TY - JOUR T1 - Amide-linked monocarbonyl curcumin analogues: efficient synthesis, antitubercular activity and molecular docking study JF - Polycyclic Aromatic Compounds Y1 - 2022 A1 - Subhedar, Dnyaneshwar D. A1 - Shaikh, Mubarak H. A1 - Nagargoje, Amol A. A1 - Akolkar, V. Satish A1 - Bhansali, Sujit G. A1 - Sarkar, Dhiman A1 - Shingate, Bapurao B. KW - antimycobacterial activity KW - Bis (arylidene)-4-piperidones KW - Cytotoxicity KW - Ionic liquid KW - Molecular docking Study AB -

An approach toward the synthesis of novel conjugates of 3,5-bis (arylidene)-4-piperidones (DAP) pharmacophore with amide-linkage has been developed via one-pot multicomponent reaction of aryl aldehydes, piperidinone and 2-chloro-N-phenylacetamide using [Et3NH][HSO4] as a catalyst/medium. Both substitutions on arylidene rings and piperidinone nitrogen (substituted 2-chloro-N-phenylacetamide) were varied. The synthesized conjugates were evaluated for their in vitro antitubercular activity against M. tuberculosis H37Ra (MTB) and M. bovis BCG strains. Among the series, compounds 4f, 4g, 4i and 4j showed remarkable broad spectrum antitubercular activity with low IC50 values. Furthermore, computer docking simulations, for the most active conjugates were performed with the active site of mycobacterial enoyl-acyl carrier protein reductase (InhA) support the antitubercular activity. Lower cytotoxicity, high potency and promising activity against MTB and M. Bovis BCG suggest that amide linked DAP could serve as good leads for further modifications and development.

VL - 45 IS - 5 U3 -

Foreign

U4 -

2.195

ER -