, 400 MHz): δ (ppm) 0.76-0.95 (2H, m), 1.10-1.17 (2H, m), 1.39-1.52 (3H, m), 1.56-1.69 (2H, m), 1.90 (2H, q, J=7.1 Hz), 2.52 (1H, m, N(CHH)2), 2.88-2.99 (3H, m, CH2CO and N(CHH)2), 3.75 (1H, d, J=13.6 Hz, N(CHH)2), 4.37 (1H, d, J=12.8 Hz, N(CHH)2), 4.60 (1H, brs, CHNH2), 7.32-7.50 (5H, m, ArH), 8.28 (1H, d, OH), 10.33 (1H, s, NH).
MF C18H27NO3, MW 333.42
MF C22H29N3O5S, MW 460.59
1H NMR (DMSO-d6, 400 MHz): δ (ppm) 0.70-1.20 (4H, m), 1.40-1.80 (5H, m), 1.95 (2H, q, J=7.4 Hz, CH2CO), 2.55 (1H, t, J=11.9 Hz, CH2NH), 3.05 (1H, t, J=12.5 Hz, CH2NH), 3.55 (1H, m, CH2OH), 3.75 (1H, m, CH2OH), 4.10 (1H, d, J=11.9 Hz, CH2NH), 4.40 (1H, d, J=11.9 Hz, CH2NH), 5.00 (1H, m, CHCH2OH), 7.55 (1H, d, J=5.4 Hz, ArH), 7.65 (2H, m, ArH), 8.10 (1H, d, J=7.2 Hz, ArH), 8.45 (1H, d, J=5.4 Hz, ArH), 8.50-8.60 (1H, m, NHCH), 8.80 (1H, m, NHCH), 10.35 (1H, s, NH).
MF C21H27N3O5S, MW: 433.52
1H NMR (DMSO-d6, 400 MHz): δ (ppm) 0.75-1.25 (4H, m), 1.40-1.80 (5H, m), 1.85-1.95 (2H, dt, J=7.2 Hz, CH2CO), 2.55 (1H, m, CH2NH), 3.05 (1H, m, CH2NH), 3.06-3.20 (2H, m, CH2NH2), 3.80 (1H, m, CH2NH), 4.40 (1H, m, CH2NH), 5.15 (1H, m, CHCH2NH2), 7.20-7.30 (2H, m, ArH), 7.80-8.05 (3H, m, ArH and NH+), 7.65 (2H, m, ArH), 8.20 (1H, s, ArH), 8.50-8.60 (1H, m, NHCH), 9.25-9.40 (1H, d, J=8.8 Hz, NHCH), 10.35 (1H, m, NH).
MF C21H28N4O4S, MW: 432.54
1H NMR (DMSO-d6, 400 MHz): δ (ppm) 0.70-1.25 (4H, m), 1.40-1.80 (5H, m), 1.85-1.95 (2H, q, J=7.4 Hz, CH2CO), 2.55 (1H, t, J=11.6 Hz, CH2NH), 3.05 (1H, t, J=11.6 Hz, CH2NH), 3.30-3.40 (2H, m, CH2OH), 4.00 (1H, t, J=11.6 Hz, CH2NH), 4.35 (1H, d, J=11.6 Hz, CH2NH), 4.60 (1H, m, OH), 5.00 (1H, m, CHCH2OH), 7.00-7.20 (2H, m, ArH), 7.85-8.05 (2H, m, ArH), 8.22 (1H, m, ArH), 8.65 (1H, s, OH), 8.85-8.95 (1H, m, NHCH), 10.35 (1H, m, NH).
MF C22H29N3O5S, MW: 447.55
1H NMR (DMSO-d6, 400 MHz): δ (ppm) 0.70-1.30 (4H, m), 1.40-1.80 (5H, m), 1.85-1.95 (2H, m, CH2CO), 2.55 (1H, t, J=11.8 Hz, CH2NH), 3.05 (1H, t, J=11.8 Hz, CH2NH), 3.50-3.75 (2H, m, CH2OH), 4.10 (1H, d, J=11.6 Hz, CH2NH), 4.40 (1H, d, J=11.8 Hz, CH2NH), 4.85-5.00 (1H, dt, J=5.9 Hz, CHNH), 5.10 (1H, m, OH), 7.40-7.50 (2H, m, ArH), 8.04-8.10 (1H, d, J=7.9 Hz, ArH), 8.45-8.55 (2H, m, ArH), 8.60 (1H, d, J=7.9 Hz, NHCH), 8.75. 8-80 (1H, d, J=7.9 Hz, OH), 10.36 (1H, d, J=9.6 Hz, NH).
MF C21H27N3O5S, MW: 433.52
1H NMR (DMSO-d6, 400 MHz): δ (ppm) 0.65-1.30 (4H, m), 1.40-1.80 (5H, m), 1.85-1.95 (2H, m, CH2CO), 2.55 (1H, t, J=11.8 Hz, CH2NH), 3.05 (1H, t, J=11.8 Hz, CH2NH), 3.50-3.75 (2H, m, CH2OH), 4.10 (1H, d, J=11.6 Hz, CH2NH), 4.40 (1H, d, J=11.8 Hz, CH2NH), 5.10 (2H, m, OH and CHNH), 7.25-7.35 (2H, m, ArH), 7.60 (1H, d, J=8.40 Hz, ArH), 7.70 (1H, d, J=8.40 Hz, ArH), 7.80 (1H, d, J=8.40 Hz, ArH), 8.40-8.55 (2H, d, J=7.90 Hz, NHCH), 8.75. 8-80 (1H, m, OH), 10.36 (1H, s, NH).
MF C21H27N3O6, MW: 417.46
1H NMR (DMSO-d6, 400 MHz): δ (ppm) 0.54-0.83 (1H, 2q), 0.84-1.17 (4H, m), 1.28-1.66 (5H, m), 1.85-1.95 (2H, m), 2.45 (1H, m, N(CHH)2), 2.85 (1H, m, N(CHH)2), 3.40 (1H, m, CHHO), 3.59 (1H, m, CHHO), 3.81-3.91 (1H, m, N(CHH)2), 3.94 (2H, s, CH2Naf), 4.35 (1H, m, N(CHH)2), 4.79 (1H, m, CHNH3+), 4.89 (1H, t, J=6.0 Hz, OH), 7.38-7.54 (4H, m, ArH), 7.76-7.93 (2H, m, ArH), 8.02-8.13 (1H, m, ArH), 8.36-8.49 (1H, 2d, J=8.22 Hz, NHCH), 8.68 (1H, brs, OH), 10.36 (1H, brs, NH).
MF C24H31N3O5, MW 441.52
1H NMR (DMSO-d6, 400 MHz): δ (ppm) 0.75-1.30 (4H, m), 1.40-1.80 (5H, m), 1.85-1.95 (2H, m, CH2CO), 2.55 (1H, t, J=11.9 Hz, CH2NH), 3.05 (1H, t, J=11.9 Hz, CH2NH), 3.50-3.75 (2H, m, CH2OH), 4.10 (1H, d, J=11.9 Hz, CH2NH), 4.40 (1H, d, J=11.9 Hz, CH2NH), 4.95 (1H, m, OH), 5.10 (1H, m, CHNH), 7.00 (1H, t, J=7.9 Hz, ArH), 7.15 (1H, t, J=7.90 Hz, ArH), 7.25 (1H, d, J=7.90 Hz, ArH), 7.40 (1H, d, J=7.9 Hz, ArH), 7.6 (1H, d, J=7.9 Hz, ArH), 8.04-8.10 (1H, d, J=7.9 Hz, ArH), 8.40-8.55 (1H, d, J=8.2 Hz, NHCH), 8.65 (1H, d, J=6.8 Hz, OH), 10.36 (1H, d, J=10.25 Hz, NH), 11.60 (1H, m, NHInd).
MF C21H28N3O5, MW: 416.47
1H NMR (DMSO-d6, 400 MHz): δ (ppm) 0.80-1.30 (4H, m), 1.45-1.80 (5H, m), 1.85-1.95 (2H, m, CH2CO), 2.60 (1H, q, J=11.7 Hz, CH2NH), 3.05 (1H, m, CH2NH), 3.40 (2H, s, CH2OH), 4.10 (1H, d, J=11.7 Hz, CH2NH), 4.40 (1H, d, J=11.7 Hz, CH2NH), 5.05 (1H, q, J=5.54 Hz, CHNH), 7.70 (1H, t, J=7.8 Hz, ArH), 7.90 (1H, t, J=7.8 Hz, ArH), 8.10-8.40 (3H, m, ArH), 8.60 (1H, d, J=8.6 Hz, ArH), 8.80-8.90 (1H, m, NHCH), 10.36 (1H, d, J=7.8 Hz, NHOH).
MF C22H28N4O5, MW: 428.48
1H NMR (DMSO-d6, 400 MHz): δ (ppm) 0.75-1.30 (4H, m), 1.45-1.80 (5H, m), 1.85-1.95 (2H, q, J=7.6 Hz CH2CO), 2.65 (1H, m, CH2NH), 3.05 (1H, t, J=12.0 Hz, CH2NH), 3.55-3.65 (2H, m, CH2OH), 4.10 (1H, d, J=12.0 Hz, CH2NH), 4.40 (1H, d, J=12.0 Hz, CH2NH), 5.05-5.10 (1H, m, CHNH), 7.40 (1H, t, J=7.8 Hz, ArH), 7.75 (1H, t, J=7.8 Hz, ArH), 8.05 (2H, d, J=6.6 Hz, ArH), 8.58 (1H, d, J=5.6 Hz, ArH), 9.15 (1H, d, J=8.4 Hz, ArH), 8.85-8.95 (1H, m, NHCH), 10.35 (1H, m, NHOH).
