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通过Pictet-Spengler型反应从糖类一锅法合成羟基化生物碱。

One-Pot Synthesis of Hydroxylated Alkaloids from Sugars via a Pictet-Spengler-Type Reaction.

作者信息

Zhou Likai, Ma Na, Wu Jilai, Yang Weilin, Feng Lijing, Xie Song, Wang Lili, Chen Hua

机构信息

Key Laboratory of Chemical Biology of Hebei Province, College of Chemistry and Material Science, Hebei University, Baoding 071002, China.

Functional Polymer Materials R&D and Engineering Application Technology Innovation Center of Hebei, College of Chemical Engineering and Biotechnology, Xingtai University, Xingtai 054001, China.

出版信息

Molecules. 2024 Dec 3;29(23):5709. doi: 10.3390/molecules29235709.

Abstract

An efficient and convenient strategy has been successfully developed for the preparation of novel hydroxylated alkaloid derivatives (also called fused multicyclic iminosugars) from -toluenesulfonylated sugars through a Pictet-Spengler-type mechanism. This method is highly stereoselective, does not require metal catalysts, and capable of conducting gram level reactions (with a 53% yield). Some of such iminosugars had an intermediate antiproliferative effect on HCT116 tumor cells.

摘要

一种高效便捷的策略已成功开发出来,用于通过皮克特-施彭格勒型机制从对甲苯磺酰化糖制备新型羟基化生物碱衍生物(也称为稠合多环亚氨基糖)。该方法具有高度的立体选择性,不需要金属催化剂,并且能够进行克级反应(产率为53%)。其中一些亚氨基糖对HCT116肿瘤细胞具有中等的抗增殖作用。

https://cdn.ncbi.nlm.nih.gov/pmc/blobs/d138/11643748/462645f33145/molecules-29-05709-g001.jpg

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