Synthesis, antibacterial and lipoxygenase inhibition studies of N-(Alkyl/aralkyl)-N-(2,3-dihydro-1,4-benzodioxin-6-yl)-4-methylbenzenesulfonamides

• Main Authors: Abbasi, M.A (Author), Ahmad, I. (Author), Aziz-ur-rehman (Author), Malik, R. (Author), Nazir, S. (Author), Shah, S.A (Author), Sheeza, A. (Author), Siddiqui, S.Z (Author)
• Format: Article
• Language: English
• Published: Turkish Pharmacists Association 2017
• Subjects: 1H-NMR; 2; 3-dihydro-1; 4-benzodioxin-6-amine; antibacterial activity; Antibacterial potential; antiinfective agent; Article; Bacillus subtilis; ciprofloxacin; controlled study; drug determination; drug effect; drug structure; drug synthesis; enzyme inhibition; Escherichia coli; growth inhibition; infrared radiation; lipoxygenase; Lipoxygenase; mass spectrometry; minimum inhibitory concentration; n (2 bromoethyl) n (2,3 dihydro 1,4 benzodioxin 6 yl) 4 methylbenzenesulfonamide; n (2 chlorobenzyl) n (2,3 dihydro 1,4 benzodioxin 6 yl) 4 methylbenzenesulfonamide; n (2,3 dihydro 1,4 benzodioxin 6 yl) 4 methylbenzenesulfonamide; n (2,3 dihydro 1,4 benzodioxin 6 yl) n (2 phenethyl) 4 methylbenzenesulfonamide; n (2,3 dihydro 1,4 benzodioxin 6 yl) n (3 phenylpropyl) 4 methylbenzenesulfonamide; n (4 chlorobenzyl) n (2,3 dihydro 1,4 benzodioxin 6 yl) 4 methylbenzenesulfonamide; n (alkyl aralkyl) n (2,3 dihydro 1,4 benzodioxin 6 yl) 4 methylbenzenesulfonamide; nonhuman; proton nuclear magnetic resonance; Salmonella enterica serovar Typhi; unclassified drug
• Online Access: View Fulltext in Publisher; View in Scopus
• ISBN: 1304530X (ISSN)
• ISSN: 1304530X (ISSN)
• DOI: 10.4274/tjps.84756

Objectives: The present research work was aimed to synthesize some new sulfonamides bearing 1,4-benzodioxin ring, which might have suitable antibacterial potential and can be used as possible therapeutic agents for inflammatory ailments. Materials and Methods: The synthesis was accomplished by the reaction of 2,3-dihydro-1,4-benzodioxin-6-amine (1) with 4-methylbenzenesulfonyl chloride (2) using 10% aqueous Na2CO3 to afford N-(2,3-dihydro-1,4-benzodioxin-6-yl)-4-methylbenzenesulfonamide (3). Further the parent molecule 3 was reacted with different alkyl/aralkyl halides (4a-e) to achieve N-(alkyl/aralkyl)-N-(2,3-dihydro-1,4-benzodioxin-6-yl)-4-methylbenzenesulfonamides (5a-e), using polar aprotic solvent; N,N-dimethylformamide (DMF) and catalytic amount of lithium hydride as base. The characterization of synthesized compounds was conducted by contemporary spectral techniques e.g., IR, 1H-NMR and EI-MS. Then these molecules were subjected to screening against various bacterial strains and their inhibitory potential against Lipoxygenase was also ascertained. Results: The screening results against various Gram-positive and Gram-negative bacterial strains revealed that N-(2,3-dihydro-1,4-benzodioxin-6-yl)-4-methylbenzenesulfonamide (3), N-(2-bromoethyl)-N-(2,3-dihydro-1,4-benzodioxin-6-yl)-4-methylbenzenesulfonamide (5a) and N-(2-phenethyl)-N-(2,3-dihydro-1,4-benzodioxin-6-yl)-4-methylbenzenesulfonamide (5b) showed good inhibitory activity as compared to standard Ciprofloxacin. Moreover, N-(3-phenylpropyl)-N-(2,3-dihydro-1,4-benzodioxin-6-yl)-4-methylbenzenesulfonamide (5c) and N-(4-chlorobenzyl)-N-(2,3-dihydro-1,4-benzodioxin-6-yl)-4-methylbenzenesulfon-amide (5e) displayed decent inhibition against lipoxygenase enzyme relative to standard Baicalein. Conclusion: On the basis of results obtained it can be concluded that the synthesized sulfonamides may provide an overall indispensable basis to introduce new drug candidates for the cure of inflammatory and other associated diseases. © Turk J Pharm Sci, Published by Galenos Publishing House.