MF C22H28N4O5, MW 428.48
1H NMR (DMSO-d6, 400 MHz): δ (ppm) 0.75-1.30 (4H, m), 1.45-1.80 (5H, m), 1.80-1.95 (2H, q, J=7.8 Hz CH2CO), 2.65 (1H, q, J=11.9 Hz, CH2NH), 3.05 (1H, m, CH2NH), 3.55-3.65 (2H, m, CH2OH), 4.10 (1H, d, J=12.6 Hz, CH2NH), 4.40 (1H, d, J=12.6 Hz, CH2NH), 5.05-5.10 (1H, m, CHNH), 7.80-7-92 (2H, dt, J=7.9 Hz, ArH), 8.22 (1H, d, J=8.2 Hz, ArH), 8.28 (1H, d, J=8.2 Hz, ArH), 8.58 (1H, d, J=4.6 Hz, ArH), 8.85-8.95 (1H, m, NHCH), 9.40 (1H, s, ArH), 10.35 (1H, m, NHOH).
MF C22H28N4O5, MW 428.48
1H NMR (DMSO-d6, 400 MHz): δ (ppm) 0.80-1.30 (4H, m), 1.45-1.80 (5H, m), 1.80-1.95 (2H, dt, J=7.2 Hz, CH2CO), 2.65 (1H, m, CH2NH), 3.05 (1H, m, CH2NH), 3.00-3.20 (2H, m, CH2NH2), 4.10 (1H, m, CH2NH), 4.40 (1H, m, CH2NH), 5.05-5.10 (1H, m, CHNH), 7.40-7.50 (2H, m, ArH), 7.80-8.10 (3H, m, NH3+, ArH), 8.20 (1H, s, ArH), 8.60 (1H, bs, OH), 9.30-9.40 (1H, m, NHCH), 10.35 (1H, m, NHOH).
MF C22H28N4O5, MW: 432.54
1H NMR (DMSO-d6, 400 MHz): δ (ppm) 0.84-1.02 (2H, m), 1.10-1.26 (2H, m), 1.29-1.43 (1H, m) 1.43-1.70 (4H, m), 1.92 (2H, t, J=7.2 Hz, CH2CO), 2.63 (2H, m, N(CHH)2), 3.94 (2H, m, N(CHH)2), 4.21 (2H, s, PhCH2), 7.02 (1H, s, NCONH), 7.18-7.42 (3H, m, ArH), 8.67 (1H, bs, OH), 10.33 (1H, s, NHOH).
MF C17H23ClFN3O3, MW 371.83
1H NMR (DMSO-d6, 400 MHz): δ (ppm) 1.05 (2H, dq, J=3.5 and 12.6 Hz), 1.14-1.28 (2H, m), 1.38-1.48 (1H, m) 1.53 (2H, quin, J=7.4 Hz), 1.62-1.73 (2H, m), 1.95 (2H, t, J=7.2 Hz, CH2CO), 2.25 (3H, s, CH3), 2.77 (2H, m, N(CHH)2), 4.10 (2H, m, N(CHH)2), 6.76-6.93 (2H, m, ArH), 7.23 (1H, m, ArH), 8.29 (3H, bs, NH2+) 8.71 (1H, bs, OH), 10.36 (1H, s, NHOH).
MF C17H26N4O3, MW 334.41
1H NMR (DMSO-d6, 400 MHz): δ (ppm) 1.02 (2H, dq, J=3.5 and 12.6 Hz), 1.14-1.27 (2H, m), 1.33-1.48 (1H, m) 1.53 (2H, m), 1.59-1.70 (2H, m), 1.95 (2H, t, J=7.2 Hz, CH2CO), 2.72 (2H, m, N(CHH)2), 3.78 (3H, s, OCH3), 4.06 (2H, m, N(CHH)2), 6.79 (1H, m, ArH), 6.82-6.88 (1H, m, ArH), 7.14. 7.23 (1H, m, ArH), 7.68 (1H, s, NCONH), 8.70 (1H, bs, OH), 10.36 (1H, s, NHOH).
MF C17H24FN3O4, MW 353.39
1H NMR (DMSO-d6, 400 MHz): δ (ppm) 1.02 (2H, dq, J=3.8 and 12.6 Hz), 1.13-1.28 (2H, m), 1.34-1.47 (1H, m) 1.53 (2H, m), 1.60-1.72 (2H, m), 1.94 (2H, t, J=7.2 Hz, CH2CO), 2.25 (3H, s, CH3), 2.74 (2H, m, N(CHH)2), 4.06 (2H, m, N(CHH)2), 6.85-6.92 (1H, m, ArH), 6.98-7.08 (1H, m, ArH), 7.18-7.25 (1H, m, ArH), 8.14 (1H, s, NCONH), 8.69 (1H, s, OH), 10.36 (1H, s, NHOH).
MF C17H24FN3O3, MW 337.39
1H NMR (DMSO-d6, 400 MHz): δ (ppm) 0.93-1.14 (2H, m), 1.14-1.32 (2H, m), 1.38-1.60 (3H, m) 1.60-1.75 (2H, m), 1.95 (2H, t, J=7.2 Hz, CH2CO), 2.78 (2H, m, N(CHH)2), 4.07 (2H, m, N(CHH)2), 7.13-7.42 (3H, m, ArH), 8.21 (1H, s, NCONH), 8.70 (1H, bs, OH), 10.36 (1H, s, NHOH).
MF C16H21ClFN3O3, MW 357.81
1H NMR (DMSO-d6, 400 MHz): 6 ?(ppm) 0.76-0.92 (2H, m), 1.07-1.28 (2H, m), 1.39-1.64 (5H, m), 1.92 (2H, q, J=7.1 Hz), 2.52 (1H, s, N(CHH)2), 2.86-3.01 (3H, m, CH2CO, N(CHH)2), 3.75 (1H, d, J=13.1 Hz, N(CHH)2), 4.37 (1H, d, J=12.6 Hz, N(CHH)2), 4.60 (1H, s, CHNH2), 7.36-7.49 (5H, m, ArH), 8.23 (3H, bs, NH3+), 8.67 (1H, s, OH), 10.34 (1H, s, NH).
MF C18H27NO3, MW 333.42
1H NMR (DMSO-d6, 400 MHz): δ (ppm) 0.89-1.03 (2H, m), 1.16 (2H, m), 1.45-1.53 (2H, m), 1.66-1.95 (5H, m), 2.59 (2H, m, N(CHH)2), 2.68 (2H, t, J=8.0 Hz), 2.83 (1H, dd), 2.97 (1H, t, J=12.3 Hz, CH2CO), 3.82 (1H, d, J=13.6 Hz, N(CHH)2), 4.41 (1H, bs, CHNH2), 7.21-7.32 (5H, m, ArH), 7.79 (3H, bs, NH3+), 8.70 (1H, s, OH), 10.36 (1H, s, NH).
MF C20H31NO3, MW 361.48
1H NMR (CDCl3-d1, 400 MHz): δ (ppm) 1.37-1.58 (4H, m), 1.65-1.81 (1H, m), 1.81-2.09 (4H, m), 2.39 (2H, m, CH2CO), 3.18 (2H, m, N(CHH)2), 4.41-4.58 (2H, m, N(CHH)2), 7.60-7.72 (2H, m, ArH), 7.72-7.82 (1H, m, ArH), 8.42 (1H, d, J=8.0 Hz, ArH), 8.74 (1H, d, J=8.0 Hz, ArH), 9.02 (1H, s, ArH), 9.62 (1H, s, NCONH).
MF C19H24N4O3, MW 356.42
1H NMR (DMSO-d6, 400 MHz): 6?(ppm) 0.85-0.95 (2H, m), 1.04-1.11 (2H, m), 1.17-1.25 (1H, brs), 1.37-1.47 (2H, m), 1.57-1.65 (2H, d, J=12.4 Hz), 1.88 (2H, t, J=7.2 Hz), 2.61 (2H, t, J=11.8 Hz), 3.57 (2H, d, 12.1 Hz), 7.01-7.04 (1H, t, ArH, J=7.3 Hz), 7.16-7.18 (2H, d, ArH, J=8.3 Hz), 7.26-7.30 (2H, t, ArH, J=7.7 Hz), 8.70 (1H, s, OH), 9.85 (1H, s, NHPh), 10.30 (1H, s, NH).
MF C15H23N3O4S, MW 341.43
1H NMR (DMSO-d6, 400 MHz): 6?(ppm) 1.05-1.21 (2H, m), 1.37 (2H, m), 1.69 (3H, m), 1.87 (2H, brs), 2.13 (2H, s), 2.45 (2H, m, CH2CO, N(CHH)2), 3.00-3.20 (3H, m, CH2Ph, CH2CO), 3.86 (2H, s, NCH), 4.59 (1H, d, J=12.7 Hz, N(CHH)2), 7.47-7.58 (5H, m, ArH), 8.04-8.06 (3H, bs, NH3+), 8.86 (1H, s, OH), 10.56 (1H, s, NH).
