嘧啶类似物的3'-(4-硝基咪唑-1-基)-2',3'-二脱氧核苷的合成及其抗HIV的生物学评价。

Synthesis of 3'-(4-nitroimidazol-1-yl)-2',3'-dideoxynucleosides of pyrimidine analogues and their biological evaluation against HIV.

作者信息

Motawia M S, Pedersen E B, Suwinski J, Nielsen C M

机构信息

Department of Chemistry, Odense University, Denmark.

出版信息

Arch Pharm (Weinheim). 1990 Dec;323(12):949-53. doi: 10.1002/ardp.19903231203.

DOI:10.1002/ardp.19903231203

PMID:2096797

Abstract

Reaction of 1,5-di-O-acetyl-2,3-dideoxy-3-phthalimido-beta-D-erythro-pento-fur anose (1) with silylated pyrimidinediones 2a-c using the Lewis acid trimethylsilyl triflate as catalyst afforded nucleosides 3a-c and 4a,c which were deprotected with 33% methylamine/ethanol to give the corresponding 3-aminonucleosides 5a-c and 6. These were reacted with 1,4-dinitroimidazoles 7a,b to give the 3-imidazolyldideoxynucleosides 8a,b and 9a-f. At sub-toxic concentrations these compounds were ineffective against HIV-1.

摘要

1,5-二-O-乙酰基-2,3-二脱氧-3-邻苯二甲酰亚氨基-β-D-赤藓戊呋喃糖（1）与经硅烷化的嘧啶二酮2a - c在路易斯酸三甲基甲硅烷基三氟甲磺酸盐作为催化剂的条件下反应，得到核苷3a - c和4a,c，它们用33%甲胺/乙醇脱保护，得到相应的3-氨基核苷5a - c和6。这些化合物与1,4-二硝基咪唑7a,b反应，得到3-咪唑基二脱氧核苷8a,b和9a - f。在亚毒性浓度下，这些化合物对HIV-1无效。