SYNTHESIS OF SOME NEW N-SUBSTITUTED-N-(2,3-DIHYDRO-[1,4]-BENZODIOXIN-6-YL)-4-ACETAMIDOBENZENESULFONAMIDES AS VALUABLE ANTIBACTERIAL AGENTS

^#E-mail: [email protected]; [email protected]

*Department of Chemistry, Government College University, Lahore, 54000, Pakistan;
**Department of Pharmacy, the Islamia University of Bahawalpur, Bahawalpur, 63100, Pakistan;
***Faculty of Pharmacy, University Technology MARA, Puncak Alam Campus, 42300 Bandar Puncak Alam, Selangor Darul Ehsan, Malaysia;
****Atta-ur-Rahman Institute for Natural Products Discovery (AuRIns), Level 9, FF3, University Teknologi MARA, Puncak Alam Campus, 42300 Bandar Puncak Alam, Selangor Darul Ehsan, Malaysia

Received 09.06.2015; in final form, 12.07.2015

The aim of the research was to investigate the anti-bacterial potential of some N-substituted sulfonamides bearing benzodioxane moiety. The synthesis was started by reaction of N-2,3-dihydrobenzo[1,4]-dioxin-6-amine with 4-acetamidobenzene-1-sulfonyl chloride in the presence of 10% aqueous Na₂CO₃ solution to yield N-(2,3-dihydrobenzo[1,4]-dioxin-6-yl)-4-acetamidobenzenesulfonamide, which was further reacted with alkyl/aralkyl halides in DMF and lithium hydride as a base to afford N-substituted-N-(2,3-dihydro-[1,4]-benzodioxin-6-yl)-4-acetamidobenzenesulfonamides. All the synthesized compounds were characterized by spectral data (IR, ¹H NMR, EI-MS, and HR-MS). The compounds were tested for anti-bacterial activity and most of them exhibited potent therapeutic potential against various gram-negative and gram-positive strains.

Keywords: N-(2,3-dihydrobenzo[1,4]-dioxin-6-yl)-4-acetamidobenzenesulfonamide, alkyl/aralkyl halides, spectral analysis, antibacterial activity.

Биоорг. химия 2016, 42 (2): 221-232