MF C19H29N3O3, MW 347.45
1H NMR (DMSO-d6, 400 MHz): δ (ppm) 0.93-1.13 (2H, m), 1.13-1.28 (2H, m), 1.33-1.47 (1H, m), 1.52 (2H, m), 1.61-1.75 (2H, m), 1.94 (2H, t, J=7.2 Hz, CH2CO), 2.75 (2H, m, N(CHH)2), 4.12 (2H, m, N(CHH)2), 7.30 (1H, m, ArH), 7.38-7.46 (2H, m, ArH), 7.50-7.59 (4H, m, ArH), 7.62 (2H, d, J=7.6 Hz, ArH), 8.55 (1H, s, NCONH), 8.70 (1H, bs, OH), 10.34 (1H, s, NHOH).
MF C22H27N3O3, MW 381.47
1H NMR (DMSO-d6, 400 MHz): δ (ppm) 0.83-1.00 (2H, m), 1.08-1.22 (2H, m), 1.27-1.41 (1H, m), 1.49 (2H, m), 1.54-1.65 (2H, m), 1.92 (2H, t, J=7.2 Hz, CH2CO), 2.61 (2H, m, N(CHH)2), 3.94 (2H, m, N(CHH)2), 4.10 (2H, s, OCH2O), 5.96 (2H, s, CH2Ph), 6.66-6.73 (1H, m, ArH), 6.77-6.85 (2H, m, ArH), 6.93 (1H, m, NCONH), 10.33 (1H, s, NHOH).
MF C18H25N3O5, MW 363.41
1H NMR (DMSO-d6, 400 MHz): δ (ppm) 0.93-1.07 (2H, m), 1.13-1.24 (2H, m), 1.32-1.46 (1H, m), 1.52 (2H, m), 1.59-1.72 (2H, m), 1.93 (2H, t, J=7.2 Hz, CH2CO), 2.73 (2H, m, N(CHH)2), 4.09 (2H, m, N(CHH)2), 6.92 (4H, m, ArH), 7.07 (1H, m), 7.34 (2H, m, ArH), 7.46 (2H, d, J=8.4 Hz, ArH), 8.46 (1H, s, NCONH), 8.68 (1H, s, OH), 10.34 (1H, s, NHOH).
MF C22H27N3O4, MW 397.47
1H NMR (DMSO-d6, 400 MHz): δ (ppm) 0.90-1.04 (2H, m), 0.95 (3H, t, J=7.2 Hz, CH3), 1.13-1.26 (2H, m), 1.33-1.45 (1H, m), 1.51 (2H, quin, J=7.4 Hz), 1.59-1.75 (4H, m), 1.93 (2H, t, J=7.2 Hz, CH2CO), 2.70 (2H, m, N(CHH)2), 3.84 (2H, t, J=6.4 Hz, PhOCH2), 4.07 (2H, m, N(CHH)2), 6.78 (2H, d, J=8.8 Hz, ArH), 7.30 (2H, d, J=8.8 Hz, ArH), 8.25 (1H, s, NCONH), 8.68 (1H, bs, OH), 10.34 (1H, s, NHOH).
MF C19H29N3O4, MW 397.47
1H NMR (DMSO-d6, 400 MHz): δ (ppm) 0.90-1.06 (2H, m), 1.12-1.20 (2H, m), 1.22 (6H, d, J=6.0 Hz, CH(CH3)2), 1.32-1.45 (1H, m), 1.51 (2H, m), 1.59-1.69 (2H, m), 1.93 (2H, t, J=7.2 Hz, CH2CO), 2.70 (2H, m, N(CHH)2), 4.07 (2H, m, N(CHH)2), 4.48 (1H, hept, J=6.0 Hz, CH(CH3)2), 6.77 (2H, d, J=8.4 Hz, ArH), 7.29 (2H, d, J=8.4 Hz, ArH), 8.25 (1H, s, NCONH), 8.39-8.93 (1H, bs, OH), 10.34 (1H, s, NHOH).
MF C20H29N3O4, MW 363.45
1H NMR (DMSO-d6, 400 MHz): δ (ppm) 0.83-0.99 (2H, m), 1.09-1.20 (2H, m), 1.26-1.40 (1H, m), 1.33 (3H, d, J=6.8 Hz, CH3), 1.43-1.53 (2H, m), 1.54-1.64 (2H, m), 1.92 (2H, t, J=7.2 Hz, CH2CO), 2.59 (2H, m, N(CHH)2), 3.98 (2H, m, N(CHH)2), 4.81 (1H, m, CHNH), 6.69 (1H, d, J=8.0 Hz, ArH), 7.14-7.21 (1H, m, CHNH), 7.26-7.32 (4H, m, ArH), 8.68 (1H, s, OH), 10.33 (1H, s, NHOH).
MF C18H27N3O3, MW 333.42
MF C18H27NO3, MW 333.42
MF C22H29N3O3, MW 383.48
1H NMR (DMSO-d6, 400 MHz): δ (ppm) 1.01-1.15 (2H, m), 1.16-1.25 (2H, m), 1.40-1.60 (3H, m), 1.66-1.78 (2H, m), 1.94 (2H, t, J=7.2 Hz, CH2CO), 2.88 (2H, m, N(CHH)2), 4.20 (2H, m, N(CHH)2), 7.56 (1H, m, ArH), 7.75-7.87 (2H, m, ArH), 7.75-7.87 (2H, m, ArH), 7.98 (2H, d, J=7.6 Hz, ArH), 8.48 (1H, m, ArH), 10.34 (1H, s, NHOH).
MF C19H24N4O3, MW 356.42
1H NMR (DMSO-d6, 400 MHz): δ (ppm) 0.70-1.30 (4H, m), 1.45-1.80 (5H, m), 1.80-1.95 (2H, m, CH2CO), 2.65 (2H, t, J=6.6 Hz, COCH2CH), 2.70-2.85 (1H, q, J=6.6 Hz, CH2NH), 3.00-3.20 (2H, m, CH2Ph), 3.30-3.80 (3H, m, CH2NH, and CHNH), 4.35 (1H, m, CHNH), 7.40-7.55 (3H, m, ArH), 7.80 (1H, s, ArH), 7.85-7.95 (3H, m, ArH), 8.00-8.20 (1H, m, NH3+), 8.36 (1H, s, OH), 10.35 (1H, s, NHOH).
MF C23H31N3O5, MW 397.51
1H NMR (DMSO-d6, 400 MHz): δ (ppm) 0.99 (2H, m), 1.13-1.24 (2H, m), 1.21 (6H, t, J=7.3, N(CH2CH3)2), 1.35-1.46 (1H, m), 1.48-1.57 (2H, m), 1.61-1.70 (2H, m), 1.93 (2H, t, J=7.3 Hz, CH2CO), 2.72 (2H, m, N(CHH)2), 2.82-2.91 (2H, m, PhCH2), 3.16-3.27 (6H, m, CH2N(CH2 CH3)2), 4.08 (2H, m, N(CHH)2), 7.15 (2H, d, J=8.6 Hz, ArH), 7.41 (2H, d, J=8.6 Hz, ArH), 8.41 (1H, m, NHCON), 9.11 (1H, bs, OH), 10.32 (1H, s, NHOH).
MF C22H36N4O3, MW 404.55
1H NMR (DMSO-d6, 400 MHz): δ (ppm) 0.82-0.94 (2H, m), 1.12-1.17 (2H, m), 1.39-1.69 (5H, m), 1.92 (2H, m), 2.54-2.75 (3H, m, COCH2CH, N(CHH)2), 2.87-2.95 (1H, m, N(CHH)2), 3.16 (2H, m, NCHCHH), 3.66-3.77 (2H, m, NCHCH2, N(CHH)2), 4.38 (1H, d, J=13.6 Hz, N(CHH)2), 7.40-7.47 (2H, m, ArH), 7.61 (1H, s, ArH), 7.91-8.04 (3H, m, ArH and NH+), 8.66 (1H, brs, OH), 10.31 (1H, s, NHOH).
MF C21H29N3O5S, MW: 403.54
MF C21H29N3O5S, MW: 403.54
1H NMR (DMSO-d6, 400 MHz): δ (ppm) 0.80-1.30 (4H, m), 1.45-1.80 (5H, m), 1.85-1.95 (2H, dt, J=7.23 Hz, CH2CO), 2.50-2.70 (1H, m, CH2NH), 2.90-3.10 (1H, q, J=12.0 Hz, CH2NH), 3.00-3.20 (2H, m, CH2Ph), 3.80 (1H, t, J=12.0 Hz, CH2NH), 4.35 (1H, d, J=11.7 Hz, CH2NH), 5.30 (1H, m, CH2CHNH), 7.40-7.50 (2H, m, ArH), 7.95 (1H, t, J=8.1 Hz, ArH), 8.05 (1H, t, J=7.6 Hz, ArH), 8.20 (1H, s, ArH), 8.60 (1H, bs, OH), 9.35-9.45 (1H, d, J=8.8 Hz, NHCH), 10.35 (1H, m, NHOH).
MF C23H32N4O4S, MW: 460.59
1H NMR (DMSO-d6, 400 MHz): δ (ppm) 0.63-1.12 (4H, m), 1.44 (3H, m), 1.60 (2H, m), 1.89-1.91 (2H, td, J=7.3 and 14.6 Hz), 2.64 (3H, s, CH3), 2.79 (3H, s, CH3), 2.98 (1H, q, J=10.7 Hz), 3.41 (3H, m, NCHCH2 and N(CHH)2), 3.96 (1H, d, J=12.8 Hz, N(CHH)2), 4.28 (1H, d, J=11.6 Hz, N(CHH)2), 5.01 (1H, s, NCHCH2), 7.59-8.12 (7H, m, ArH), 9.72 (1H, s, OH), 10.29 (1H, s, NH).
