Synthesis of Mimics to 5-(2″-thienyl)-2′,3′-β-Dideoxyuridine Triphosphate

A series of 5′-amido derivatives of 5-(2″-thienyl)-2′,3′,5′-β-trideoxyuridine were prepared. The compounds were tested for their inhibition of cellular DNA polymerase α and α HIV-RT. The succinic fumaric and maleic acid derivatives of 5-(2″-thienyl)-2′,3′,5′-β-trideoxyuridine were investigated. None...

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Bibliographic Details
Published in:Antiviral chemistry & chemotherapy 1996-04, Vol.7 (2), p.101-107
Main Authors: Persson, T., Hörnfeldt, A.-B., Gronowitz, S., Johansson, N.G.
Format: Article
Language:English
Subjects:
Antibiotics. Antiinfectious agents. Antiparasitic agents
Antiviral agents
Biological and medical sciences
Deoxyribonucleic acid
DNA
DNA-directed DNA polymerase
Fumaric acid
HIV
Human immunodeficiency virus
Maleic acid
Medical sciences
Pharmacology. Drug treatments
Succinic acid
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Summary:A series of 5′-amido derivatives of 5-(2″-thienyl)-2′,3′,5′-β-trideoxyuridine were prepared. The compounds were tested for their inhibition of cellular DNA polymerase α and α HIV-RT. The succinic fumaric and maleic acid derivatives of 5-(2″-thienyl)-2′,3′,5′-β-trideoxyuridine were investigated. None of the compounds inhibited HIV-RT. The fumaric acid derivative inhibited DNA pol α with IC50 33 μg ml−1. The succinic acid derivative was about half as active with IC50 76 μg ml−1. The 5′-N-acyl derivatives also were structurally compared to the monomethyl ester of the triphosphate using the Sybyl program.
ISSN:2040-2066
0956-3202
2040-2066
DOI:10.1177/095632029600700207