Stereospecific synthesis and antiviral properties of different enantiomerically pure carbocyclic 2'-deoxyribonucleoside analogs derived from common chiral pools: (+)-(1R,5S)- and (-)-(1S,5R)-2-oxabicyclo[3.3.0]oct-6-en-3-one
| Autor: | Eszter Baitz-Gács, L. Gruber, I. Tömösközi, L. Ötvös, Gyula Sági, J. Beres, E. De Clercq |
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| Rok vydání: | 1990 |
| Předmět: |
Bridged-Ring Compounds
Chemical Phenomena Bicyclic molecule Chemistry Stereochemistry Stereoisomerism Vaccinia virus Microbial Sensitivity Tests Antiviral Agents Deoxyribonucleoside Bridged Bicyclo Compounds Structure-Activity Relationship chemistry.chemical_compound Stereospecificity Deoxyadenosine Drug Discovery Simplexvirus Molecular Medicine Epimer Enantiomer Thymidine |
| Zdroj: | Journal of Medicinal Chemistry. 33:1353-1360 |
| ISSN: | 1520-4804 0022-2623 |
| DOI: | 10.1021/jm00167a011 |
| Popis: | 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 micrograms/mL, respectively] and HSV-2 (MIC: 2 and 20 micrograms/mL, respectively), but virtually inactive against TK- HSV-1 (MIC: 40 and 100 micrograms/mL, respectively). (+)-Carbathymidine was also active against vaccinia virus (2 micrograms/mL). None of the compounds had a specific effect on the replication of HIV or other RNA viruses. |
| Databáze: | OpenAIRE |
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