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An Efficient Green Synthesis of Some Functionalized Spiro Chromene Based Scaffolds as Potential Antitubercular Agents
Author(s) -
Khan Gulzar A.,
Naikoo Gowhar A.,
War Javeed A.,
Sheikh Imtiyaz A.,
Pandit Umar Jan,
Khan Imran,
Harit Amit K.,
Das Ratnesh
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.3091
Subject(s) - chemistry , acetone , acetic acid , reductase , combinatorial chemistry , docking (animal) , isoniazid , stereochemistry , proton nmr , carbon 13 nmr , organic chemistry , enzyme , medicine , tuberculosis , nursing , pathology
A facile multicomponent one pot synthesis of novel spiro [chromene‐2, 2‐pyrollidin]‐4 ′ ‐one derivatives 3a–l was conveniently carried out in acetic acid at feasible reaction conditions. The reaction mechanism operates through two key intermediates 3‐N‐aryliminocoumarin and coumarinylidene acetone. This protocol is an environmentally benign preparation and gives excellent yields of the target compounds (77–92%). The structure of new compounds were determined by spectroscopic techniques like FTIR, 1 H NMR, 13 C NMR, and MS. Docking studies against enoyl‐acyl carrier protein reductase predicts that the compounds bind at the active site with higher binding affinity values. The compound 3k (MIC, 10 μg/mL) shows comparable activity in reference with Isoniazid at the same concentrations against MT H37 Rv.