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Glycerol Mediated Synthesis, Biological Evaluation, and Molecular Docking Study of 4‐(1 H ‐pyrazol‐4‐yl)‐polyhydroquinolines as Potent Antitubercular Agents
Author(s) -
Jamale Dattatraya K.,
Undare Santosh S.,
Valekar Navanath J.,
Sarkate Aniket P.,
Kolekar Govind B.,
Anbhule Prashant V.
Publication year - 2019
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.3438
Subject(s) - chemistry , pyrazole , mycobacterium tuberculosis , docking (animal) , dimedone , ammonium acetate , ethyl acetoacetate , glycerol , antimicrobial , minimum inhibitory concentration , stereochemistry , combinatorial chemistry , organic chemistry , catalysis , tuberculosis , high performance liquid chromatography , medicine , nursing , pathology
A series of 4‐(1 H ‐pyrazol‐4‐yl)‐polyhydroquinolines were synthesized through one‐pot four‐component Hantzsch condensation of 1,3‐diphenyl‐1 H ‐pyrazole‐4‐carbaldehydes, ammonium acetate, dimedone, and alkyl acetoacetate in glycerol as a green reaction medium. The structures of the compounds are verified by spectroscopic methods and screened for their antimicrobial activity against Mycobacterium tuberculosis H37RV strain. Almost all the synthesized derivatives reveal excellent antitubercular activity based on minimum inhibitory concentration. Especially the compounds 5h and 5k exhibit outstanding antitubercular activity with minimum inhibitory concentration 1.6 μg/mL. In addition, molecular docking study of synthesized scaffolds against enoyl‐acyl carrier protein reductase from M. tuberculosis was performed to propose the binding modes.