Molecular hybridization of bioactives: synthesis and antitubercular evaluation of novel dibenzofuran embodied homoisoflavonoids via Baylis-Hillman reaction.

Abstract

A novel series of natural product like dibenzofuran embodied homoisoflavonoids [(E)-3-(dibenzo[b,d]furan-2-ylmethylene)chroman-4-ones] designed by molecular hybridization were synthesized in very good yields via a sequence of reactions involving base catalyzed Baylis-Hillmann (BH) reaction of 2-dibenzofuran carboxaldehyde and methyl acrylate; bromination of BH adduct; condensation of resulted allylic bromide with substituted phenols or 2-dibenzofuranol followed by cyclization. Among the all 11 new compounds screened for in vitro antimycobacterial activity against Mycobacterium tuberculosis H37Rv (MTB), (E)-3-(dibenzo[b,d]furan-2-ylmethylene)-6-fluorochroman-4-one (7f) and (E)-3-(dibenzo[b,d] furan-2-ylmethylene)-6-fluorochroman-4-one (7 g) were found to be active with MIC 12.5 μg/mL.

DOI: 10.1016/j.bmcl.2012.10.056

Cite this paper

@article{Yempala2012MolecularHO, title={Molecular hybridization of bioactives: synthesis and antitubercular evaluation of novel dibenzofuran embodied homoisoflavonoids via Baylis-Hillman reaction.}, author={Thirumal Yempala and D. Sriram and Perumal Yogeeswari and Srinivas Kantevari}, journal={Bioorganic & medicinal chemistry letters}, year={2012}, volume={22 24}, pages={7426-30} }