Synthesis and Antiviral Evaluation of Cis-Substituted Cyclohexenyl and Cyclohexanyl Nucleosides - Aix-Marseille Université Access content directly
Journal Articles Journal of Medicinal Chemistry Year : 2005

Synthesis and Antiviral Evaluation of Cis-Substituted Cyclohexenyl and Cyclohexanyl Nucleosides

Abstract

Starting from commercially available (rac)-3-cyclohexene-1-carboxylic acid, a series of purine and pyrimidine cis-substituted cyclohexenyl and cyclohexanyl nucleosides were synthesized through a key Mitsunobu reaction. Antiviral evaluations were performed on HIV, coxsackie B3, and herpes viruses (HSV-1, HSV-2, VZV, HCMV). Three compounds showed moderate activity against HSV-1 and coxsackie viruses. Specific computer modeling studies were performed on HSV-1 thymidine kinase in order to understand the enzyme activation of an analogue showing moderate antiviral activity.

Dates and versions

hal-02061654 , version 1 (08-03-2019)

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Karine Barral, Jérôme Courcambeck, Gérard Pèpe, Jan Balzarini, Johan Neyts, et al.. Synthesis and Antiviral Evaluation of Cis-Substituted Cyclohexenyl and Cyclohexanyl Nucleosides. Journal of Medicinal Chemistry, 2005, 48 (2), pp.450-456. ⟨10.1021/jm0493966⟩. ⟨hal-02061654⟩
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