Linear synthesis of {4-[(2-Alkoxy/aralkyloxy-3,5-dichlorophenyl)sulfonyl]-1-piperazinyl}(2-furyl)methanones as possible therapeutic agents

• Published in: Journal of the Chemical Society of Pakistan
• Main Author: Abbasi M.A.; Khan W.; Aziz-Ur-Rehman; Siddiqui S.Z.; Hussain G.; Shah S.A.A.; Shahid M.; Khan K.M.
• Format: Article
• Language: English
• Published: Chemical Society of Pakistan 2019
• Online Access: https://www.scopus.com/inward/record.uri?eid=2-s2.0-85072195513&partnerID=40&md5=df9215a18337a7003bd72c985271f569

Summary: In the present work, a series of {4-[(2-alkyloxy/aralkyloxy-3,5-dichlorophenyl)sulfonyl]- 1-piperazinyl}(2-furyl)methanones was synthesized through a linear bi-step approach. The synthesis was initiated by the coupling of 2-furyl(1-piperazinyl)methanone (1) with 3,5-dichloro-2- hydroxybenzenesulfonyl chloride (2) under dynamic pH control in aqueous alkaline medium to form parent compound, {4-[(3,5-dichloro-2-hydroxyphenyl)sulfonyl]-1-piperazinyl}(2-furyl)methanone (3). Then, the O-substitution reaction on nucleophile 3 was carried out by treating it with different alkyl/aralkyl halides (4a-l) in the presence of lithium hydride (LiH) and N,N-dimethylformamide (DMF) to obtained the designed {4-[(2-alkoxy/aralkyloxy-3,5-dichlorophenyl)sulfonyl]-1- piperazinyl}(2-furyl)methanones (5a-l). These synthesized compounds were screened against α- glucosidase enzyme and some of them exhibited considerable inhibitory activity. Additionally, compounds were also evaluated for hemolytic and cytotoxic profile. © 2019 Chemical Society of Pakistan. All rights reserved.