Synthesis, molecular docking and antibacterial evaluation of 2-(4-(4-aminophenylsulfonyl)phenylamino)-3-(thiophen-2-ylthio)naphthalene-1,4-dione derivatives

Abstract

A new series of 2-(4-(4-aminophenylsulfonyl)phenylamino)-3-(thiophen-2-ylthio)naphthalene-1,4-dione derivatives (3a-3n) were synthesized and characterized by spectral techniques. To understand the interaction of binding sites with bacterial protein receptor, the docking study was performed by the GLIDE program and compound N-(4-(4-(1,4-dioxo-3-(thiophen-2-ylthio)-1,4-dihydronaphthalen-2-ylamino)phenylsulfonyl)phenyl)-3-methylbenzamide (3b) exhibited good glide and E model scores of ‒5.89 and ‒94.90, respectively. Moreover among all the molecules studied including the standards used, namely Sparfloxacin (4.8 µg/mL) and Norfloxacin (no inhibition observed) for their antibacterial property, compound N-(4-(4-(1,4-dioxo-3-(thiophen-2-ylthio)-1,4-dihydronaphthalen-2-ylamino)phenylsulfonyl)phenyl)-4-nitrobenzamide (3e) exhibited the lowest minimum inhibitory concentration (MIC) value of 1.3 µg/mL against Proteus vulgaris.

Graphical abstract

Keywords

MIC / 2-thiophene thiol / water as solvent / acid chlorides / sulfone

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Acknowledgements

The authors thank the Management and the authorities of Karunya University, Coimbatore, for their kind support, constant encouragement and also for providing KSJF fellowship to PR. Our thanks are also extended to SAIF, IIT, Madras, India and SAIF, IISC, Bangalore, India for NMR and Mass spectral analysis.

RIGHTS & PERMISSIONS

2014 Higher Education Press and Springer-Verlag Berlin Heidelberg