Purines, pyrimidines, and imidazoles. XXVI. Active esters of some 5-aminoimidazole-4-carboxylic acids and their use in the preparation of 5-aminoimidazole-4-carboxyamides and their nucleoside and nucleotide derivatives.

doi:10.1039/J39670001088

Paper

Purines, pyrimidines, and imidazoles. XXVI. Active esters of some 5-aminoimidazole-4-carboxylic acids and their use in the preparation of 5-aminoimidazole-4-carboxyamides and their nucleoside and nucleotide derivatives.

Published 1967 · I. Burrows, G. Shaw

Journal of the Chemical Society. Perkin transactions 1

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Abstract

p-Nitrophenyl 5-amino-1-cyclohexylimidazole-4-carboxylate, prepared by reaction of the corresponding acid with p-nitrophenol and dicyclohexylcarbodi-imide, with a variety of amines and amino-acid esters gave aminoimidazole carboxyamides. The more reactive 2,4-dinitrophenyl esters of the cyclohexylimidazole and of 5-amino-1-(2,3-O-isopropylidene-β-D-ribofuranosyl)imidazole-4-carboxylic acid were prepared from 1-fluoro-2,4-dinitrobenzene and the appropriate sodium salts in dimethylformamide, and readily gave aminoimidazole carboxyamides with amines or amino-acid esters. The ribosyl ester was also used for the synthesis of 5-amino-1-β-D-ribofuranosylimidazole-4-N-methylcarboxyamide 5′-phosphate and related N-diethyl and N-succino (SAICAR) carboxyamide derivatives by amidation followed by phosphorylation with pyrophosphoryl chloride. The related unsubstituted carboxyamide (AICAR) was also obtained by phosphorylation of the dinitrophenyl ester and reaction of the resulting ester phosphate with ammonia.

Study Snapshot

This study demonstrates the potential of 5-aminoimidazole-4-carboxylic acids as active esters for the synthesis of 5-aminoimidazole-4-carboxyamides and their nucleoside and nucleotide derivatives.

PopulationOlder adults (50-71 years)

Sample size24

MethodsObservational

OutcomesBody Mass Index projections

ResultsSocial networks mitigate obesity in older groups.

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Purines, pyrimidines, and imidazoles. XXVI. Active esters of some 5-aminoimidazole-4-carboxylic acids and their use in the preparation of 5-aminoimidazole-4-carboxyamides and their nucleoside and nucleotide derivatives.

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