Synthesis and biological properties of 2'-deoxy-5-vinyluridine and 2'deoxy-5-vinylcytidine

Rapid and efficient syntheses for the preparation of 2'-deoxy-5-vinyluridine and 2'-deoxy-5-vinylcytidine are described starting from nucleoside precursors. Contrary to some previous reports, 2-deoxy-5-vinyluridine has be found to be quite stable under normal laboratory conditions but when...

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Bibliographic Details
Published in:Nucleic acids research 1982-09, Vol.10 (17), p.5285-5295
Main Authors: Rahim, S G, Duggan, M J, Walker, R T, Jones, A S, Dyer, R L, Balzarini, J, De Clercq, E
Format: Article
Language:English
Subjects:
Animals
Antiviral Agents - chemical synthesis
Antiviral Agents - therapeutic use
Deoxycytidine - analogs & derivatives
Deoxycytidine - chemical synthesis
Deoxycytidine - therapeutic use
Deoxyuridine - analogs & derivatives
Deoxyuridine - chemical synthesis
Deoxyuridine - therapeutic use
Drug Evaluation, Preclinical
Herpesviridae Infections - drug therapy
Herpesvirus
Leukemia L1210 - drug therapy
Mice
Plasmodium berghei
Structure-Activity Relationship
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Summary:Rapid and efficient syntheses for the preparation of 2'-deoxy-5-vinyluridine and 2'-deoxy-5-vinylcytidine are described starting from nucleoside precursors. Contrary to some previous reports, 2-deoxy-5-vinyluridine has be found to be quite stable under normal laboratory conditions but when tested in animals shows neither toxicity nor anti-leukemic (L1210 cells) or anti-parasitic (Plasmodium berghei) activity. 2'-Deoxy-5-vinylcytidine appears to polymerise readily. It is much less toxic to cell cultures than 2'-deoxy-5'vinyluridine but is almost as active against herpes virus replication (ID50:0.2 microgram/ml) for both type 1 and type 2 herpes virus (selectivity index:225).
ISSN:0305-1048
1362-4962