An efficient synthesis of 3-fluoro-5-thio-xylofuranosyl nucleosides of thymine, uracil, and 5-fluorouracil as potential antitumor or/and antiviral agents

被引：25
作者：
Tsoukala, Evangelia
Agelis, George
Dolinsek, Jan
Botic, Tanja
Cencic, Avrelija
Komiotis, Dimitri [1 ]
机构：
[1] Univ Thessali, Organ Chem Lab, Dept Biochem & Biotechnol, Larisa 41221, Greece
[2] Univ Maribor, Fac Agr, Dept Microbiol Biochem & Biotechnol, Maribor, Slovenia
[3] Univ Maribor, Fac Med, Dept Biochem, Maribor, Slovenia
来源：
BIOORGANIC & MEDICINAL CHEMISTRY | 2007年 / 15卷 / 09期
关键词：
3-deoxy-3-fluoro-5-thio-xylofuranose; nucleoside; thymine; uracil; 5-fluorouracil; antiviral; antitumor agent;
D O I：
10.1016/j.bmc.2007.02.031
中图分类号：
Q5 [生物化学]; Q7 [分子生物学];
学科分类号：
071010 ; 081704 ;
摘要：
1,2:5,6-Di-O-isopropylidene-alpha-D-glucofuranose by the sequence of mild oxidation, reduction, fluorination, periodate oxidation, borohydride reduction, and sulfonylation gave 3-deoxy-3-fluoro-1,2-O-isopropylidene-5-O-p-toluenesulfonyl-alpha-D-xylofuranose (5). Tosylate 5 was converted to thioacetate derivative 6, which after acetolysis gave 1,2-di-O-acetyl-5-S-acetyl-3-deoxy-3-fluoro-5-thio-beta-xylofuranose (7). Condensation of 7 with silylated thymine, uracil, and 5-fluorouracil afforded nucleosides 1-(5-S-acetyl-3-deoxy-3-fluoro-5-thio-beta-D-xylofuranosyl) thymine (8), 1-(5-S-acetyl-3-deoxy-3-fluoro-5-thio-beta-D-xylofuranosyl) uracil (9), and 1-(5-S-acetyl-3-deoxy-3-fluoro-5-thio-beta-D-xylofuranosyl) 5-fluorouracil (10). Compounds 8, 9, and 10 are biologically active against rotavirus infection and the growth of tumor cells. (c) 2007 Elsevier Ltd. All rights reserved.
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页码：3241 / 3247
页数：7
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