Synthesis and biological activity of 5-(2,2-difluorovinyl)-2'-deoxyuridine
5-(2,2-Difluorovinyl)uracil (IV) was synthesized from 2,4-dimethoxy-5-bromopyrimidine by sequential formylation, difluoromethylenation, and removal of the 2- and 4-methyl groups. Condensation of the trimethylsilyl derivative of IV with protected D-erythro-pentofuranosyl chloride followed by separati...
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Published in | Journal of medicinal chemistry Vol. 30; no. 8; pp. 1494 - 1497 |
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Main Authors | , , |
Format | Journal Article |
Language | English |
Published |
Washington, DC
American Chemical Society
01.08.1987
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Subjects | |
Online Access | Get full text |
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Summary: | 5-(2,2-Difluorovinyl)uracil (IV) was synthesized from 2,4-dimethoxy-5-bromopyrimidine by sequential formylation, difluoromethylenation, and removal of the 2- and 4-methyl groups. Condensation of the trimethylsilyl derivative of IV with protected D-erythro-pentofuranosyl chloride followed by separation of anomers and deblocking gave 5-(2,2-difluorovinyl)-2'-deoxyuridine (V). Compound V was active against herpes simplex virus type 1 (HSV-1) infection as well as tumor cells transformed by the HSV-1 thymidine kinase gene. |
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Bibliography: | ark:/67375/TPS-XS1J0FM0-R istex:7CB95D94C75ACE8EDB1C9645F85C97A0A926A7B0 ObjectType-Article-1 SourceType-Scholarly Journals-1 ObjectType-Feature-2 content type line 23 |
ISSN: | 0022-2623 1520-4804 |
DOI: | 10.1021/jm00391a036 |