Issue 17, 2024, Issue in Progress
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RSC Advances

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

Manal Fahad Alkaltham,a   Abdulrahman I. Almansour,a   Natarajan Arumugam, ORCID logo *a   Siva Krishna Vagolu,*bc   Tone Tønjum,bc   Shatha Ibrahim Alaqeel,d   Saiswaroop Rajaratname  and  Venketesh Sivaramakrishnane  

* Corresponding authors

a Department of Chemistry, College of Science, King Saud University, P.O. Box 2455, Riyadh 11451, Saudi Arabia
E-mail: anatarajan@ksu.edu.sa

b Department of Microbiology, University of Oslo, N-0316 Oslo, Norway
E-mail: vagolu000@gmail.com

c Department of Microbiology, Oslo University Hospital, N-0424 Oslo, Norway

d Department of Chemistry, College of Science, King Saud University (034), Riyadh 11495, Saudi Arabia

e Disease Biology Lab, Department of Biosciences, Sri Sathya Sai Institute of Higher Learning, Prasanthi Nilayam, Anantapur, Andhra Pradesh, India

Abstract

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 Mycobacterium tuberculosis (Mtb) H37Rv and isoniazid-resistant (katG and inhA promoter mutations) clinical Mtb isolates. Four compounds exhibited significant antimycobacterial activity against Mtb strains tested. In particular, a compound possessing a fluorine substituted derivative displayed potent activity at 0.39 μg mL−1 against H37Rv, while it showed 0.09 μg mL−1 and 0.19 μg mL−1 activity against inhA promoter and katG mutation isolates, respectively. A molecular docking study was conducted with the potent compound, which showed results that were consistent with the in vitro experiments.

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

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Article information

DOI
https://doi.org/10.1039/D4RA01501K
Article type
Paper
Submitted
27 Feb 2024
Accepted
02 Apr 2024
First published
11 Apr 2024
This article is Open Access
Creative Commons BY license

RSC Adv., 2024,14, 11604-11613

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

M. F. Alkaltham, A. I. Almansour, N. Arumugam, S. K. Vagolu, T. Tønjum, S. I. Alaqeel, S. Rajaratnam and V. Sivaramakrishnan, RSC Adv., 2024, 14, 11604 DOI: 10.1039/D4RA01501K

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