Synthesis and Antiviral Activities of 5-Substituted 1-(2-Deoxy-2-C-methylene-4-thio-β-D-erythro-pentofuranosyl)uracilst

Various 5-substituted 1-(2-deoxy-2-C-methylene-4-thio-β-D-erythropentofuranosyl)uracils (4′-thioDMDUs) were synthesized from D-glucose via sila-Pummerer-type glycosylation. All of the β-anomers of 5-substituted 4′-thioDMDU, except the 5-hydroxyethyl derivative, showed potent anti-HSV-1 activity (ED...

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Published inNucleosides & nucleotides Vol. 17; no. 1-3; pp. 65 - 79
Main Authors Satoh, Hiroshi, Yoshimura, Yuichi, Watanabe, Mikari, Ashida, Noriyuki, Ijichi, Katsushi, Sakata, Shinji, Machida, Haruhiko, Matsuda, Akira
Format Journal Article
LanguageEnglish
Published Taylor & Francis Group 01.01.1998
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Summary:Various 5-substituted 1-(2-deoxy-2-C-methylene-4-thio-β-D-erythropentofuranosyl)uracils (4′-thioDMDUs) were synthesized from D-glucose via sila-Pummerer-type glycosylation. All of the β-anomers of 5-substituted 4′-thioDMDU, except the 5-hydroxyethyl derivative, showed potent anti-HSV-1 activity (ED 50 = 0.016-0.096 μg/mL). 5-Ethyl- and 5-iodo-4′-thioDMDUs were also active against HSV-2 (ED 50 = 0.17 and 0.86 μg/mL, respectively). 5-Bromovinyl-4′-thioDMDU was particularly active against VZV (ED 50 = 0.013 μg/mL). This paper is dedicated to the memory of late Professor Tsujiaki Hata, who deceased on September 7, 1996.
ISSN:0732-8311
1525-7770
2332-3892
DOI:10.1080/07328319808005158