5-取代的1-(2-脱氧-2-C-亚甲基-4-硫代-β-D-赤型戊呋喃糖基)尿嘧啶的合成及其抗病毒活性

Synthesis and antiviral activities of 5-substituted 1-(2-deoxy-2-C-methylene-4-thio-beta-D-ertythro-pentofuranosyl)uracils.

作者信息

Satoh H, Yoshimura Y, Watanabe M, Ashida N, Ijichi K, Sakata S, Machida H

机构信息

Biochemicals Division, Yamasa Corporation, Chiba, Japan.

出版信息

Nucleosides Nucleotides. 1998 Jan-Mar;17(1-3):65-79. doi: 10.1080/07328319808005158.

DOI:10.1080/07328319808005158

PMID:9708341

Abstract

Various 5-substituted 1-(2-deoxy-2-C-methylene-4-thio-beta-D-erythro-pentofuranosyl)uracils (4'-thioDMDUs) were synthesized from D-glucose via sila-Pummerer-type glycosylation. All of the beta-anomers of 5-substituted 4'-thioDMDU, except the 5-hydroxyethyl derivative, showed potent anti-HSV-1 activity (ED50 = 0.016-0.096 microgram/mL). 5-Ethyl- and 5-iodo-4'-thioDMDUs were also active against HSV-2 (ED50 = 0.17 and 0.86 microgram/mL, respectively). 5-Bromovinyl-4'-thioDMDU was particularly active against VZV (ED50 = 0.013 microgram/mL).

摘要

通过硅-Pummerer型糖基化反应，从D-葡萄糖合成了各种5-取代的1-(2-脱氧-2-C-亚甲基-4-硫代-β-D-赤型戊呋喃糖基)尿嘧啶(4'-硫代DMDU)。除5-羟乙基衍生物外，5-取代4'-硫代DMDU的所有β-异头物均表现出强大的抗HSV-1活性(ED50 = 0.016-0.096微克/毫升)。5-乙基-和5-碘-4'-硫代DMDU对HSV-2也有活性(ED50分别为0.17和0.86微克/毫升)。5-溴乙烯基-4'-硫代DMDU对VZV特别有活性(ED50 = 0.013微克/毫升)。