4'-硫代-2',3'-二脱氧核苷的合成及其抗HIV活性

Synthesis and anti-HIV activity of 4'-thio-2',3'-dideoxynucleosides.

作者信息

Secrist J A, Riggs R M, Tiwari K N, Montgomery J A

机构信息

Kettering-Meyer Laboratory, Southern Research Institute, Birmingham, Alabama 35255-5305.

出版信息

J Med Chem. 1992 Feb 7;35(3):533-8. doi: 10.1021/jm00081a015.

DOI:10.1021/jm00081a015

PMID:1738145

Abstract

A series of 2',3'-dideoxy-4'-thionucleoside analogues of purines and pyrimidines, including 4'-thioddI (17), 4'-thioddC (27), and 4'-thioAZT (34), were synthesized and evaluated for their inhibitory activity against human immunodeficiency virus (HIV). A stereospecific synthesis of the 2,3-dideoxy-4-thioribofuranosyl carbohydrate precursor 11 starting with L-glutamic acid is described. 2',3'-Dideoxy-4'-thiocytidine (27) displayed significant, but modest activity in vitro against human immunodeficiency virus.

摘要

合成了一系列嘌呤和嘧啶的2'，3'-二脱氧-4'-硫代核苷类似物，包括4'-硫代双脱氧肌苷（17）、4'-硫代双脱氧胞苷（27）和4'-硫代叠氮胸苷（34），并对它们抗人免疫缺陷病毒（HIV）的抑制活性进行了评估。描述了一种从L-谷氨酸开始立体定向合成2,3-二脱氧-4-硫代呋喃核糖碳水化合物前体11的方法。2'，3'-二脱氧-4'-硫代胞苷（27）在体外对人免疫缺陷病毒显示出显著但适度的活性。