Synthesis, Spectral Characterization, Docking Studies and QSAR Screening of 4-amino-benzenesulfonamides/N-acetyl 4-amino-benzenesulfonamide Derivatives as Antimicrobial Agents
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Keywords

 Sulfonamide, in-silico studies, statistics, quantitative structure activity relationship.

How to Cite

Ajeet, Laxmi Tripathi, & Arvind Kumar. (2014). Synthesis, Spectral Characterization, Docking Studies and QSAR Screening of 4-amino-benzenesulfonamides/N-acetyl 4-amino-benzenesulfonamide Derivatives as Antimicrobial Agents. Journal of Pharmacy and Nutrition Sciences, 4(2), 135–153. https://doi.org/10.6000/1927-5951.2014.04.02.10

Abstract

A series of substituted 4-amino-benzenesulfonamides / N-acetyl-4-amino-benzenesulfonamide were designed & synthesized keeping in view the structural requirements of pharmacophore and were evaluated for in-silicoantimicrobial activity. For establishing the structure, spectral characterization like FT-IR, 1H NMR, GC-MS and elemental analysis (CHNS) has been performed. The antimicrobial activity of the titled compounds was assessed using in-silico studies (QSAR screening and Docking). It was carried out for the prediction of pharmacokinetic properties and to study the binding properties of drugs with molecular targets. Titled compounds exhibited good binding properties with molecular target. It could be concluded that molecular target responsible for the antimicrobial activity of substituted 4-amino-benzenesulfonamides / N-acetyl-4-amino-benzenesulfonamides may be pseudomonas aeruginosa exotoxin A.

https://doi.org/10.6000/1927-5951.2014.04.02.10
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References

Jones ME, Blosser-Middleton RS, Thornsberry C, Karlowsky JA, Sahm DF. The activity of levofloxacin and other antimicrobials against clinical isolates of Streptococcus pneumoniae collected worldwide during 1999-2002. Diagn Microbiol Infect Dis 2003; 47: 579-86. http://dx.doi.org/10.1016/S0732-8893(03)00140-8

Fouda SI, Kadry AA, Shibl AM. Beta-lactam and macrolide resistance and serotype distribution among Streptococcus pneumoniae isolates from Saudi Arabia. J Chemother 2004; 16: 517-23. http://dx.doi.org/10.1179/joc.2004.16.6.517

Jenkins SG, Farrell DJ, Patel M, Lavin BS. Trends in antibacterial resistance among Streptococcus pneumonia isolated in the USA, 2000-2003: PROTEK US years 1-3. J Infect 2005; 51: 355-63. http://dx.doi.org/10.1016/j.jinf.2005.04.015

Kaye KS, Engemann JJ, Fraimow HS, Abrutyn E. Pathogens resistant to antimicrobial agents:epidemiology, molecular mechanisms, and clinical management. Infect Dis Clin North Am 2004; 18: 467-11. http://dx.doi.org/10.1016/j.idc.2004.04.003

Cuellar-Rodríguez J, et al. Vancomycin-resistant enterococci, México City. Emerg Infect Dis 2007; 13: 798-99. http://dx.doi.org/10.3201/eid1305.061421

Tenover FC. Mechanisms of antimicrobial resistance in bacteria. Am J Med 2006; 119: S3-S10.

Murthy A, De Angelis G, Pittet D, Schrenzel J, Uckay I, Harbarth S. Cost-effectiveness of universal MRSA screening on admission to surgery. Clin Microbiol Infect 2010; 16: 1747- 53. http://dx.doi.org/10.1111/j.1469-0691.2010.03220.x

Hong YL, Hossler PA, Calhoun DH, Meshnick SR. Inhibition of recombinant Pneumocystis carinii dihydropteroate synthetase by sulfa drugs. Antimicrob Agents Chemother 1995; 39: 1756-63. http://dx.doi.org/10.1128/AAC.39.8.1756

Furniss BS, Hannaford AJ, Smith PWG, Tatchell AR. In: Vogel’s Textook of Practical Organic Chemistry. Prentice Hall, New York 1989.

