Activity against Mycobacterium tuberculosis of a new class of spirooxindolopyrrolidine embedded chromanone hybrid heterocycles

A new class of structurally intriguing heterocycles embedded with spiropyrrolidine, oxindole and chromanones was prepared by regio- and stereoselectively in quantitative yields using an intermolecular tandem cycloaddition protocol. The compounds synthesized were assayed for their anti-mycobacterial...

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Bibliographic Details
Published in:RSC advances 2024-04, Vol.14 (17), p.11604-11613
Main Authors: Alkaltham, Manal Fahad, Almansour, Abdulrahman I, Arumugam, Natarajan, Vagolu, Siva Krishna, Tønjum, Tone, Alaqeel, Shatha Ibrahim, Rajaratnam, Saiswaroop, Sivaramakrishnan, Venketesh
Format: Article
Language:English
Subjects:
Chemistry
Cycloaddition
Fluorine
Molecular docking
Mutation
Tuberculosis
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Summary:A new class of structurally intriguing heterocycles embedded with spiropyrrolidine, oxindole and chromanones was prepared by regio- and stereoselectively in quantitative yields using an intermolecular tandem cycloaddition protocol. The compounds synthesized were assayed for their anti-mycobacterial activity against ( ) H37Rv and isoniazid-resistant ( and promoter mutations) clinical isolates. Four compounds exhibited significant antimycobacterial activity against strains tested. In particular, a compound possessing a fluorine substituted derivative displayed potent activity at 0.39 μg mL against H37Rv, while it showed 0.09 μg mL and 0.19 μg mL activity against promoter and mutation isolates, respectively. A molecular docking study was conducted with the potent compound, which showed results that were consistent with the experiments.
ISSN:2046-2069
2046-2069
DOI:10.1039/d4ra01501k