Syntheses and evaluation of macrocyclic engelhardione analogs as antitubercular and antibacterial agents.

ABSTRACT: The natural product engelhardione is an underexplored chemotype for developing novel treatments for bacterial infections; we therefore explored this natural product scaffold for chemical diversification and structure-activity relationship studies. Macrocyclic engelhardione and structural regioisomers were synthesized using a series of aldol condensations and selective hydrogenations to generate the 1,7-diarylheptan-3-one derivatives, followed by microwave-assisted intramolecular Ullmann coupling to afford a series of macrocyclic diaryl ether analogs. An extended macrocyclic chemical library was then produced by oxime formation, reductive amination and O-alkylation. Antibacterial evaluation revealed that the reductive amination derivatives 7b and 7d showed moderate activities (minimum inhib

SUBMITTER: Shen L 

PROVIDER: S-EPMC3696040 | biostudies-literature | 2013 Jun

REPOSITORIES: biostudies-literature