Synthesis and Anti-Tuberculosis Activity of Substituted 3,4-(dicoumarin-3-yl)-2,5-diphenyl Furans and Pyrroles

Abstract

Increasing rates of multi-drug resistant (MDR) and extremely-drug resistant (XDR) cases of tuberculosis (TB) strains are alarming, and eventually hampered an effective control of the pathogenic disease. In the present study, nine derivatives of 2,3-bis(2-oxochromen-3-yl)-1,4-diphenyl-butane-1,4-dione (11a–c) and 3,4-(dicoumarin-3-yl)-2,5-diphenyl furans and pyrroles (12a–f) have been synthesized successfully. The experimental data for the anti-tuberculosis activity (using MABA assay) of 2,3-bis(2-oxochromen-3-yl)-1,4-diphenyl-butane-1,4-dione (11a–c) revealed that, in this series, compound 11a showed a better minimum inhibitory concentration of 1.6 μg/mL against Mycobacterium tuberculosis (H37 RV strain) ATCC No-27294, which was better than the MIC value of Pyrazinamide-3.125 μg/mL, Streptomycin-6.25 μg/mL and Ciprofloxacin-3.125 μg/mL. Our synthesis and in-vitro studies thus pointed out the moderate to good anti-TB profiles of substituted furans and pyrroles.

Keywords

• tuberculosis
• <i>Mycobacterium</i>
• furans
• pyrroles