Synthesis of promising antibacterial and antifungal agents: 2-[[(4-Chlorophenyl)sulfonyl](2,3-dihydro-1,4-benzodioxin-6-yl)amino]-N(un/substituted-phenyl)acetamides

• Published in: Pakistan Journal of Pharmaceutical Sciences
• Main Author: Abbasi M.A.; Irshad M.; Aziz-Ur-Rehman; Siddiqui S.Z.; Nazir M.; Ali Shah S.A.; Shahid M.
• Format: Article
• Language: English
• Published: Pakistan Journal of Pharmaceutical Sciences 2020
• Online Access: https://www.scopus.com/inward/record.uri?eid=2-s2.0-85091220218&doi=10.36721%2fPJPS.2020.33.5.REG.2161-2170.1&partnerID=40&md5=f1a3b1fca03fa9ea9de6769267c5acba

In the presented work, 2,3-dihydro-1,4-benzodioxin-6-amine (1) was reacted with 4-chlorobenzenesulfonyl chloride (2) in presence of aqueous basic aqueous medium to obtain 4-chloro-N-(2,3-dihydro-1,4-benzodioxin-6-yl)benzenesulfonamide (3). In parallel, various un/substituted anilines (4a-l) were treated with bromoacetyl bromide (5) in basified aqueous medium to obtain corresponding 2-bromo-N-(un/substituted)phenylacetamides (6a-l) as electrophiles. Then the compound 3 was finally reacted with these electrophiles, 6a-l, in dimethylformamide (DMF) as solvent and lithium hydride as base and activator to synthesize a variety of 2-[[(4-chlorophenyl)sulfonyl](2,3-dihydro-1,4-benzodioxin-6-yl)amino]-N-(un/substituted)phenylacetamides (7a-l). The synthesized compounds were corroborated by IR, 1H-NMR and EI-MS spectral data for structural confirmations. These molecules were then evaluated for their antimicrobial and antifungal activities along with their %age hemolytic activity. Some compounds were found to have suitable antibacterial and antifungal potential, especially the compound 2-[[(4-chlorophenyl)sulfonyl](2,3-dihydro-1,4-benzodioxin-6-yl)amino]-N-(3,5-dimethylphenyl)acetamide (7l) exhibited good antimicrobial potential with low value of % hemolytic activity. © 2020 Pakistan Journal of Pharmaceutical Sciences. All rights reserved.