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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.
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https://hal-amu.archives-ouvertes.fr/hal-02061654
Contributor : karine barral Connect in order to contact the contributor
Submitted on : Friday, March 8, 2019 - 11:46:23 AM
Last modification on : Thursday, August 4, 2022 - 10:09:00 AM

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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, American Chemical Society, 2005, 48 (2), pp.450-456. ⟨10.1021/jm0493966⟩. ⟨hal-02061654⟩

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