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Synthesis and antiviral evaluation of cis-substituted cyclohexenyl and cyclohexanyl nucleosides.

Journal of medicinal chemistry (2005-01-22)
Karine Barral, Jérôme Courcambeck, Gérard Pèpe, Jan Balzarini, Johan Neyts, Erik De Clercq, Michel Camplo
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.

MATERIALS
Product Number
Brand
Product Description

Sigma-Aldrich
3-Cyclohexene-1-carboxylic acid, 97%