Stereospecific synthesis and antiviral properties of different enantiomerically pure carbocyclic 2′-deoxyribonucleoside analogues derived from common chiral pools: (+)-(1R,5S)- and (-)-(1S,5R)-2-oxabicyclo[3.3.0]oct-6-en-3-one

J. Béres, Gy Sági, I. Tömösközi, L. Gruber, E. Gács-Baitz, L. Ötvös, E. De Clercq

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Abstract

Enantiomerically pure (+)- and (-)-carbocyclic thymidine, (-)-carbocyclic 3′-epi-thymidine, (+)-carbocyclic 3′-deoxy-3′-azidothymidine, (+)-carbocyclic 2,3′-O-anhydrothymidine, (+)-carbocyclic 3′-O,6′-methylenethymidine, and (+)-(6′S)-carbocyclic 6′-methylthymidine were synthesized in a stereospecific manner from common chiral pools of (+)-(1R,5S)- and (-)-(1S,5R)-2-oxabicyclo[3.3.0]oct-6-en-3-one and evaluated for antiviral activity. (+)-Carbathymidine and, to a lesser extent, (+)-carbocyclic 2′-deoxyadenosine proved to be effective against HSV-1 [minimum inhibitory concentration (MIC): 0.2 and 2 μg/mL, respectively] and HSV-2 (MIC: 2 and 20 μg/mL, respectively), but virtually inactive against TK- HSV-1 (MIC: 40 and 100 μg/mL, respectively). (+)-Carbathymidine was also active against vaccinia virus (2 μg/mL). None of the compounds had a specific effect on the replication of HIV or other RNA viruses.

Original languageEnglish
Pages (from-to)1353-1360
Number of pages8
JournalJournal of Medicinal Chemistry
Volume33
Issue number5
Publication statusPublished - 1990

ASJC Scopus subject areas

  • Organic Chemistry

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