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Chemical synthesis of acyclic nucleoside phosphonate analogs linked with cyclic systems between the phosphonate and the base moieties.
Current Medicinal Chemistry ( IF 3.5 ) Pub Date : 2020-09-30 , DOI: 10.2174/0929867326666190620100217
Guang Huan Shen 1 , Joon Hee Hong 2
Affiliation  

The syntheses of acyclic nucleoside phosphonate (ANP) analogs linked with cyclic systems are described in the present review. The purpose of the review is to report the methodology of ANP analogs and to give an idea on the synthesis of a therapeutic structural feature of such analogs. The cyclopropane systems were mainly prepared by diazomethane cyclopropanation catalyzed by Pd(OAc)2, intramolecular alkylation, Kulinkovich cyclopropanation, and use of difluorocyclopropane, and so forth. The preparation of methylenecyclopropane system was made by diazoacetate cyclopropanation catalyzed by Rhodium followed by addition-elimination reactions. For the preparation of a variety of tethered 1,2,3-triazole systems, 1,3-dipolar cycloaddition between azidealkylphosphonates and propargylated nucleobases was mainly applied. The formation of various phosphonate moieties was achieved via phosphonylation of alkoxide, cross-coupling between BrZnCF2P (O)(OEt)2 with iodoalkens catalyzed by CuBr, Michaelis-Arbuzov reaction with phosphite, and Rh(II)-catalyzed O-H insertion, and so forth.



中文翻译:

化学合成无环核苷膦酸酯类似物,其与膦酸酯和碱基部分之间的环状系统连接。

在本综述中描述了与环状系统连接的无环核苷膦酸酯(ANP)类似物的合成。审查的目的是报告ANP类似物的方法,并就此类类似物的治疗结构特征的合成给出一个想法。环丙烷体系主要由Pd(OAc)2催化的重氮甲烷环丙烷化,分子内烷基化,库林科维奇环丙烷化和使用二氟环丙烷等制备。亚甲基环丙烷体系的制备是由铑催化重氮乙酸酯环丙烷化,然后进行加成-消除反应。为了制备各种束缚的1,2,3-三唑系,主要使用叠氮化物烷基膦酸酯和炔丙基化核碱基之间的1,3-偶极环加成。

更新日期:2020-10-30
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