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近期利用烯烃交叉复分解反应合成核苷膦酸类似物

Recent Synthesis of Nucleoside Phosphonate Analogs Using Olefin Cross-metathesis.

作者信息

Hong Joon Hee

机构信息

College of Pharmacy, Chosun University, Kwangju 501-759, Republic of Korea.

出版信息

Curr Med Chem. 2024 Apr 30. doi: 10.2174/0109298673280546240106123000.

Abstract

Nucleotide analogs known as acyclic and cyclic nucleoside phosphonates (ANPs and CNPs, respectively) have a variety of biological properties, including antibacterial, antiviral, antiparasitic, antineoplastic, and immunomodulatory. A strong reaction that has emerged in the last several decades has fundamentally changed our knowledge of the chemistry of nucleoside phosphonates. In particular, Olefin cross-metathesis (CM) has been a potent and practical synthesis route to produce functionalized olefins from essential alkene precursors. This review describes recent synthesis examples of ANPs and CNPs analogs using the Ru-catalyzed olefin cross-metathesis reactions. Olefin cross-metathesis reactions are performed in the olefinic parts of nucleoside and phosphonate produced by Grubbs, Hoveyda-Grubbs, and Nolan. This review presents a synthetic overview of a few chosen nucleosides with biological significance. Their biological activity results are briefly discussed.

摘要

被称为无环和环核苷膦酸酯(分别为ANP和CNP)的核苷酸类似物具有多种生物学特性,包括抗菌、抗病毒、抗寄生虫、抗肿瘤和免疫调节特性。在过去几十年中出现的一个重大反应从根本上改变了我们对核苷膦酸酯化学的认识。特别是,烯烃交叉复分解反应(CM)已成为从基本烯烃前体生产功能化烯烃的一种有效且实用的合成途径。本综述描述了使用钌催化的烯烃交叉复分解反应合成ANP和CNP类似物的最新实例。烯烃交叉复分解反应在由格拉布、霍维达-格拉布和诺兰制备的核苷和膦酸酯的烯部分中进行。本综述对一些具有生物学意义的选定核苷进行了合成概述。并简要讨论了它们的生物活性结果。

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