Design, synthesis, characterization and computational docking studies of novel sulfonamide derivatives

Authors

  • Hira Saleem Department of Biosciences, COMSATS Institute of Information Technology, Islamabad, Pakistan
  • Arooma Maryam Department of Biosciences, COMSATS Institute of Information Technology, Islamabad, Pakistan
  • Saleem Ahmed Bokhari Department of Biosciences, COMSATS Institute of Information Technology, Islamabad, Pakistan
  • Ayesha Ashiq Department of Biosciences, COMSATS Institute of Information Technology, Islamabad, Pakistan
  • Sadaf Abdul Rauf Department of Computer Science, Fatima Jinnah Women University, The Mall, Rawalpindi
  • Rana Rehan Khalid Department of Biosciences, COMSATS Institute of Information Technology, Islamabad, Pakistan
  • Fahim Ashraf Qureshi Department of Biosciences, COMSATS Institute of Information Technology, Islamabad, Pakistan
  • Abdul Rauf Siddiqi Department of Biosciences, COMSATS Institute of Information Technology, Islamabad, Pakistan

DOI:

https://doi.org/10.17179/excli2017-886

Keywords:

sulfonamide, derivatives, synthesis, antimicrobial, activity, structure

Abstract

This study reports three novel sulfonamide derivatives 4-Chloro-N-[(4-methylphenyl) sulphonyl]-N-propyl benzamide (1A), N-(2-hydroxyphenyl)-4-methyl benzene sulfonamide (1B) and 4-methyl-N-(2-nitrophenyl) benzene sulfonamide (1C). The compounds were synthesised from starting material 4-methylbenzenesulfonyl chloride and their structure was studied through 1H-NMR and 13C-NMR spectra. Computational docking was performed to estimate their binding energy against bacterial p-amino benzoic acid (PABA) receptor, the dihydropteroate synthase (DHPS). The derivatives were tested in vitro for their antimicrobial activity against Gram+ and Gram- bacteria including E. coli, B. subtilis, B. licheniformis and B. linen. 1A was found active only against B. linen; 1B was effective against E. coli, B. subtilis and B. linen whereas 1C showed activity against E. coli, B. licheniformis and B. linen. 1C showed maximum activity with minimum inhibitory concentration (MIC) of 50, 100 and 150 µg/mL against E. coli, B. licheniformis and B. linen respectively. 1C exhibited maximum affinity to DHPS with binding free energy of -8.1 kcal/mol. It enriched in the top 0.5 % of a library of 7663 compounds, ranked in order of their binding affinity against DHPS. 1C was followed by 1B which showed a moderate to low level MIC of 100, 250 and 150 µg/mL against E. coli, B. subtilis and B. linen respectively, whereas 1A showed a moderate level MIC of 100 µg/mL but only against B. linen. These derivatives may thus serve as potential anti-bacterial alternatives against resistant pathogens.

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Published

2018-02-01

How to Cite

Saleem, H., Maryam, A., Bokhari, S. A., Ashiq, A., Rauf, S. A., Khalid, R. R., … Siddiqi, A. R. (2018). Design, synthesis, characterization and computational docking studies of novel sulfonamide derivatives. EXCLI Journal, 17, 169–180. https://doi.org/10.17179/excli2017-886

Issue

Vol. 17 (2018)

Section

Original articles

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