Enantioselective synthesis and antiviral activity of purine and pyrimidine cyclopentenyl C-nucleosides

• Type of Material: Article
• Authors: Jagadeeshwar Rao, University of Georgia; Raymond Schinazi, Emory University; Chung K. Chu, University of Georgia
• Language: English
• Date: 2007-01-15
• Publisher: Elsevier Science Ltd.
• Publication Version: Final Published Version
• Copyright Statement: © 2006 Elsevier Ltd. All rights reserved.
• Final Published Version (URL): http://dx.doi.org/10.1016/j.bmc.2006.10.043
• Title of Journal or Parent Work: Bioorganic & Medicinal Chemistry
• Volume: 15
• Issue: 2
• Start Page: 839
• End Page: 846
• Grant/Funding Information: This research was supported in part by U.S. Public Health Service Research Grants UO19-AI-056540, 5R37-AI-25899, 5R37-AI-41980, 5P-AI-50409 from the National Institutes of Health and the Department of Veterans Affairs.
• Keywords: enantioselective synthesis; Science & Technology; Human immunodeficiency virus (HIV); Potent; Bond fission; In vitro; Chemistry, Organic; antiviral activity; Life Sciences & Biomedicine; Carbocyclic oxetanocin analogs; Biochemistry & Molecular Biology; Pharmacology & Pharmacy; carbocyclic C-nucleosides; Chemistry, Medicinal; Chemistry; Physical Sciences
• Research Categories: Health Sciences, Medicine and Surgery; Chemistry, Biochemistry; Health Sciences, Pharmacy

Abstract

The enantiomerically pure carbocyclic purine and pyrimidine C-nucleosides 1-4 were synthesized via the key intermediate, 2,3-(isopropylidenedioxy)-4-(trityloxymethyl)-4-cyclopenten-1-ol (5), which was prepared from d-ribose in eight steps. Synthesized compounds were evaluated as potential antiviral agents against HIV, SARSCoV, Punta Toro, West Nile, and Cowpox viruses. However, only 9-deazaneplanocin A (1) exhibited moderate anti-HIV activity.