MF C24H33N3O3, MW 411.54
MF C22H27N3O3, MW 381.46
1H NMR (DMSO-d6, 400 MHz): δ (ppm) 1.03 (2H, dq, J=3.2 and 12.0 Hz), 1.11-1.28 (2H, m), 1.36-1.48 (1H, m), 1.53 (2H, quin, J=7.4 Hz), 1.62-1.72 (2H, m), 1.94 (2H, t, J=7.3 Hz, CH2CO), 2.77 (2H, m, N(CHH)2), 4.13 (2H, m, N(CHH)2), 7.41-7.53 (2H, m, ArH), 7.65 (2H, d, J=8.0 Hz, ArH), 7.95 (2H, d, J=8.0 Hz, ArH), 8.00-8.13 (2H, m, ArH), 8.67 (1H, m, NHCON), 8.72 (1H, bs, OH), 10.32 (1H, s, NHOH).
MF C21H26N4O3, MW 382.46
1H NMR (DMSO-d6, 400 MHz): δ (ppm) 1.02 (2H, dq, J=3.0 and 12.4 Hz), 1.13-1.24 (2H, m), 1.34-1.46 (1H, m), 1.52 (2H, quin, J=7.4 Hz), 1.62-1.73 (2H, m), 1.94 (2H, t, J=7.3 Hz, CH2CO), 2.75 (2H, m, N(CHH)2), 4.11 (2H, m, N(CHH)2), 7.51 (1H, s, OxazH), 7.56-7.60 (4H, m, ArH), 8.35 (1H, s, OxazH), 8.62 (1H, m, NHCON), 8.65 (1H, s, OH), 10.32 (1H, s, NHOH).
MF C19H24N4O4, MW 372.42
MF C21H26N4O3, MW 382.45
MF C23H31N3O3, MW 397.51
1H NMR (DMSO-d6, 400 MHz): δ (ppm) 0.80-0.95 (2H, m), 1.09-1.20 (2H, m), 1.39-1.70 (5H, m), 1.92 (2H, q, J=7.4 Hz), 2.62-2.67 (2H, m, CH2CHNH2CH2), 2.89 (1H, q, J=12.1 Hz), 3.37 (2H, m, CH2CHNH2CH2), 3.67 (1H, d, J=13.9 Hz, N(CHH)2), 3.77 (1H, s, CH2CHNH2CH2), 4.35 (1H, d, J=14.2 Hz, N(CHH)2, 7.42-7.63 (4H, m, ArH), 7.87-7.98 (3H, m, ArH and NH+), 8.21 (1H, d, J=8.3 Hz, ArH), 8.60 (1H, bs, OH), 10.32 (1H, s, NHOH).
MF C23H31N3O3, MW 397.51
1H NMR (DMSO-d6, 400 MHz): δ (ppm) 0.96 (2H, m), 1.11-1.21 (2H, m), 1.31-1.45 (1H, m) 1.50 (2H, quint, J=7.6 Hz), 1.56-1.65 (2H, m), 1.92 (2H, t, J=7.6 Hz, CH2CO), 2.65 (2H, m, N(CHH)2), 3.98 (2H, m, N(CHH)2), 4.36 (2H, m, PhCH2), 7.04 (1H, bs, NCONH), 7.29 (1H, s, ThiazH), 7.33-7.53 (3H, m, ArH), 7.87-7.95 (2H, m, ArH), 10.30 (1H, s, NHOH).
MF C20H26N4O3S, MW 402.51
1H NMR (DMSO-d6, 400 MHz): δ (ppm) 0.93 (2H, dq, J=3.6 and 12.4 Hz), 1.10-1.20 (2H, m), 1.30-1.43 (1H, m) 1.50 (2H, quint, J=7.6 Hz), 1.54-1.63 (2H, m), 1.92 (2H, t, J=7.6 Hz, CH2CO), 2.63 (2H, m, N(CHH)2), 3.97 (2H, m, N(CHH)2), 4.46 (2H, m, PhCH2), 6.96 (1H, bs, NCONH), 7.33-7.43 (3H, m, ArH), 7.93 (2H, dd, J=1.6 and 12.0 Hz, ArH), 10.31 (1H, s, NHOH).
MF C19H25N3O3S, MW 375.49
MF C22H29N3O3, MW 383.48
1H NMR (DMSO-d6, 400 MHz): δ (ppm) 0.61-0.91 (2H, m), 1.12 (1H, m), 1.34-1.65 (6H, m), 1.92 (2H, q, J=7.4 Hz), 2.51 (1H, m, N(CHH)2), 2.86 (1H, q, J=12.2 Hz, N(CHH)2), 2.99-3.16 (2H, m, CH2CH2CO), 3.70 (1H, brs, N(CHH)2), 4.36 (1H, brs, N(CHH)2), 5.48 (1H, s, CHNH2), 7.54-7.74 (4H, m, ArH), 8.00 (2H, t, J=9.4 Hz, ArH), 8.13 (1H, d, J=8.4 Hz, ArH), 8.45-8.50 (2H, bs, OH, NH+), 10.32 (1H, s, NHOH).
MF C22H29N3O3, MW 383.48
1H NMR (DMSO-d6, 400 MHz): δ (ppm) 0.97-1.14 (2H, m), 1.14-1.27 (2H, m), 1.38-1.50 (1H, m) 1.53 (2H, quin, J=7.4 Hz), 1.63-1.73 (2H, m), 1.94 (2H, t, J=7.6 Hz, CH2CO), 2.82 (2H, m, N(CHH)2), 3.82 (3H, s, OCH3), 4.13 (2H, m, N(CHH)2), 7.42 (1H, t, J=7.2 Hz, ArH), 7.51 (1H, t, J=7.2 Hz, ArH), 7.61 (1H, d, J=8.8 Hz, ArH), 7.75 (1H, d, J=8.8 Hz, ArH), 7.87 (1H, d, J=8.0 Hz, ArH), 7.99 (1H, d, J=8.0 Hz, ArH), 8.05 (1H, s, NCONH), 8.66 (1H, s, OH), 10.32 (1H, s, NHOH).
MF C21H27N3O4, MW 385.46
1H NMR (DMSO-d6, 400 MHz): δ (ppm) 0.99-1.12 (2H, m), 1.14-1.25 (2H, m), 1.37-1.48 (1H, m) 1.53 (2H, quin, J=7.6 Hz), 1.65-1.74 (2H, m), 1.94 (2H, t, J=7.6 Hz, CH2CO), 2.81 (2H, m, N(CHH)2), 3.96 (3H, s, OCH3), 4.05 (2H, m, N(CHH)2), 7.25-7.36 (3H, m, ArH), 7.66-7.79 (2H, m, ArH), 8.25-8.29 (1H, m, ArH), 8.66 (1H, s, OH), 10.32 (1H, s, NHOH).
MF C21H27N3O4, MW 385.46
1H NMR (DMSO-d6, 400 MHz): δ (ppm) 0.91 (2H, dq, J=3.6 and 11.6 Hz), 1.08-1.20 (2H, m), 1.27-1.41 (1H, m) 1.49 (2H, quin, J=7.6 Hz), 1.53-1.62 (2H, m), 1.91 (2H, t, J=7.2 Hz, CH2CO), 2.37 (3H, s, CH3), 2.60 (2H, m, N(CHH)2), 3.94 (2H, m, N(CHH)2), 4.09 (2H, m, PhCH2), 6.87 (1H, t, J=5.6 Hz, NCONH), 7.43-7.55 (3H, m, ArH), 7.85-7.95 (2H, m, ArH), 8.65 (1H, bs, OH), 10.30 (1H, s, NHOH).
MF C21H28NO4, MW 400.47
1H NMR (DMSO-d6, 400 MHz): δ (ppm) 0.84-0.99 (2H, m), 1.11-1.21 (2H, m), 1.28-1.41 (1H, m) 1.50 (2H, quin, J=7.6 Hz), 1.54-1.62 (2H, m), 1.92 (2H, t, J=7.6 Hz, CH2CO), 2.60 (2H, m, N(CHH)2), 2.80 (2H, J=7.6 Hz, NHCH2CH2), 3.26 (2H, J=7.6 Hz, NHCH2CH2), 3.92 (2H, m, N(CHH)2), 6.96 (1H, t, J=7.4 Hz, ArH), 7.05 (1H, t, J=7.4 Hz, ArH), 7.11 (1H, s, IndH), 7.32 (1H, d, J=8.0 Hz, ArH), 7.54 (1H, d, J=8.0 Hz, ArH), 10.31 (1H, s, NHOH), 10.75 (1H, s, IndNH).
MF C20H28N4O3, MW 372.46
1H NMR (DMSO-d6, 400 MHz): δ (ppm) 0.75-1.30 (4H, m), 1.45-1.80 (5H, m), 1.95 (2H, t, J=7.0 Hz, CH2CO), 2.55 (1H, t, J=11.5 Hz, CH2NH), 2.70 (2H, t, J=6.7 Hz, CH2CO), 2.95 (1H, t, J=11.5 Hz, CH2NH), 3.10 (2H, t, J=6.7 Hz, CH2NH), 3.70 (1H, d, J=11.5 Hz, CH2NH), 4.18 (2H, s, CH2Ph), 4.35 (1H, d, J=11.5 Hz, CH2NH), 7.40-7.55 (5H, m, ArH), 8.60 (1H, s, NH+), 8.65 (1H, bs, OH), 10.35 (1H, s, NHOH).
