Structure−Activity Modifications of the HIV-1 Inhibitors (+)-Calanolide A and (−)-Calanolide B
- 1 January 1996
- journal article
- Published by American Chemical Society (ACS) in Journal of Medicinal Chemistry
- Vol. 39 (22) , 4507-4510
- https://doi.org/10.1021/jm9602827
Abstract
The delta 7,8 olefinic linkages within (+)-calanolide A(1) and (-)-calanolide B(2) were catalytically reduced to determine impact on the anti-HIV activity of the parent compounds. In addition, a series of structure modifications of the C-12 hydroxyl group in (-)-calanolide B was made to investigate the importance of that substituent to the HIV-1 inhibitory activity of these coumarins. A total of 14 analogs were isolated or prepared and compared to (+)-calanolide A and (-)-calanolide B in the NCI primary anti-HIV assay. While none of the compounds showed activity superior to the two unmodified leads, some structure-activity requirements were apparent from the relative anti-HIV potencies of the various analogs.Keywords
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