A facile, alternative synthesis of 4'-thioarabinonucleosides and their biological activities

被引：58

作者：

Yoshimura, Y ^{[1
]}

Watanabe, M ^{[1
]}

Satoh, H ^{[1
]}

Ashida, N ^{[1
]}

Ijichi, K ^{[1
]}

Sakata, S ^{[1
]}

Machida, H ^{[1
]}

Matsuda, A ^{[1
]}

机构：

[1] HOKKAIDO UNIV,FAC PHARMACEUT SCI,KITA KU,SAPPORO,HOKKAIDO 060,JAPAN

来源：

JOURNAL OF MEDICINAL CHEMISTRY | 1997年 / 40卷 / 14期

关键词：

D O I：

10.1021/jm9701536

中图分类号：

R914 [药物化学];

学科分类号：

100701 ;

摘要：

4'-Thioarabinonucleosides, which are potential antiviral agents, were synthesized from D-glucose. 1,4-Anhydro-4-thioarabitol (8), which can be derived from diacetone glucose in nine steps, was subjected to Pummerer rearrangement after protection of the hydroxyl groups to give 1-O-acetyl-4-thioarabinose (II), which was condensed with nucleobases to give 4'-thioarabinonucleosides. The 5-substituted-4'-thioaraU (6a-e) derivatives showed anti-HSV-1 activity (ED50 = 0.43-3.50 mu g/mL). 4'-ThioaraG (6h) and 2,6-diaminopurine 4'-thioarabinonucleoside (4'-thioaraDAP, 6g) showed antiviral activity against several herpes viruses and were particularly potent against human cytomegalovirus (0.010 and 0.022 mu g/mL, respectively).

引用

页码：2177 / 2183

页数：7

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