MF C19H29N3O3, MW: 347.452
1H NMR (DMSO-d6, 400 MHz): δ (ppm) 1.02 (2H, dq, J=3.4 and 12.3 Hz), 1.11-1.29 (2H, m), 1.36-1.48 (1H, m), 1.48-1.59 (2H, m), 1.62-1.73 (2H, m), 1.94 (2H, t, J=7.3 Hz, CH2CO), 2.75 (2H, m, N(CHH)2), 4.12 (2H, m, N(CHH)2), 7.07-7015 (1H, m, ArH), 7.41-7051 (4H, m, ArH), 7.54-7.62 (3H, m, ArH), 8.57 (1H, m, NHCON), 8.67 (1H, bs, OH), 10.32 (1H, s, NHOH).
MF C22H26FN3O3, MW 399.46
1H NMR (DMSO-d6, 400 MHz): δ (ppm) 1.02 (2H, m), 1.13-1.29 (2H, m), 1.37-1.47 (1H, m), 1.47-1.60 (2H, m), 1.63-1.73 (2H, m), 1.94 (2H, t, J=7.3 Hz, CH2CO), 2.75 (2H, m, N(CHH)2), 4.11 (2H, m, N(CHH)2), 7.24 (2H, m, ArH), 7.53 (4H, m, ArH), 7.65 (2H, m, ArH), 8.53 (1H, m, NHCON), 8.65 (1H, bs, OH), 10.32 (1H, s, NHOH).
MF C22H26FN3O3, MW 399.46
MF C18H26ClN3O3, MW 367.87
1H NMR (DMSO-d6, 400 MHz): δ (ppm) 0.84-0.96 (2H, m), 1.13 (2H, m), 1.47 (3H, brs), 1.64 (2H, m), 1.92 (2H, brs), 2.54 (1H, m, N(CHH)2), 2.84-3.07 (3H, m, CH2CO, N(CHH)2), 3.76 (1H, d, J=13.1 Hz, N(CHH)2), 4.37 (1H, d, J=12.8 Hz, N(CHH)2), 4.62 (1H, s, CHNH2), 7.45 (3H, s, ArH), 7.61 (1H, s, ArH), 8.33 (1H, s, OH), 10.30 (1H, s, NH).
MF C18H26ClN3O3, MW 367.87
1H NMR (DMSO-d6, 400 MHz): δ (ppm) 1.02 (2H, dq, J=3.6 and 12.5 Hz), 1.15-1.26 (2H, m), 1.36-1.47 (1H, m), 1.47-1.58 (2H, m), 1.61-1.72 (2H, m), 1.94 (2H, t, J=7.3 Hz, CH2CO), 2.74 (2H, m, N(CHH)2), 3.77 (3H, s, OCH3), 4.11 (2H, m, N(CHH)2), 6.98 (2H, d, J=8.8 Hz, ArH), 7.44-7.59 (6H, m, ArH), 8.48 (1H, m, NHCON), 8.54 (1H, bs, OH), 10.32 (1H, s, NHOH).
MF C23H29N3O4, MW 411.49
1H NMR (DMSO-d6, 400 MHz): δ (ppm) 0.91 (2H, dq, J=3.2 and 12.4 Hz), 1.09-1.19 (2H, m), 1.27-1.40 (1H, m) 1.49 (2H, quint, J=7.2 Hz), 1.53-1.62 (2H, m), 1.76 (2H, quint, J=7.2 Hz, NCH2CH2CH2), 1.91 (2H, t, J=7.2 Hz, CH2CO), 2.57 (2H, t, J=11.6 Hz, NCH2CH2CH2), 2.65 (2H, m, N(CHH)2), 3.07 (2H, t, J=6.8 Hz, NCH2CH2CH2), 3.91 (2H, m, N(CHH)2), 6.39 (1H, s, NCONH), 6.95 (1H, t, J=7.6 Hz, ArH), 7.05 (1H, t, J=7.6 Hz, ArH), 7.11 (1H, s, ArH), 7.31 (1H, d, J=8.0 Hz, ArH), 7.47 (1H, d, J=8.0 Hz, ArH), 10.30 (1H, s, NHOH), 10.72 (1H, bs, IndNH).
MF C21H30N4O3, MW 386.49
MF C18H26ClN3O3, MW 367.87
1H NMR (DMSO-d6, 400 MHz): δ (ppm) 0.99 (2H, dq, J=3.6 and 12.9 Hz), 1.11-1.26 (2H, m), 1.46-1.54 (3H, m), 1.60-1.70 (2H, m), 1.93 (2H, t, J=7.3 Hz, CH2CO), 2.91 (2H, m, N(CHH)2), 3.81 (3H, s, OCH3), 4.69 (2H, m, N(CHH)2), 4.77 (2H, s, CH2Ph), 7.86 (2H, d, J=8.6 Hz, ArH), 7.20 (2H, d, J=8.6 Hz, ArH), 8.03 (1H, m, NHCON), 8.66 (1H, bs, OH), 10.31 (1H, s, NHOH).
MF C18H27N3O3S, MW 365.49
1H NMR (DMSO-d6, 400 MHz): δ (ppm) 1.01 (2H, dq, J=3.4 and 13.0 Hz), 1.14-1.20 (2H, m), 1.42-1.54 (1H, m), 1.62-1.75 (2H, m), 1.93 (2H, t, J=7.3 Hz, CH2CO), 2.77 (2H, m, N(CHH)2), 4.65 (2H, m, N(CHH)2), 4.77 (2H, s, CH2Ph), 7.17-7.34 (5H, m, ArH), 8.11 (1H, m, NHCON), 8.65 (1H, s, OH), 10.31 (1H, s, NHOH).
MF C17H25N3O2S, MW 335.46
MF C18H26FN3O3 MW 351.42
MF C18H26FN3O3 MW 351.42
1H NMR (DMSO-d6, 400 MHz): δ (ppm) 0.82-1.00 (2H, m), 1.14 (2H, m), 1.47 (3H, m), 1.64 (2H, m), 1.91 (2H, m), 2.53 (1H, m, N(CHH)2), 2.89-3.06 (3H, m, CH2CO, N(CHH)2), 3.78 (1H, d, J=12.5 Hz, N(CHH)2), 4.33 (1H, d, N(CHH)2), 4.81 (1H, m, NCHCH2), 7.24-7.61 (4H, m, ArH), 8.38 (1H, s, NH+), 8.64 (1H, s, OH), 10.31 (1H, s, NH).
MF C18H26FN3O3 MW 351.42
1H NMR (DMSO-d6, 400 MHz): δ (ppm) 0.91 (2H, dq, J=3.2 and 12.4 Hz), 1.09-1.17 (2H, m), 1.28-1.43 (1H, m) 1.48 (2H, quint, J=8.0 Hz), 1.53-1.63 (2H, m), 1.91 (2H, t, J=7.2 Hz, CH2CO), 2.64 (2H, m, N(CHH)2), 3.96 (2H, m, N(CHH)2), 4.62 (2H, s, PhCH2), 7.25 (1H, s, NCONH), 7.37 (1H, t, J=7.2 Hz, ArH), 7.63 (1H, t, J=7.2 Hz, ArH), 7.68-7.73 (1H, m, ArH), 7.92 (1H, d, J=8.0 Hz, ArH).
MF C18H24N4O4 MW 360.41
1H NMR (DMSO-d6, 400 MHz): δ (ppm) 1.03 (2H, dq, J=3.6 and 12.5 Hz), 1.17-1.27 (2H, m), 1.36-1.48 (1H, m), 1.53 (2H, m), 1.62-1.75 (2H, m), 1.94 (2H, t, J=7.3 Hz, CH2CO), 2.77 (2H, m, N(CHH)2), 4.13 (2H, m, N(CHH)2), 7.65 (2H, d, J=8.8 Hz, ArH), 7.99 (1H, d, J=8.8 Hz, ArH), 8.70 (1H, s, NHCON), 9.40 (1H, s, ThioH), 10.32 (1H, s, NHOH).
MF C18H23N5O3S, MW 389.47
1H NMR (DMSO-d6, 400 MHz): δ (ppm) 1.02 (2H, dq, J=3.6 and 12.6 Hz), 1.14-1.28 (2H, m), 1.37-1.46 (1H, m), 1.53 (2H, quin, J=7.6 Hz), 1.62-1.73 (2H, m), 1.94 (2H, t, J=7.3 Hz, CH2CO), 2.16 (3H, s, CH3), 2.23 (3H, s, CH3), 2.76 (2H, m, N(CHH)2), 4.11 (2H, m, N(CHH)2), 6.02 (1H, s, PyrH), 7.30 (2H, d, J=8.9 Hz, ArH), 7.55 (2H, d, J=8.9 Hz, ArH), 8.60 (1H, s, NHCON), 10.31 (1H, s, NHOH).
MF C21H29N5O3, MW 399.4
1H NMR (DMSO-d6, 400 MHz): δ (ppm) 1.02 (2H, dq, J=3.5 and 12.3 Hz), 1.14-1.26 (2H, m), 1.38-1.48 (1H, m), 1.52 (2H, quin, J=7.4 Hz), 1.61-1.71 (2H, m), 1.94 (2H, t, J=7.3 Hz, CH2CO), 2.71 (3H, s, CH3), 2.74 (2H, m, N(CHH)2), 4.12 (2H, m, N(CHH)2), 7.25 (1H, t, J=7.9 Hz, ArH), 7.46 (1H, t, J=7.4 Hz, ArH), 8.02 (1H, s, ArH), 8.54 (1H, s, ThiazH), 8.54 (1H, s, NHCON), 10.31 (1H, s, NHOH).
