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Issue 1, 2015
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A strategic approach to the synthesis of functionalized spirooxindole pyrrolidine derivatives: in vitro antibacterial, antifungal, antimalarial and antitubercular studies

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Abstract

A series of spiro[pyrrolidin-2,3′-oxindoles] has been synthesized by exo-selective 1,3-dipolar cycloaddition reaction of a stabilized azomethine ylide, generated in situ by thermal [1,5]-prototropy, across various (E)-3-arylidene-1-phenyl-pyrrolidine-2,5-diones. The stereochemistry of these N-heterocycles has been confirmed using an X-ray diffraction study. To rationalize the observed regio- and stereoselectivity, DFT calculations at the B3LYP/6-31G(d,p) level were employed. It was found that this reaction preferentially affords the kinetic product. The compounds have been screened for their in vitro antibacterial, antifungal, antimalarial and antitubercular activities. Several compounds exhibited good activities comparable to those of established standard drugs.

Graphical abstract: A strategic approach to the synthesis of functionalized spirooxindole pyrrolidine derivatives: in vitro antibacterial, antifungal, antimalarial and antitubercular studies

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Publication details

The article was received on 18 Jun 2014, accepted on 27 Oct 2014 and first published on 27 Oct 2014


Article type: Paper
DOI: 10.1039/C4NJ01008F
Citation: New J. Chem., 2015,39, 520-528
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    A strategic approach to the synthesis of functionalized spirooxindole pyrrolidine derivatives: in vitro antibacterial, antifungal, antimalarial and antitubercular studies

    S. Haddad, S. Boudriga, T. N. Akhaja, J. P. Raval, F. Porzio, A. Soldera, M. Askri, M. Knorr, Y. Rousselin, M. M. Kubicki and D. Rajani, New J. Chem., 2015, 39, 520
    DOI: 10.1039/C4NJ01008F

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