Synthesis and Anti-HIV-1 Activity of Carbocyclic Versions of Stavudine Analogues Using a Ring-closing Metathesis

Bulletin of the Korean chemical society

Joon Hee Hong¹  Lian Jin Liu¹  Ok Hyun Ko¹ 

关键词: Carbocyclic nucleoside;    Antiviral agents;    Ring-closing metathesis;    Claisen rearrangement;   

DOI  :  

学科分类：化学（综合）

来源: Korean Chemical Society

【 摘 要 】

An efficient synthetic route for carbocyclic versions of stavudine analogues and their evaluation on antiviral activity are described. The construction of an ethynylated quaternary carbon at the 4`-position of carbocyclic nucleosides was accomplished using Claisen rearrangement of 11 and ring-closing metathesis (RCM) of dienyne 14 as key transformations. An antiviral evaluation of the synthesized compounds, 20, 21, 22, and 25 against HIV-1, HSV-1, HSV-2, and HCMV showed that only the guanine analogue 25 is moderately active against HIV-1 in the MT-4 cell line (EC₅₀ = 11.91 レmol).

【 授权许可】

Unknown