5-烷氧基甲基-3'-叠氮基-2',3-二脱氧尿苷的合成及其抗HIV活性

Synthesis and anti-HIV activity of 5-alkoxymethyl-3'-azido-2',3- dideoxyuridines.

作者信息

Abdel-Megied A E, Hansen P, Pedersen E B, Nielsen C, Nielsen C M

机构信息

Department of Chemistry, Odense University, Denmark.

出版信息

Arch Pharm (Weinheim). 1993 Jul;326(7):377-81. doi: 10.1002/ardp.19933260702.

DOI:10.1002/ardp.19933260702

PMID:8395167

Abstract

Methyl 3-azido-5-O-tert-butyldiphenylsilyl-2,3-dideoxy-D-erythro-furanosi de (3) was coupled with silylated 5-hydroxymethyluracil (1a) and its C1-C6 alkyl ethers 1b-g to give the corresponding protected nucleosides 4a-g which were deprotected with Bu4NF to afford 3-azido nucleosides 5a-g and 6a-g. The alpha-anomers 6f,g show moderate activity against HIV. No significant activity against HSV-1 was found for the compounds 5 and 6.

摘要

3-叠氮基-5-O-叔丁基二苯基甲硅烷基-2,3-二脱氧-D-赤藓糖呋喃糖苷（3）与硅烷化的5-羟甲基尿嘧啶（1a）及其C1-C6烷基醚1b-g偶联，得到相应的保护核苷4a-g，用四丁基氟化铵脱保护得到3-叠氮基核苷5a-g和6a-g。α-端基异构体6f,g对HIV显示出中等活性。化合物5和6对单纯疱疹病毒1型没有显著活性。