Claims
- 1. A method of synthesizing highly substituted 2,4-dioxopiperdine compounds having the Formula I: wherein:R1 is selected from the group consisting of a standard natural amino acid side chain, CH3, CH(CH3)CH2CH3 and CH2Phenyl; R2 is selected from the group consisting of alkyl, substituted alkyl, aralkyl, phenyl and substituted aryl; R3 is selected from the group consisting of COOalkyl, CN, COloweralkyl, COaralkyl, COaryl, COfuryl and COthienyl; which method comprises, (a) preparing a compound of the formula: wherein R1-R3 are as described above, on a solid resin support, by reacting a compound of the formula: with an amidating reagent;(b) cleaving the compound from the solid resin support and methylating to yield an intermediate methyl ester compound of the formula: and,(c) condensing the intermediate methyl ester compound to provide the substituted 2,4-dioxopiperidine compounds of Formula I.
- 2. The method of claim 1, wherein:R1 is selected from the group consisting of a standard natural amino acid side chain, CH3, CH(CH3)CH2CH3 and CH2Phenyl; R2 is selected from the group consisting of alkyl, aralkyl, phenyl and substituted phenyl; where the substituents on the substituted phenyl group are selected from lower alkyl, halo, alkoxy, nitrile, cyano, alkoxycarbonyl, aryloxycarbonyl, nitro, furyl and substituted furyl; where the substituents on the furyl group are selected from alkyl, halo, alkoxy, alkoxycarbonyl, nitrile, aryloxycarbonyl, nitro, thienyl and substituted thienyl; where the substituents on the thienyl group are selected from lower alkyl, halo, alkoxy, nitrile, alkoxycarbonyl, aryloxycarbonyl, naphthyl and substituted naphthyl; where the substituents on the substituted naphthyl group are selected from lower alkyl, halo, alkoxy, nitrile, alkoxycarbonyl and aryloxycarbonyl; and, R3 is selected from the group consisting of COOalkyl, CN, COloweralkyl, CObenzyl,COsubstituted benzyl, COaryl, COfuryl and COthienyl; where aryl is phenyl, substituted phenyl or naphthyl.
- 3. The method of claim 1 wherein:(a) R1 is selected from the group consisting of CH3, CH(CH3)CH2CH3 and CH2Ph; (b) R2 is selected from the group consisting of phenyl, halophenyl, cyanophenyl and carboxyphenyl; and, (c) R3 is selected from the group consisting of COOC2H5, CN and COCH3.
- 4. A method for synthesizing a plurality of 2,4 dioxopiperidine compounds selected from those of claim 1 which comprises:(a) selecting a solid support comprising a plurality of compounds attached thereto selected from those of the formula: wherein R1 to R3 are as described above; and,(b) cleaving the compound from the solid resin support and methylating to yield a plurality of intermediate methyl ester compounds selected from those of the formula: and,(c) condensing said intermediate methyl ester compounds to provide the substituted 2,4-dioxopiperidine compounds of claim 1.
- 5. A chemical library consisting of a plurality of 2,4 dioxopiperidine compounds prepared by the method of claim 1.
- 6. A compound of the formula:
- 7. A compound of the formula:
- 8. A compound of the formula:
- 9. A compound of the formula:
- 10. A compound of the formula:
CROSS REFERENCE TO RELATED APPLICATION
This application claims the benefit of U.S. Provisional Application No. 60/129,211, filed Apr. 14, 1999.
Non-Patent Literature Citations (2)
Entry |
Caplus DN 132:12251, Wenying Chai et al, English Abstract, vol. 40 Issue 40, 1999.* |
Wenying Chai et al., Tetrahedron Letters 40(1999) 7185-7188, Solid Phase Synthesis of Ighly Substituted 2,4-Dioxopiperidines. |
Provisional Applications (1)
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Number |
Date |
Country |
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60/129211 |
Apr 1999 |
US |