新型异头支链碳环核苷的合成与抗病毒活性

Synthesis and antiviral activity of novel anomeric branched carbocyclic nucleosides.

作者信息

Kim Aihong, Hong Joon Hee

机构信息

College of Pharmacy, Chosun University, Kwangju, Korea.

出版信息

Arch Pharm Res. 2005 Oct;28(10):1105-10. doi: 10.1007/BF02972969.

DOI:10.1007/BF02972969

PMID:16276962

Abstract

Novel anomeric branched carbocyclic nucleosides were synthesized from 1,3-dihydroxy acetone. 4'-Hydroxymethyl was installed by [3,3]-sigmatropic rearrangement reaction and 1'-methyl group was introduced by carbonyl addition of methylmagnesium bromide. The coupling of nucleosidic bases and desilylation afforded a series of novel nucleosides. The synthesized compounds 16-19 were evaluated for their antiviral activity against HIV-1, HSV-1, HSV-2, and EMCV. Compounds 16 and 19 exhibit toxicity non-related to any anti-HIV-1 activity.

摘要

新型异头支链碳环核苷由1,3 - 二羟基丙酮合成。通过[3,3] - 迁移重排反应引入4'-羟甲基，并通过溴化甲基镁的羰基加成引入1'-甲基。核苷碱基的偶联和去甲硅烷基化反应得到了一系列新型核苷。对合成的化合物16 - 19进行了抗HIV - 1、HSV - 1、HSV - 2和EMCV的抗病毒活性评估。化合物16和19表现出与任何抗HIV - 1活性无关的毒性。