Issue 7, 2011
From the journal:

MedChemComm

Antimycobacterial activity of spirooxindolo-pyrrolidine, pyrrolizine and pyrrolothiazole hybrids obtained by a three-component regio- and stereoselective 1,3-dipolar cycloaddition†

Stephen Michael Rajesh,a   Subbu Perumal,*a   J. Carlos Menéndez,*b   Perumal Yogeeswaric  and  Dharmarajan Sriramc  

* Corresponding authors

a Department of Organic Chemistry, School of Chemistry, Madurai Kamaraj University, Madurai, India
E-mail: subbu.perum@gmail.com

b Departamento de Química Orgánica y Farmacéutica, Facultad de Farmacia, Universidad Complutense, Madrid, Spain
E-mail: josecm@farm.ucm.es

c Medicinal Chemistry & Antimycobacterial Research Laboratory, Pharmacy Group, Birla Institute of Technology & Science—Pilani, Hyderabad Campus, Jawahar Nagar, Hyderabad, Andhra Pradesh, India

Abstract

Spirooxindolo-pyrrolidine, pyrrolizine and pyrrolothiazole hybrid compounds were obtained in excellent yields from the regio- and stereoselective reaction between β-nitrostyrenes and non-stabilized azomethine ylides, generated in situ from isatin and phenylglycine/proline/thiaproline. These compounds were evaluated for their in vitro activity against Mycobacterium tuberculosisH37Rv (MTB). Eleven compounds were more active than pyrazinamide and one of them, namely 6′-(3-nitrophenyl)-7′-nitro-3′,6′,7′,7a′-tetrahydro-1′H-spiro-[indoline-3,5′-pyrrolo-[1,2-c]thiazol]-2-one, displayed a 7.6 μM MIC value, which represents a potency similar to that of the first-line anti-TB drug ethambutol and 6.7 times higher than that of pyrazinamide.

Graphical abstract: Antimycobacterial activity of spirooxindolo-pyrrolidine, pyrrolizine and pyrrolothiazole hybrids obtained by a three-component regio- and stereoselective 1,3-dipolar cycloaddition

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Article information

DOI
https://doi.org/10.1039/C0MD00239A
Article type
Concise Article
Submitted
29 Nov 2010
Accepted
06 Apr 2011
First published
12 May 2011

Med. Chem. Commun., 2011,2, 626-630

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Antimycobacterial activity of spirooxindolo-pyrrolidine, pyrrolizine and pyrrolothiazole hybrids obtained by a three-component regio- and stereoselective 1,3-dipolar cycloaddition

S. M. Rajesh, S. Perumal, J. C. Menéndez, P. Yogeeswari and D. Sriram, Med. Chem. Commun., 2011, 2, 626 DOI: 10.1039/C0MD00239A

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