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.

Abbasi, Muhammad Athar; Irshad, Misbah; Aziz-ur-Rehman; Siddiqui, Sabahat Zahra; Nazir, Majid; Shah, Syed Adnan Ali; Shahid, Muhammad

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.

ACETAMIDE; ANTIFUNGAL agents; ANTIBACTERIAL agents; LITHIUM hydride; ELECTROPHILES; ANILINE

Pakistan Journal of Pharmaceutical Sciences, 2020, Vol 33, Issue 5, p2161

1011-601X

Academic Journal

10.36721/PJPS.2020.33.5.REG.2161-2170.1