5-O-Alkylated derivatives of 5-hydroxy-2'-deoxyuridine as potential antiviral agents. Anti-herpes activity of 5-propynyloxy-2'-deoxyuridine
- 1 February 1978
- journal article
- research article
- Published by American Chemical Society (ACS) in Journal of Medicinal Chemistry
- Vol. 21 (2) , 228-231
- https://doi.org/10.1021/jm00200a018
Abstract
Alkylation of 5-hydroxyuridine or 5-hydroxy-2''-deoxyuridine with various activated alkylating agents in the presence of 1 equivalent of NaOH gave a series of new nucleoside analogues which were evaluated for antiviral activity against vaccinia virus, herpes simplex-1 virus and vesicular stomatitis virus in primary rabbit kidney cells and human skin fibroblasts. One of these analogues, 5-propynyloxy-2''-deoxyuridine, was a potent inhibitor of herpes simplex virus. Structure-activity considerations suggest that the anti-herpes activity is dependent on the integrity of the acetylene group since substitution of phenyl, p-nitrophenyl, vinyl, carboxamido or carboxyl for the triple bond led to diminished antiviral activity.This publication has 2 references indexed in Scilit:
- Improved synthesis and in vitro antiviral activities of 5-cyanouridine and 5-cyano-2'-deoxyuridineJournal of Medicinal Chemistry, 1977
- Nucleosides. III. Studies on 5-Methylamino-2'-deoxyuridine as a Specific Antiherpes AgentJournal of Medicinal Chemistry, 1966