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Issue 2, 2013
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Expeditious synthesis, antibacterial activity evaluation and GQSAR studies of 3-bisoxindoles, 2-oxindolyl-2-hydroxyindan-1,3-diones and 2-oxindolyl-2-hydroxyacenaphthylen-1-ones

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Abstract

The rhodium(II)-catalyzed one-pot three-component reaction of 3-diazooxindole, benzyl alcohol and isatin or ninhydrin or acenaphthenequinone was explored to synthesize 3-bisoxindoles, 2-oxindolyl-2-hydroxyindan-1,3-diones and 2-oxindolyl-2-hydroxyacenaphthylen-1-ones with vicinal stereo centres, respectively through oxonium ylides. Their antibacterial activities against Staphylococcus aureus NCIM 5021, Escherichia coli NCIM 2931, Pseudomonas aeruginosa NCIM 5029, Salmonella typhimurium NCIM 2501 and Proteus vulgaris NCIM 2813 were evaluated by a microdilution method. Group-based quantitative structure activity relationships (GQSAR) for all antibacterial activities were developed. The statistical measures namely r2 (0.66–0.85), r2 adj (0.63–0.84), q2 (0.54–0.79) and F-ratio (11.63–34.17) were found to be satisfactory. All of the test and training set compounds were found to be within a 99% confidence level. Descriptors pertaining to hydrophobicity, topology and electrostatic interactions of the substitutions were found to contribute to their activities.

Graphical abstract: Expeditious synthesis, antibacterial activity evaluation and GQSAR studies of 3-bisoxindoles, 2-oxindolyl-2-hydroxyindan-1,3-diones and 2-oxindolyl-2-hydroxyacenaphthylen-1-ones

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Supplementary files

Article information


Submitted
01 Dec 2011
Accepted
04 Nov 2012
First published
22 Nov 2012

RSC Adv., 2013,3, 496-507
Article type
Paper

Expeditious synthesis, antibacterial activity evaluation and GQSAR studies of 3-bisoxindoles, 2-oxindolyl-2-hydroxyindan-1,3-diones and 2-oxindolyl-2-hydroxyacenaphthylen-1-ones

N. V. Lakshmi, P. M. Sivakumar, D. Muralidharan, M. Doble and P. T. Perumal, RSC Adv., 2013, 3, 496
DOI: 10.1039/C2RA01215D

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