MF C20H26N4O3S, MW 402.51
1H NMR (DMSO-d6, 400 MHz): δ (ppm) 1.03 (2H, dq, J=3.2 and 12.4 Hz), 1.12-1.25 (2H, m), 1.35-1.48 (1H, m) 1.53 (2H, quint, J=7.6 Hz), 1.63-1.73 (2H, m), 1.94 (2H, t, J=7.2 Hz, CH2CO), 2.77 (2H, m, N(CHH)2), 4.14 (2H, m, N(CHH)2), 7.15-7.22 (1H, m, ArH), 7.39 (1H, s, ArH), 7.55-7.61 (1H, m, ArH), 7.71 (2H, t, J=9.6 Hz, ArH), 7.96 (1H, s, ArH), 8.61 (1H, s, NCONH), 10.32 (1H, s, NHOH).
MF C20H26N4O3, MW 370.45
1H NMR (DMSO-d6, 400 MHz): δ (ppm) 1.02 (2H, dq, J=3.2 and 12.4 Hz), 1.12-1.26 (2H, m), 1.35-1.47 (1H, m) 1.53 (2H, quint, J=8.0 Hz), 1.60-1.71 (2H, m), 1.94 (2H, t, J=7.2 Hz, CH2CO), 2.71 (2H, m, N(CHH)2), 4.10 (2H, m, N(CHH)2), 6.30 (1H, m, ArH), 7.09 (1H, dd, J=2.0 and 8.8 Hz, ArH), 7.21 (1H, s, ArH), 7.22-7.26 (1H, m, ArH), 7.56 (1H, s, ArH), 8.18 (1H, s, NCONH), 8.66 (1H, s, OH), 10.32 (1H, s, NHOH), 10.86 (1H, bs, IndNH).
MF C18H24N4O3, MW 344.41
1H NMR (DMSO-d6, 400 MHz): δ (ppm) 1.01 (2H, dq, J=3.7 and 12.6 Hz), 1.17-1.21 (2H, m), 1.35-1.46 (1H, m), 1.52 (2H, m), 1.59-1.69 (2H, m), 1.94 (2H, t, J=7.3 Hz, CH2CO), 2.17 (3H, s, CH3), 2.73 (2H, m, N(CHH)2), 4.06 (2H, m, N(CHH)2), 7.37-7.42 (1H, m, PyrH), 7.47-7.55 (5H, m, ArH), 8.50 (1H, s, NHCON), 10.32 (1H, s, NHOH).
MF C20H27N5O3, MW 385.46
1H NMR (DMSO-d6, 400 MHz): δ (ppm) 1.02 (2H, dq, J=3.9 and 12.7 Hz), 1.16-1.22 (2H, m), 1.37-1.47 (1H, m), 1.52 (2H, m), 1.62-1.68 (2H, m), 1.94 (2H, t, J=7.3 Hz, CH2CO), 2.74 (2H, m, N(CHH)2), 4.10 (2H, m, N(CHH)2), 6.21 (2H, t, J=2.1 Hz, PyrH), 7.25 (2H, t, J=2.1 Hz, PyrH), 7.40 (2H, d, J=9.0 Hz, ArH), 7.53 (2H, d, J=9.0 Hz, ArH), 8.50 (1H, s, OH), 10.32 (1H, s, NH).
MF C20H26N4O3, MW 370.44
1H NMR (DMSO-d6, 400 MHz): δ (ppm) 1.02 (2H, dq, J=3.9 and 12.8 Hz), 1.16-1.23 (2H, m), 1.38-1.47 (1H, m), 1.52 (2H, quin, J=7.4 Hz), 1.63-1.71 (2H, m), 1.94 (2H, t, J=7.3 Hz, CH2CO), 2.75 (2H, m, N(CHH)2), 4.11 (2H, m, N(CHH)2), 6.25 (2H, t, J=2.1 Hz, PyrH), 7.09 (1H, dd, J=1.4 and 7.8 Hz, ArH), 7.22 (2H, t, J=2.1 Hz, PyrH), 7.28 (1H, t, J=8.1 Hz, ArH), 7.33-7.38 (1H, m, ArH), 7.69 (1H, t, J=2.0 Hz, ArH), 8.57 (1H, s, OH), 10.32 (1H, s, NH).
MF C20H26N4O3, MW 370.44
1H NMR (DMSO-d6, 400 MHz): δ (ppm) 0.75-1.30 (4H, m), 1.45-1.80 (5H, m), 1.95 (2H, t, J=7.1 Hz, CH2CO), 2.55 (1H, t, J=13.0 Hz, CHHNH), 2.76 (2H, t, J=6.8 Hz, CH2CO), 2.95 (1H, t, J=13.0 Hz, CHHNH), 3.25 (2H, t, J=6.8 Hz, CH2NH), 3.75 (1H, d, J=13.0 Hz, CHHNH), 4.35 (1H, d, J=13.0 Hz, CHHNH), 4.70 (2H, s, CH2Ph), 7.55-7.75 (4H, m, ArH), 8.03 (2H, d, J=8.1 Hz, ArH), 8.24 (1H, d, J=8.1 Hz, ArH), 8.60 (1H, s, NH+), 8.65 (1H, bs, OH), 10.32 (1H, s, NHOH).
MF C23H31N3O3, MW: 397.51
1H NMR (DMSO-d6, 400 MHz): δ (ppm) 1.04 (2H, dq, J=3.2 and 12.4 Hz), 1.13-1.26 (2H, m), 1.35-1.47 (1H, m) 1.53 (2H, quint, J=7.6 Hz), 1.62-1.72 (2H, m), 1.94 (2H, t, J=7.2 Hz, CH2CO), 2.74 (2H, m, N(CHH)2), 4.13 (2H, m, N(CHH)2), 6.93 (1H, t, J=7.6 Hz, ArH), 7.04 (1H, t, J=7.6 Hz, ArH), 7.28 (1H, d, J=8.0 Hz, ArH), 7.33 (1H, s, ArH), 7.58 (1H, d, J=8.0 Hz, ArH), 8.08 (1H, t, J=5.6 Hz, NCONH), 8.65 (1H, s, OH), 10.32 (1H, s, NHOH), 10.64 (1H, bs, IndNH).
MF C18H24N4O3, MW 344.41
1H NMR (DMSO-d6, 400 MHz): δ (ppm) 0.92 (2H, dq, J=3.2 and 12.0 Hz), 1.10-1.20 (2H, m), 1.28-1.42 (1H, m) 1.49 (2H, quint, J=8.0 Hz), 1.53-1.62 (2H, m), 1.91 (2H, t, J=7.2 Hz, CH2CO), 2.63 (2H, m, N(CHH)2), 3.95 (2H, m, N(CHH)2), 4.43 (2H, s, PhCH2), 7.10 (1H, t, J=5.6 Hz, NCONH), 7.39 (1H, dd, J=2.0 and 8.4 Hz, ArH), 7.55 (1H, s, ArH), 7.97-8.04 (2H, d, J=5.2 Hz, ArH), 10.30 (1H, s, NHOH).
MF C19H24ClN3O3S, MW 409.93
1H NMR (DMSO-d6, 400 MHz): δ (ppm) 1.03 (2H, dq, J=3.2 and 11.6 Hz), 1.15-1.26 (2H, m), 1.35-1.47 (1H, m) 1.53 (2H, quint, J=8.0 Hz), 1.61-1.71 (2H, m), 1.94 (2H, t, J=7.2 Hz, CH2CO), 2.75 (2H, m, N(CHH)2), 4.13 (2H, m, N(CHH)2), 7.34 (1H, d, J=5.2 Hz, ArH), 7.42 (1H, dd, J=2.0 and 8.8 Hz, ArH), 7.67 (1H, d, J=5.2 Hz, ArH), 7.81 (1H, d, J=8.8 Hz, ArH), 8.02 (1H, d, J=2.0 Hz, ArH), 8.52 (1H, m, NCONH), 8.66 (1H, s, OH), 10.32 (1H, s, NHOH).
MF C18H23N3O3S, MW 361.46
1H NMR (DMSO-d6, 400 MHz): δ (ppm) 0.94 (2H, dq, J=3.2 and 12.0 Hz), 1.11-1.21 (2H, m), 1.30-1.43 (1H, m) 1.50 (2H, quint, J=8.0 Hz), 1.55-1.64 (2H, m), 1.92 (2H, t, J=7.2 Hz, CH2CO), 2.64 (2H, m, N(CHH)2), 3.97 (2H, m, N(CHH)2), 4.22 (2H, s, PhCH2), 7.00 (1H, m, NCONH), 7.26 (2H, d, J=8.0 Hz, ArH), 7.51-7.55 (1H, m, ArH), 7.60-7.66 (3H, m, ArH), 7.79-7.83 (1H, m, ArH), 8.65 (1H, s, OH), 10.31 (1H, s, NHOH).
