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.
|Number of pages||8|
|Journal||Journal of Medicinal Chemistry|
|Publication status||Published - 1990|
ASJC Scopus subject areas
- Organic Chemistry