氨基烷基化合成β-（4-氨基氨基）羧酸类缩氨酸和3-氨基-5,6-二氢脲嘧啶。

IF 2.7 3区化学 Q1 CHEMISTRY, ORGANIC

Organic & Biomolecular Chemistry Pub Date : 2025-07-10 DOI:10.1039/d5ob01075f

Anastasia A. Fesenko , Pavel E. Banschikov , Anatoly D. Shutalev

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引用次数: 0

摘要

提出了一种合成由α-氮杂氨基酸和β-氨基酸残基组成的拟肽物的新方法，即β-（4-氨基脲）-和β-（4-氨基脲）羧酸及其酯和肼。丙二酸二乙酯与2-未取代和2-甲基取代1-芳基-4-（甲苯基甲基）氨基脲进行酰胺烷基化反应，然后进行水解、脱羧和取代反应。酸促进β-（4-氨基脲）羧酸酰肼环化成3-氨基-5,6-二氢脲嘧啶衍生物的研究也进行了。基于DFT计算和动态核磁共振数据，讨论了3-乙酰氨基-5,6-二氢脲嘧啶的构象行为。

本文章由计算机程序翻译，如有差异，请以英文原文为准。

New synthesis of β-(4-semicarbazido)carboxylic acid-based peptidomimetics and 3-amino-5,6-dihydrouracils via an amidoalkylation protocol

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New synthesis of β-(4-semicarbazido)carboxylic acid-based peptidomimetics and 3-amino-5,6-dihydrouracils via an amidoalkylation protocol

A new approach to synthesize peptidomimetics consisting of α-aza-amino acid and β-amino acid residues, namely β-(4-semicarbazono)- and β-(4-semicarbazido)carboxylic acids, and their esters and hydrazides has been developed. The synthesis involves the amidoalkylation of diethyl malonate with 2-unsubstituted and 2-methyl-substituted 1-arylidene-4-(tosylmethyl)semicarbazides followed by hydrolysis, decarboxylation and substitution reactions. Acid-promoted cyclization of β-(4-semicarbazido)carboxylic acid hydrazides to derivatives of 3-amino-5,6-dihydrouracils has been also investigated. The conformational behavior of 3-acetylamino-5,6-dihydrouracils is discussed based on DFT calculations and dynamic NMR data.

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来源期刊

Organic & Biomolecular Chemistry 化学-有机化学

CiteScore

5.50

自引率

9.40%

发文量

1056

审稿时长

1.3 months

期刊介绍： Organic & Biomolecular Chemistry is an international journal using integrated research in chemistry-organic chemistry. Founded in 2003 by the Royal Society of Chemistry, the journal is published in Semimonthly issues and has been indexed by SCIE, a leading international database. The journal focuses on the key research and cutting-edge progress in the field of chemistry-organic chemistry, publishes and reports the research results in this field in a timely manner, and is committed to becoming a window and platform for rapid academic exchanges among peers in this field. The journal's impact factor in 2023 is 2.9, and its CiteScore is 5.5.