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 2019, Vol.41 (4), p.685-685
• Main Authors: Muhammad Athar Abbasi, Muhammad Athar Abbasi, Wajiha Khan, Wajiha Khan, Aziz ur Rehman, Aziz ur Rehman, Sabahat Zahra Siddiqui, Sabahat Zahra Siddiqui, Ghulam Hussain, Ghulam Hussain, Syed Adnan Ali Shah, Syed Adnan Ali Shah, Muhammad Shahid and Khalid Mohammed Khan, Muhammad Shahid and Khalid Mohammed Khan
• Format: Article
• Language: English
• ISSN: 0253-5106
• DOI: 10.52568/000773/JCSP/41.04.2019

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.