MF C21H27N3O3S, MW 401.52
1H NMR (DMSO-d6, 400 MHz): δ (ppm) 0.90 (2H, dq, J=3.6 and 12.4 Hz), 1.10-1.19 (2H, m), 1.31-1.44 (1H, m) 1.50 (2H, quint, J=7.6 Hz), 1.55-1.63 (2H, m), 1.92 (2H, t, J=7.2 Hz, CH2CO), 2.64 (2H, m, N(CHH)2), 3.98 (2H, m, N(CHH)2), 4.29 (2H, s, PhCH2), 7.04 (1H, m, NCONH), 7.23 (1H, d, J=7.4 Hz, ArH), 7.33-7.42 (2H, m, ArH), 7.43-7.54 (4H, m, ArH), 7.61 (2H, d, J=7.4 Hz, ArH), 10.31 (1H, s, NHOH).
MF C23H29N3O3, MW 395.49
1H NMR (DMSO-d6, 400 MHz): δ (ppm) 0.95-1.29 (3H, m), 1.29-1.46 (1H, m) 1.54 (2H, quint, J=7.6 Hz), 1.58-1.68 (1H, m), 1.74-1.84 (2H, m), 1.94 (2H, t, J=7.2 Hz, CH2CO), 2.36-2.46 (1H, m, NCHH), 2.76 (1H, m, NCHH), 3.99 (2H, m, N(CHH)2), 6.90 (1H, t, J=7.6 Hz, ArH), 7.20 (2H, t, J=7.6 Hz, ArH), 7.43 (2H, d, J=7.6 Hz, ArH), 8.41 (1H, m, NCONH), 8.66 (1H, s, OH), 10.33 (1H, s, NHOH).
MF C16H23N3O3, MW 305.37
1H NMR (DMSO-d6, 400 MHz): δ (ppm) 0.82-0.94 (2H, m), 1.13-1.31 (3H, m), 1.44-1.57 (2H, m), 1.65-1.70 (2H, m), 1.90-1.95 (2H, t, J=7.6 Hz), 2.60 (1H, m), 2.86-2.99 (3H, m), 3.76 (1H, d, J=14.7 Hz), 4.09-4.14 (1H, m, NCHCH2CO), 4.32-4.40 (2H, m, NCH2Ph), 7.24-7.35 (5H, m, ArH), 8.10 (1H, brs, NH+), 8.69 (1H, s, OH), 8.80 (1H, s, NHCH2), 10.30 (1H, s, NH).
MF C20H30N4O4, MW 390.48
1H NMR (DMSO-d6, 400 MHz): 6?(ppm) 0.82-0.94 (2H, m), 1.13-1.31 (3H, m), 1.44-1.57 (2H, m), 1.65-1.70 (2H, m), 1.90-1.95 (2H, t, J=7.6 Hz), 2.60 (1H, m), 2.86-2.99 (3H, m), 3.76 (1H, d, J=14.7 Hz), 4.09-4.14 (1H, m, NCHCH2CO), 4.32-4.40 (2H, m, NCH2Ph), 7.24-7.35 (5H, m, ArH), 8.10 (1H, brs, NH+), 8.69 (1H, s, OH), 8.80 (1H, s, NHCH2), 10.30 (1H, s, NH).
MF C20H30N4O4, MW 390.48
1H NMR (DMSO-d6, 400 MHz): δ (ppm) 1.02-1.26 (4H, m), 1.39-1.57 (3H, m), 1.66 (2H, d, J=12.1 Hz), 1.94 (2H, t, J=7.3 Hz), 2.80 (2H, t, J=11.9 Hz, N(CHH)2), 4.13 (2H, d, J=13.2 Hz, N(CHH)2), 7.34-7.41 (2H, m, ArH), 7.53 (1H, s, ArH), 7.83-7.92 (2H, m, ArH), 8.55 (1H, m, NHCON), 8.66 (1H, s, OH), 10.32 (1H, s, NHOH).
MF C18H23N3O3S, MW 361.46
1H NMR (DMSO-d6, 400 MHz): δ (ppm) 0.93 (2H, dq, J=3.2 and 12.0 Hz), 1.10-1.19 (2H, m), 1.27-1.43 (1H, m) 1.49 (2H, quint, J=7.6 Hz), 1.54-1.63 (2H, m), 1.92 (2H, t, J=7.2 Hz, CH2CO), 2.33 (3H, s, CH3), 2.63 (2H, m, N(CHH)2), 3.94 (2H, m, N(CHH)2), 4.44 (2H, s, PhCH2), 7.15 (1H, t, J=5.6 Hz, NCONH), 7.29 (1H, m, ArH), 7.34 (1H, m, ArH), 7.67 (1H, d, J=8.0 Hz, ArH), 7.85 (1H, d, J=8.0 Hz, ArH), 10.30 (1H, s, NHOH).
MF C20H27N3O3S, MW 389.51
1H NMR (DMSO-d6, 400 MHz): δ (ppm) 0.90 (2H, dq, J=3.6 and 12.0 Hz), 1.09-1.18 (2H, m), 1.27-1.39 (1H, m) 1.48 (2H, quint, J=7.6 Hz), 1.52-1.61 (2H, m), 1.91 (2H, t, J=7.2 Hz, CH2CO), 2.35 (3H, s, CH3), 2.46-2.52 (2H, m), 2.50 (3H, s, CH3), 3.92 (2H, m, N(CHH)2), 4.14 (2H, s, PhCH2), 6.84 (1H, m, NCONH), 10.31 (1H, s, NHOH).
MF C16H26N4O3, MW 354.47
1H NMR (DMSO-d6, 400 MHz): δ (ppm) 1.01 (2H, dq, J=3.2 and 12.4 Hz), 1.13-1.24 (2H, m), 1.35-1.46 (1H, m) 1.52 (2H, quint, J=7.6 Hz), 1.58-1.75 (6H, m), 1.93 (2H, t, J=7.2 Hz, CH2CO), 2.50-2.59 (2H, m), 2.65-2.79 (4H, m), 4.04 (2H, m, N(CHH)2), 6.84 (1H, dd, J=2.4 and 6.4 Hz, ArH), 6.95-7.02 (2H, m, ArH), 7.78 (1H, s, OH), 10.32 (1H, s, NHOH).
MF C20H29N3O3, MW 359.46
1H NMR (DMSO-d6, 400 MHz): δ (ppm) 0.99 (2H, dq, J=3.6 and 12.4 Hz), 1.13-1.23 (2H, m), 1.32-1.46 (1H, m) 1.51 (2H, quint, J=7.6 Hz), 1.58-1.70 (2H, m), 1.93 (2H, t, J=7.2 Hz, CH2CO), 2.71 (2H, m, N(CHH)2), 3.84 (2H, m, Ph2CH2), 4.06 (2H, m, N(CHH)2), 7.05 (2H, d, J=8.4 Hz, ArH), 7.13-7.22 (3H, m, ArH), 7.23-7.29 (2H, m, ArH), 7.34 (2H, d, J=8.4 Hz, ArH), 8.34 (1H, s, NCONH), 8.65 (1H, s, OH), 10.31 (1H, s, NHOH).
MF C23H29N3O3, MW 395.50
1H NMR (DMSO-d6, 400 MHz): δ (ppm) 0.99 (2H, dq, J=3.6 and 12.4 Hz), 1.13-1.23 (2H, m), 1.32-1.46 (1H, m) 1.52 (2H, quint, J=7.6 Hz), 1.60-1.70 (2H, m), 1.92 (2H, t, J=7.6 Hz, CH2CO), 2.70 (2H, m, N(CHH)2), 4.07 (2H, m, N(CHH)2), 5.03 (2H, m, PhCH2O), 6.77 (2H, d, J=8.8 Hz, ArH), 7.27-7.47 (7H, m, ArH), 8.26 (1H, bs, NCONH), 8.65 (1H, s, OH), 10.32 (1H, s, NHOH).
MF C23H29N3O4, MW 411.49
1H NMR (DMSO-d6, 400 MHz): δ (ppm) 0.84-1.05 (2H, m), 1.09-1.15 (2H, m), 1.39-1.51 (3H, m), 1.64 (2H, m), 1.91 (2H, t, J=7.3 Hz), 2.53 (1H, m, N(CHH)2), 2.58-2.62 (2H, m, dt, J=2.8 and 7.1 Hz, NCHCH2), 2.95 (1H, t, J=12.7 Hz, N(CHH)2), 3.37 (2H, m, NCH2CH2) 3.79 (1H, d, J=13.2 Hz, N(CHH)2), 4.35 (1H, d, J=13.1 Hz, N(CHH)2), 7.40-8.06 (5H, m, ArH), 8.35 (1H, s, NH+), 8.66 (1H, s, OH), 10.30 (1H, s, NH).
MF C21H19N3O4S, MW 419.54
1H NMR (DMSO-d6, 400 MHz): δ (ppm) 0.84-1.01 (2H, m), 1.09-1.15 (2H, m), 1.47 (3H, m), 1.64 (2H, t, J=13.6 Hz), 1.76 (2H, m, COCH2CH2C), 1.91 (2H, t, J=7.3 Hz), 2.36 (2H, m, COCH2CH2C), 2.96 (1H, t, J=12.6 Hz), 3.27 (2H, m), 3.81 (1H, d, J=14.1 Hz, N(CHH)2), 4.36 (1H, d, J=13.3 Hz, N(CHH)2), 7.45 (2H, m, ArH), 7.92-8.06 (3H, m, ArH), 8.73 (1H, s, NH+), 10.30 (1H, s, NH).
