Microwave assisted synthesis and anti-influenza virus activity of 1-adamantyl substituted N-(1-thia-4-azaspiro[4.5]decan-4-yl)carboxamide derivatives |
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Authors: | Füsun Göktaş Evelien Vanderlinden Lieve Naesens Nesrin Cesur Zafer Cesur |
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Institution: | 1. Istanbul University, Faculty of Pharmacy, Department of Pharmaceutical Chemistry, 34116 Beyaz?t, Istanbul, Turkey;2. Rega Institute for Medical Research, University of Leuven, B-3000 Leuven, Belgium |
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Abstract: | A microwave-assisted three-component one-pot cyclocondensation method was applied for the synthesis of novel N-(1-thia-4-azaspiro4.5]decan-4-yl)carboxamide compounds carrying an adamantyl moiety. The structures of the compounds were confirmed by spectral and elemental analysis. All compounds were evaluated for antiviral activity against influenza A (H1N1 and H3N2) and influenza B virus in MDCK cell cultures. The compounds displayed a confined structure-activity relationship. The N-(2,8-dimethyl-3-oxo-1-thia-4-azaspiro4.5]dec-4-yl)adamantane-1-carboxamide 3b was the most potent inhibitor antiviral EC50: 1.4 μM against influenza A/H3N2 virus]. Its strong inhibitory effect in a virus hemolysis assay supports that 3b acts as an influenza virus fusion inhibitor by preventing the conformational change of the influenza virus hemagglutinin at low pH. |
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