Synthesis and antiviral properties of (Z)-5-(2-bromovinyl)-2'-deoxyuridine

(Z)-5-(2-Bromovinyl)uracil was obtained by photoisomerization of the E. isomer. Similarly, (E)-5-(2-bromovinyl)-2'-deoxyuridine gave the required Z isomer. (Z)-5-(2-Bromovinyl)-2'-deoxyuridine is much less active against herpes simplex virus type 1 (HSV-1) and somewhat less active against...

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Bibliographic Details
Published in:Journal of medicinal chemistry 1981-06, Vol.24 (6), p.759-760
Main Authors: Jones, A. Stanley, Rahim, S. George, Walker, Richard T, De Clercq, Erik
Format: Article
Language:English
Subjects:
Animals
Antiviral Agents
Bromodeoxyuridine - analogs & derivatives
Bromodeoxyuridine - chemical synthesis
Bromodeoxyuridine - pharmacology
herpes simplex virus 1
Rabbits
Simplexvirus - drug effects
Stereoisomerism
Structure-Activity Relationship
Vaccinia virus - drug effects
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Summary:(Z)-5-(2-Bromovinyl)uracil was obtained by photoisomerization of the E. isomer. Similarly, (E)-5-(2-bromovinyl)-2'-deoxyuridine gave the required Z isomer. (Z)-5-(2-Bromovinyl)-2'-deoxyuridine is much less active against herpes simplex virus type 1 (HSV-1) and somewhat less active against herpes simplex virus type 2 than is the E isomer. Both isomers show similar activity against vaccinia virus. Therefore, the highly potent and selective activity of (E)-5-(2-bromovinyl)-2'-deoxyuridine against HSV-1 is due to its E configuration.
ISSN:0022-2623
1520-4804
DOI:10.1021/jm00138a024