Synthesis, Characterization, Antibacterial, α-Glucosidase Inhibition and Hemolytic Studies on Some New N-(2,3- Dimethylphenyl)benzenesulfonamide Derivatives

Muhammad A Abbasi,Kaniz Rubab,Shahid Rasool,Aziz-Ur Rehman,Irshad Ahmad,Muhammad Shahid,Ghulam Hussain,Muhammad Ashraf,Mudassar Islam,Syed Adnan Ali Shah

doi:10.4314/tjpr.v15i3.22

Abstract

Purpose: To synthesize a series of new N-(2,3-dimethylphenyl)benzenesulfonamide derivatives with pharmacological analysis. Methods: N-(2,3-Dimethylphenyl)benzenesulfonamide (3) was synthesized by the reaction between 2,3-dimethylaniline (1) and benzenesulfonyl chloride (2) in aqueous basic medium. Compound 3 was further treated with various alkyl/aralakyl halides (4a-m) to yield new compounds, 5a-m, in a weak basic aprotic polar organic medium. The proposed structures of synthesized compounds were confirmed using proton-nuclear magnetic resonance (1H-NMR), infra red spectroscopy (IR) and electron impact mass spectrometry (EIMS). The synthesized compounds were screened for in vitro antibacterial, antienzymatic and hemolytic activities using standard procedures. Results: All the synthesized compounds showed moderate to high activity against Gram-positive and Gram-negative bacterial strains. The molecules 5g and 5j exhibited good inhibition of α-glucosidase enzyme with half-maximal inhibitory concentration (IC 50 ) of 59.53 ± 0.01 and 55.31 ± 0.01 μmoles/L, respectively, relative to acarbose with IC 50 of 38.25 ± 0.12 μmoles/L. All the compounds exhibited cytotoxicity levels ranging from 27.20 ± 0.24 to 5.20 ± 0.41 %, relative to Triton X-100. Conclusion: Compound 5f is the most potent antibacterial while 5j is the best α-glucosidase inhibitor; 5e showed the least cytotoxicity. Keywords: 2,3-Dimethylaniline, Antibacterial activity, Anti-enzymatic activity, α-Glucosidase inhibitor, Hemolytic activity, Sulfonamides

Highlights

Sulfonamides exhibit numerous pharmacological activities [1,2,3] and sulfonamide antibiotics are among the most common instigators of allergic or hypersensitivity reactions [4,5,6]. α-Glucosidase (α-D-glucosideglucohydrolase, EC3.2.1.20)hydrolyzes the 1,4-glycosidic linkage from the non-reducing end of the α-glucosides [7,8,9].Its inhibitors retard the liberation of D-glucose resulting in delay glucose absorption [10]
Our group has synthesized many antibacterial and anti-enzymatic potent molecules [13,14,15,16] and a series of new compounds was synthesized in the present study to explore their pharmacological behavior
FTIR spectra were recorded on MIDAC M 2000 spectrometer. 1H-NMR spectra were recorded in CDCl3 on Bruker (400 MHz)

Summary

Introduction

Sulfonamides exhibit numerous pharmacological activities [1,2,3] and sulfonamide antibiotics are among the most common instigators of allergic or hypersensitivity reactions [4,5,6]. α-Glucosidase (α-D-glucosideglucohydrolase, EC3.2.1.20)hydrolyzes the 1,4-glycosidic linkage from the non-reducing end of the α-glucosides [7,8,9].Its inhibitors retard the liberation of D-glucose resulting in delay glucose absorption [10]. Sulfonamides exhibit numerous pharmacological activities [1,2,3] and sulfonamide antibiotics are among the most common instigators of allergic or hypersensitivity reactions [4,5,6]. Our group has synthesized many antibacterial and anti-enzymatic potent molecules [13,14,15,16] and a series of new compounds was synthesized in the present study to explore their pharmacological behavior. The chemicals solvents were of commercial grade and were used without purification. Reaction progress and product purity was monitored by pre-coated TLC silica gel G-25UV254 plates with different solvent systems using ethyl acetate and n-hexane. FTIR spectra were recorded on MIDAC M 2000 spectrometer. 1H-NMR spectra were recorded in CDCl3 on Bruker (400 MHz). Mass spectra (EIMS) were measured on Finnigan MAT-312 instruments

Methods

Results

Conclusion