Unexpected formation of 4,5-dihydro-1H-pyrazolo[3,4-b]pyridine derivatives as a potent antitubercular agent and its evaluation by green chemistry metrics

Abstract

The present study describes L-hydroxy proline catalyzed unpredicted formation of 4,5-dihydro-1H-pyrazolo[3,4-b]pyridines instead of expected 4,7-dihydro-1H-pyrazolo[3,4-b]pyridines in aqueous ethanol at ambient temperature through one-pot three-component reaction. Furthermore, this protocol was evaluated using green chemistry metrics indicating green relevance of the present synthetic methodology. Most of the synthesized compounds were evaluated for their antitubercular activity against Mycobacterium tuberculosis H37RV strain, showing excellent results based on minimum inhibitory concentrations (MIC). Among the screened derivatives 4f, 4i, and 4j exhibited antitubercular activity with promising MIC value of 1.6 μg/mL.