Synthesis of some new N-(alkyl/aralkyl)-N-(4-methoxyphenethyl) benzenesulfonamides as antibacterial agents against Escherichia coli

• Published in: Pakistan Journal of Pharmaceutical Sciences
• Main Author: Abbasi M.A.; Fatima Z.; Aziz-Ur-Rehman; Siddiqui S.Z.; Ali Shah S.A.; Shahid M.; Fatima H.
• Format: Article
• Language: English
• Published: Pakistan Journal of Pharmaceutical Sciences 2019
• Online Access: https://www.scopus.com/inward/record.uri?eid=2-s2.0-85072317017&partnerID=40&md5=25c28cddf34cad060338b287dca5c3e1

The present study comprises the synthesis of a new series of benzenesulfonamides derived from N-sulfonation of 2-(4-methoxyphenyl)-1-ethanamine (1). The synthesis was initiated by the reaction of 2-(4-methoxyphenyl)-1-ethanamine (1) with benzenesulfonyl chloride (2), to yield N-(4-methoxyphenethyl)benzenesulfonamide (3). This parent molecule 3 was subsequently treated with various alkyl/aralkyl halides (4a-j) in N,N-dimethylformamide (DMF) and in the presence of a weak base lithium hydride (LiH) to obtain various N-(alkyl/aralkyl)-N-(4-methoxyphenethyl) benzenesulfonamides (5a-j). The characterization of these derivatives was carried out by spectroscopic techniques like IR, 1H-NMR, and 13C-NMR. Elemental analysis also supported this data. The biofilm inhibitory action of all the synthesized compounds was carried out on Escherichia coli and some of the compounds were identified to be very suitable inhibitors of this bacterial strain. Furthermore, the molecules were also tested for their cytotoxicity behavior to assess their utility as less cytotoxic therapeutic agents. © 2019 Pakistan Journal of Pharmaceutical Sciences. All rights reserved.