Protic Ionic Liquid Promoted One Pot Synthesis of 2‐amino‐4‐(phenyl)‐7‐methyl‐5‐oxo‐4H,5H‐pyrano[4,3‐b]pyran‐3‐carbonitrile Derivatives in Water and Their Antimycobacterial Activity

• Published in: Journal of heterocyclic chemistry Vol. 55; no. 4; pp. 1010 - 1023
• Main Authors: Mohire, Priyanka P., Chandam, Dattatray R., Patil, Reshma B., Kumbhar, Digambar R., Jadhav, Sunetra J., Patravale, Ajinkya A., Godase, Vijaya P., Ghosh, Jai S., Deshmukh, Madhukar B.
• Format: Journal Article
• Language: English
• Published: HOBOKEN Wiley 01.04.2018; Wiley Subscription Services, Inc
• Subjects: Amino acids; Benzaldehyde; Biological activity; Catalysis; Catalysts; Chemical synthesis; Chemistry; Chemistry, Organic; Derivatives; Ionic liquids; Ions; Malononitrile; Molecular docking; Physical Sciences; Recyclability; Scaffolds; Science & Technology; Tuberculosis; HIGHLY EFFICIENT CATALYST; MULTICOMPONENT REACTIONS; 3-COMPONENT SYNTHESIS; ACID; SOLVENTS; IN-VITRO EVALUATION; CONDENSATION; DIVERSITY; GREEN; ANTIMICROBIAL ACTIVITY
• ISSN: 0022-152X; 1943-5193
• DOI: 10.1002/jhet.3133

One pot three component reaction of 4‐hydroxy‐6‐methylpyran‐2‐one, 3‐methoxy benzaldehyde, and malononitrile in water using protic ionic liquid as a catalyst at room temperature afforded pyrano[4,3‐b]pyran derivatives. Protic ionic liquid has been proved to be an efficient and mild catalyst for the synthesis of pyrano[4,3‐b]pyran scaffolds due to their highly polar nature. The notable aspects of protic ionic liquid are easy availability, improved reaction rates, high product yields, simple workup procedure, recyclability, and reusability. Molecules docking studies have been performed on enzyme enoyl‐ACP‐reductase from Mycobacterium tuberculosis. The molecular docking simulation indicated plausible π‐alkyl and alkyl‐alkyl interactions between the amino acids and scaffolds. The synthesized derivatives have been evaluated for their in vitro antituberculotic activity against M. tuberculosis H37RV strain using Microplate Alamar Blue Assay method. Together, biological activity data and docking data showed that the tested scaffolds exhibited excellent antituberculotic activity.