基于烟酸和 4-脒肟单元的伪肽

IF 1.4 4区化学 Q3 CHEMISTRY, ORGANIC Chemistry of Heterocyclic Compounds Pub Date : 2024-01-10 DOI:10.1007/s10593-024-03270-x

Volodymyr A. Tkachuk, Pavlo V. Reheda, Andriy V. Kozytskiy, Svitlana V. Shishkina, Olga V. Hordiyenko

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引用次数: 0

摘要

碳二亚胺介导的 4-氰基烟酸与 L-氨基酸甲酯的偶联主要形成双环化合物--2-(1-亚氨基-3-氧代-1,3-二氢-2H-吡咯并[3,4-c]吡啶-2-基)烷酸甲酯，这是 4-氮杂萘二亚胺的单亚氨基衍生物。在羟胺的作用下，它们进行吡咯烷循环开放，形成假肽--烟酸与第 4 位带有脒肟功能的氨基酸酯的偶联产物。

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Pseudopeptides based on nicotinic acid with 4-amidoxime unit

The carbodiimide-mediated coupling of 4-cyanonicotinic acid with L-amino acid methyl esters takes place with the predominant formation of bicyclic compounds – methyl 2-(1-imino-3-oxo-1,3-dihydro-2H-pyrrolo[3,4-c]pyridin-2-yl)alkanoates, which are monoimino derivatives of 4-azaphthalimide. Under the action of hydroxylamine they undergo pyrrolidine cycle opening with the formation of pseudopeptides – coupling products of nicotinic acid with amino acid esters bearing an amidoxime function at position 4.

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来源期刊

Chemistry of Heterocyclic Compounds 化学-有机化学

CiteScore

2.90

自引率

13.30%

发文量

审稿时长

1 months

期刊介绍： The international journal Chemistry of Heterocyclic Compounds publishes original papers, short communications, reviews, and mini-reviews dealing with problems in the field of heterocyclic chemistry in Russian and English. The Journal also publishes reviews and annotations on new books and brief reports on conferences in the field of heterocyclic chemistry, as well as commemoratives dedicated to prominent heterocyclic chemists.