MF C22H29N3O4S, MW 431.55
1H NMR (DMSO-d6, 400 MHz): δ (ppm) 0.88-0.95 (2H, m), 1.13-1.24 (2H, m), 1.37-1.54 (3H, m), 1.61-1.76 (2H, m), 1.80-1.96 (2H, m), 2.59-2.66 (1H, m, N(CHH)2), 2.99-3.11 (1H, m, N(CHH)2), 3.51-3.63 (2H, m), 4.03 (1H, d, J=13.5 Hz, N(CHH)2), 4.37 (1H, d, J=13.2 Hz, N(CHH)2), 4.55 (1H, m, CHNH2), 7.42-8.09 (5H, m, ArH), 8.26 (1H, s, NH3+), 8.61 (1H, s, OH), 9.03 (1H, s, NH+), 10.30 (1H, d, NH).
MF C21H28N4O4S, MW 432.54
1H NMR (DMSO-d6, 400 MHz): δ (ppm) 0.82-0.95 (2H, m), 1.13-1.31 (2H, m), 1.41-1.53 (3H, m), 1.66 (2H, m), 1.90-1.95 (2H, t), 2.52 (1H, m), 2.87-2.94 (3H, m), 3.71 (1H, d, J=14.0 Hz), 4.10-4.14 (1H, m, NCHCH2CO), 4.32-4.40 (1H, t, J=11.3 Hz), 4.81 (2H, s, NCH2Nap), 7.47-7.57 (4H, m, ArH), 7.86-8.04 (3H, m, ArH), 8.14 (1H, brs, NH3+), 8.65 (1H, s, OH), 8.82 (1H, s, NHCH2), 10.30 (1H, s, NH).
MF C24H32N4O4, MW 440.53
1H NMR (DMSO-d6, 400 MHz): δ (ppm) 0.97-1.10 (2H, m), 1.15-1.23 (2H, m), 1.36-1.48 (1H, m), 1.52 (2H, m), 1.63-1.73 (2H, m), 1.94 (2H, t, J=7.3 Hz, CH2CO), 2.76 (2H, m, N(CHH)2), 4.12 (2H, m, N(CHH)2), 4.38 (3H, s, CH3), 7.65 (2H, d, J=8.8 Hz, ArH), 7.90 (2H, d, J=8.8 Hz, ArH), 8.71 (1H, s, OH), 10.32 (1H, s, NH).
MF C18H25N7O3, MW 429.51
1H NMR (DMSO-d6, 400 MHz): δ (ppm) 0.92 (6H, d, J=6.7 Hz, CH(CH3)2), 1.02 (2H, dq, J=3.9 and 12.8 Hz), 1.16-1.22 (2H, m), 1.39-1.47 (1H, m), 1.52 (2H, quin, J=7.4 Hz), 1.63-1.71 (2H, m), 1.94 (2H, t, J=7.3 Hz, CH2CO), 2.31 (1H, m, CH(CH3)2), 2.76 (2H, m, N(CHH)2), 4.12 (2H, m, N(CHH)2), 4.53 (2H, d, J=7.1 Hz, CH2CH(CH3)2), 7.65 (2H, d, J=8.7 Hz, ArH), 7.91 (2H, d, J=8.7 Hz, ArH), 8.71 (1H, s, OH), 10.32 (1H, s, NH).
MF C21H31N7O3, MW 429.51
1H NMR (DMSO-d6, 400 MHz): δ (ppm) 1.02 (2H, dq, J=3.7 and 12.6 Hz), 1.16-1.21 (2H, m), 1.33-1.45 (1H, m), 1.52 (2H, quint, J=7.3 Hz), 1.62-1.70 (2H, m), 1.94 (2H, t, J=7.3 Hz, CH2CO), 2.25 (3H, s, CH3), 2.74 (2H, m, N(CHH)2), 4.11 (2H, m, N(CHH)2), 6.27 (1H, d, J=2.3 Hz, PyrH), 7.53 (2H, m, ArH), 7.61 (2H, m, ArH), 8.22 (1H, d, J=2.3 Hz, PyrH), 8.52 (1H, s, OH), 10.32 (1H, s, NH).
MF C20H27N5O3, MW 385.46
1H NMR (DMSO-d6, 400 MHz): δ (ppm) 1.01 (2H, dq, J=3.2 and 12.8 Hz), 1.11-1.26 (2H, m), 1.35-1.48 (1H, m) 1.52 (2H, quint, J=7.6 Hz), 1.61-1.74 (2H, m), 1.94 (2H, t, J=7.6 Hz, CH2CO), 2.17 (2H, quint, J=7.6 Hz, NCH2CH2CH2Ar), 2.76 (2H, m, N(CHH)2), 2.80 (6H, s, N(CH3)2), 3.02-3.12 (2H, m, NCH2CH2CH2Ar), 3.12-3.21 (2H, m, NCH2CH2CH2Ar), 4.13 (2H, m, N(CHH)2), 7.34-7.52 (1H, bs, NCONH), 7.52-7.66 (2H, m, ArH), 7.76-8.07 (2H, m, ArH), 8.69 (1H, bs, OH), 10.34 (1H, bs, NHOH).
MF C22H34N6O3, MW 430.54
1H NMR (DMSO-d6, 400 MHz): δ (ppm) 1.15-1.28 (4H, m), 1.49-1.58 (3H, m), 1.81 (2H, d, J=12.3 Hz), 3.26 (2H, t, J=12.3 Hz, N(CH2)2), 4.01 (2H, d, J=12.1 Hz, N(CH2)2), 7.22-7.38 (4H, m, ArH), 8.69 (1H, bs, OH), 10.34 (1H, bs, NHOH), 12.90 (1H, brs, H benzimidazol).
MF C16H22N4O2, MW 302.37
Histone deacetylase inhibitors are a class of potential therapeutic or prophylactic agents for pathological states caused by abnormal gene expression, such as inflammatory disorders, diabetes, complications of diabetes, homozygotic thalassaemia, fibrosis, cirrhosis, acute promyelocytic leukaemia (APL), transplant rejection, auto-immune diseases, protozoan infections, tumors and the like. In particular they are emerging as a new class of drugs with anti-tumor activity. The connection between some tumorous pathologies, such as carcinoma of the mammary, colon and lung, and acetylation levels of nuclear chromatin has been described. Drugs able to modulate chromatin remodelling are able to inhibit tumor proliferation and could provide new instruments for treating tumor pathologies in the not too distant future. Much experimental evidence leads to the belief that the main field of application of this class of drugs could be in combined therapies. The considerable tolerability that has emerged from the first clinical trials leads to the belief that this class of molecules lends itself to combined therapy with traditional drugs such as cytotoxic drugs, or with radiotherapy treatments or with the new generation antitumor agents. In particular, the present invention also provides combinations of compounds with histone deacetylase inhibitory activity of general formula (I) with one or more chemotherapeutic compounds chosen from the group: conventional cytotoxic agents, demethylating agents, cyclin dependent kinase inhibitors, differentiating agents, signal transduction modulators, HSP-90 antagonists, proteasome inhibitors. Preferred compounds are compounds chosen from the following groups: the conventional cytotoxic agents: fludarabine, gemcitabine, decitabine, paclitaxel, carboplatin and Topo I/II inhibitors to include Etoposide, Irinotecan, Topotecan, T-128 and Anthracyclines such as Doxorubicin, Sabarubicin, Daunorubicin;
the demethylating agents (demethylation of DNA): 5-aza-2′-deoxycytidine (5-aza-dC), 5-azacytidine;
the cyclin dependent kinase inhibitors: Flavopiridol, olomoucin, roscovitin, purvalanol B, GW9499, GW5181, CGP60474, CGP74514, AG12286, AG12275, Staurosporine, UCN-01;
the differentiating agents: retinoic acid and derivatives (All Trans Retinoic Acid, ATRA), 13-cis retinoic acid (CRA), PMA (phorbol myristate acetate); the signal transduction modulators: TRAIL, imatinib mesylate, LY-294002, bortezomib;
the HSP-90 antagonists: geldanamycin and its analogues (17-AAG);
the proteasome inhibitors: lactacystine, MG132, bortezomib (Velcade™).
The activity of the compounds as histone deacetylase (HDAC) inhibitors was measured using an in vitro acetylation assay. The compounds were then evaluated as inhibitors of proliferation of human tumor cell cultures. The overall data obtained are given in the table.
The assay (Fluor de Lys™ kit, BioMol) is divided into two steps: in the first step the substrate which comprises an acetylated lysine residue is reacted with the nuclear extract (HeLa) containing the enzymatic activity in the presence and absence of inhibitors. In the second step a fluorogenic reagent is added which highlights the deacetylated residues. A reduction in fluorescence is obtained where there has been inhibition of the deacetylase activity. The result is finally expressed as percent inhibition relative to the control without inhibitor at a concentration of 0.1 μM.
Human colon carcinoma cells HCT-116 were seeded onto 96-well plates in RPMI1640 culture medium with added 10% FBS and 2 mM glutamine. 24 hours after seeding, the compounds at different concentrations are added. All the compounds are diluted in DMSO such that the final concentrations on the cultures is no greater than 0.5%. 72 hours after addition of the compounds, cell viability is measured by means of the dye Alamar Blue. The result is expressed as percent survival of the treated relative to the control, treated with carrier alone.
Number | Date | Country | Kind |
---|---|---|---|
FI2005A000041 | Mar 2005 | IT | national |
FI2005A000239 | Nov 2005 | IT | national |
Filing Document | Filing Date | Country | Kind | 371c Date |
---|---|---|---|---|
PCT/EP2006/060687 | 3/14/2006 | WO | 00 | 9/7/2007 |