2. Academic Validation
  3. Synthesis and antiviral evaluation of cis-substituted cyclohexenyl and cyclohexanyl nucleosides

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

  • J Med Chem. 2005 Jan 27;48(2):450-6. doi: 10.1021/jm0493966.
Karine Barral 1,  Jérôme Courcambeck,  Gérard Pèpe,  Jan Balzarini,  Johan Neyts,  Erik De Clercq,  Michel Camplo
Affiliations

Affiliation

  • 1 Laboratoire des Matériaux Moléculaires et des Biomatériaux, GCOM2, UMR CNRS 6114, Université de la Méditerranée, case 901, 163 av. de Luminy, 13288 Marseille Cedex 9, France.
PMID: 15658858 DOI: 10.1021/jm0493966
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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