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Protic Ionic Liquid Promoted One Pot Synthesis of 2‐amino‐4‐(phenyl)‐7‐methyl‐5‐oxo‐4 H ,5 H ‐pyrano[4,3‐ b ]pyran‐3‐carbonitrile Derivatives in Water and Their Antimycobacterial Activity
Author(s) -
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.
Publication year - 2018
Publication title -
journal of heterocyclic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.321
H-Index - 59
eISSN - 1943-5193
pISSN - 0022-152X
DOI - 10.1002/jhet.3133
Subject(s) - chemistry , ionic liquid , pyran , malononitrile , one pot synthesis , alkyl , catalysis , docking (animal) , benzaldehyde , combinatorial chemistry , organic chemistry , medicine , nursing
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 H 37 RV strain using Microplate Alamar Blue Assay method. Together, biological activity data and docking data showed that the tested scaffolds exhibited excellent antituberculotic activity.