Naama H, Meir B, Bogdan W, Richard HF, Boris Y. Syntheses and evaluation of anticonvulsant profile and teratogenicity of novel amide derivatives of branched aliphatic carboxylic acids with 4-aminobenzensulfonamide. J Med Chem 2010; 53: 4177-86. http://dx.doi.org/10.1021/jm100170w

Ajeet. Chlorambucil derivatives as antineoplastic agent: insilico designing and docking. Int J Cur Pharm Res 2011; 3(4): 81-84.

Ajeet. Trans-disciplinary receptor binding of acyclovir to human phenylalanine hydroxylase: docking approach. Int J Pharm Pharm Sci 2012; 4(Suppl 3): 182-84.

Ajeet. In silico designing and characterization of Amiloride derivatives as ion channel modulator. Med Chem Res 2013; 22(2): 1004-10. http://dx.doi.org/10.1007/s00044-012-0096-9

Ajeet, Kumar P, Tripathi L. Virtual Screening Tool Based Designing and Evaluation of Novel Sulfonamide Derivatives as Anticonvulsant Agent – A Pharmacophoric Approach. Int J Pharm Phytopharmacol Res 2012; 2(3): 202-08.

Ajeet, Tripathi L, Kumar P. Designing of Novel 6(H)-1,3,4- Thiadiazine Derivatives as MMP12 Inhibitors: A MLR and Docking Approach. Am J Pharmacol Sci 2013; 1(2): 29-34. http://dx.doi.org/10.12691/ajps-1-2-3

Ajeet, Kumar A. Designing of Hybrid form of Benzothiazolequinazoline as GABA-A Inhibitor with Anticonvulsant Profile: An in-silico Approach. Am J Pharmacol Sci 2013; 1(6): 116- 20. http://dx.doi.org/10.12691/ajps-1-6-2

Verma RP, Hansch C. QSAR modeling of taxane analogues against colon cancer. Eur J Med Chem 2010; 45: 1470-77. http://dx.doi.org/10.1016/j.ejmech.2009.12.054

Verma RP, Hansch C. Matrix metalloproteinases (MMPs): Chemical–biological functions and (Q)SARs. Bioorg Med Chem 2007; 15: 2223-68. http://dx.doi.org/10.1016/j.bmc.2007.01.011

Ajeet. QSAR modeling of recombinant human stromelysin inhibitors– MLR approach. Int J Adv Pharm Biol Sci 2012; 2(2): 171-75.

Ajeet. Prediction of novel arylpiperazinyls (pyrrolidin-2-one derivatives) as antiarrhythmic agents – QSAR model development. Int J Pharmac Arch 2012; 1(1): 12-20.

Ajeet. Prediction of 44 novel Succinyl Hydroxamates and their carboxylic analogues against MMP2– QSAR modeling. Novel Sci Int J Pharmac Sci 2012; 1(11-12): 713-17.

Ajeet. Development of QSAR model for studying sulfonamide derivatives against carbonic anhydrase using multiple linear regression with McGowan volume and AlogP as molecular descriptors. J Harmo Res Pharm 2013; 2(1): 45-53.

Ajeet. QSAR modeling of beta-lactam antibiotic cephalosporin against transpeptidase using MLR method. Eur J Bioinformat 2013; 1: 1-7.

Ajeet, Kumar P, Tripathi L. QSAR Model Development for Studying Sulfonamide Derivatives as Carbonic Anhydrase Inhibitors- A MLR Approach. Int J Pharm Res Tech 2013; 5(1): 74-81.

Ajeet. QSAR Study of Methionine Aminopeptidase Inhibitors as Anti-cancer Agents Using MLR Approach. Am J Pharmacol Sci 2013; 1(5): 80-83.

Ajeet. Triterpene acid (3?-hydroxyurs-12-en-28-oic acid) against human lung cancer A-549 cells- multiple linear regression based QSAR modeling. Eur J Bioinformat 2013; 1: 8-14.

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Copyright (c) 2014 Ajeet, Laxmi Tripathi , Arvind Kumar