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. 2010 Dec;45(12):5985-97.
doi: 10.1016/j.ejmech.2010.09.065. Epub 2010 Oct 7.

4-[1-(Substituted aryl/alkyl carbonyl)-benzoimidazol-2-yl]-benzenesulfonic acids: synthesis, antimicrobial activity, QSAR studies, and antiviral evaluation

Snehlata Yadav  1 , Pradeep Kumar, Erik De Clercq, Jan Balzarini, Christophe Pannecouque, Sharwan Kumar Dewan, Balasubramanian Narasimhan
Affiliations

4-[1-(Substituted aryl/alkyl carbonyl)-benzoimidazol-2-yl]-benzenesulfonic acids: synthesis, antimicrobial activity, QSAR studies, and antiviral evaluation

Snehlata Yadav et al. Eur J Med Chem. 2010 Dec.

Abstract

A series of 4-[1-(substituted aryl/alkyl carbonyl)-benzoimidazol-2-yl]-benzene sulphonic acids (1-20) was synthesized and evaluated, in vitro, for their antimicrobial activity and the results indicated that compounds 4-[1-(4-Nitrobenzoyl)-1H-benzoimidazol-2-yl]-benzenesulfonic acid (9) and 4-(1-octadec-9-enoyl-1H-benzoimidazol-2-yl)-benzenesulfonic acid (18) were found to be the most active ones. QSAR investigations indicated that the multi-target QSAR model was effective in describing the antimicrobial activity over the one-target QSAR models. Further the mt-QSAR model indicated the importance of the topological parameter, Balaban index (J) followed by the electronic parameter, LUMO and topological parameter, valence second order molecular connectivity index (2χv) in describing the antimicrobial activity of synthesized compounds (1-20).

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Figures

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Graphical abstract
Scheme 1
Scheme 1
Scheme for the synthesis of 4-[1-(substituted aryl/alkyl)-benzoimidazol-2-yl]-benzenesulfonic acids.
Fig. 1
Fig. 1
Plot of predicted pMICsa against the experimental pMICsa for the MLR model developed by Eq. (3).
Fig. 2
Fig. 2
Plot of residual pMICsa against the experimental pMICsa by Eq. (3).
Fig. 3
Fig. 3
Plot of predicted pMICam against the experimental pMICam values for the MLR model developed by Eq. (13).
Fig. 4
Fig. 4
Plot of predicted pMICam values against the experimental pMICam values for the MLR model developed by Eq. (13).
None
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