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通过不对称多组分反应(AMCRs)设计与合成新型杂环C-糖缀合物以及碳连接糖和杂环氨基酸。

Design and synthesis of new classes of heterocyclic C-glycoconjugates and carbon-linked sugar and heterocyclic amino acids by asymmetric multicomponent reactions (AMCRs).

作者信息

Dondoni Alessandro, Massi Alessandro

机构信息

Dipartimento di Chimica, Laboratorio di Chimica Organica, Università di Ferrara, Via L. Borsari 46, I-44100 Ferrara, Italy.

出版信息

Acc Chem Res. 2006 Jul;39(7):451-63. doi: 10.1021/ar068023r.

Abstract

While chemical efficiency relies on several factors, the multicomponent reaction (MCR) approach was considered as a powerful synthetic tool for preparing target molecules of biological relevance in an efficient manner. Four classes of new bioactive molecules were designed and synthesized by asymmetric MCRs, in some cases with the cooperation of polymer-assisted solution-phase (PASP) technique. These include (a) C-glycosyl dihydropyrimidines and dihydropyridines via Biginelli and Hantzsch cyclocondensations, (b) C-glycosyl beta-amino acids via Mannich- and Reformatsky-type reactions, (c) C-glycosyl beta-lactams via Staudinger reaction, and (d) heterocyclic alpha-amino acids (glycine and alanine) via the Biginelli and Hantzsch reactions.

摘要

虽然化学效率取决于几个因素,但多组分反应(MCR)方法被认为是一种强大的合成工具,可有效地制备具有生物学相关性的目标分子。通过不对称MCR设计并合成了四类新型生物活性分子,在某些情况下还借助了聚合物辅助溶液相(PASP)技术。这些包括:(a)通过Biginelli和Hantzsch环缩合反应得到的C-糖基二氢嘧啶和二氢吡啶;(b)通过曼尼希和雷福尔马茨基型反应得到的C-糖基β-氨基酸;(c)通过施陶丁格反应得到的C-糖基β-内酰胺;以及(d)通过Biginelli和Hantzsch反应得到的杂环α-氨基酸(甘氨酸和丙氨酸)。

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