Scaffold-hopping strategy toward calanolides with nitrogen-containing heterocycles

(+)-Calanolide A was the first natural product identified as an active agent against HIV-1 and Mycobacterium tuberculosis (Mtb). In devising a scaffold-hopping strategy of structure modification of (+)-calanolide A, we focused on the synthesis of calanolides by replacing ring D with various five or six membered nitrogen-containing heterocycles, hoping to get further understanding of the structure–activity relationship.

Graphical abstractWe explored the chemistry focused on replacing ring D in (+)-calanolide A with five or six membered nitrogen-containing heterocycles which may provide a novel scaffold for anti-HIV and anti-TB agents.Figure optionsDownload full-size imageDownload as PowerPoint slide