title: Synthesis, biological screening and molecular docking studies of some ethylated sulfonamides having 1,4-Benzodioxane moiety.
abstract: The presented study comprises the synthesis of a new series of ethylated sulfonamides in which 1,4-benzodioxane moiety has been incorporated. The reaction of 1,4-benzodioxane-6-amine (1) with ethane sulfonyl chloride (2) yielded N-(2,3-dihydrobenzo[1,4]dioxin-6-yl)ethanesulfonamide (3), which further on treatment with various alkyl/aralkyl halides, 4a-r, in N,Nꞌ-dimethylformamide (DMF) and in the presence of lithium hydride (LiH) acting as a weak base and catalyst; yielded derivatives of N-alkyl/aralkyl substituted N-(2,3-dihydrobenzo[1,4]dioxin-6-yl)ethanesulfonamides (5a-r). The characterization of these derivatives was carried out by different spectroscopic techniques like infra red, proton-NMR and mass spectrometry; then screened against various enzymes i.e. acetylcholinesterase, butyrylcholinesterase, lipoxygenase and α-glucosidase enzymes and five different bacterial strains. The synthesized compounds were found to be good inhibitors of lipoxygenase but moderate inhibitors of AChE, BChE and α-glucosidase; whereas compounds 3, 5a, 5f, 5n and 5r were found good antibacterial compounds. The interaction between inhibitors and target enzymes (cholinestrases and lipoxygenase) was computationally observed which correlated with the experimental results.
authors.affiliation: Division of Science and Technology, University of Education, Township Campus, Lahore, Pakistan.
authors.forename: Misbah
authors.initials: M
authors.lastname: Irshad
authors.affiliation: Department of Chemistry, Government College University, Lahore, Pakistan.
authors.forename: Muhammad Athar
authors.initials: MA
authors.lastname: Abbasi
authors.affiliation: Department of Chemistry, Government College University, Lahore, Pakistan.
authors.forename: Azizur Rehman
authors.initials: AR
authors.lastname: Rehman
authors.affiliation: Department of Chemistry, Government College University, Lahore, Pakistan.
authors.forename: Sabahat Zahra
authors.initials: SZ
authors.lastname: Siddiqui
authors.affiliation: HEJ Research Institute of Chemistry, International Center for Chemical and Biological Sciences, University of Karachi, Karachi, Pakistan.
authors.forename: Muhammad Shaiq
authors.initials: MS
authors.lastname: Ali
authors.affiliation: Department of Chemistry, The Islamia University of Bahawalpur, Bahawalpur, Pakistan.
authors.forename: Muhammad
authors.initials: M
authors.lastname: Ashraf
authors.affiliation: Department of Chemistry, The Islamia University of Bahawalpur, Bahawalpur, Pakistan.
authors.forename: Tayaba
authors.initials: T
authors.lastname: Ismail
authors.affiliation: Department of Pharmacy, The Islamia University of Bahawalpur, Bahawalpur, Pakistan.
authors.forename: Irshad
authors.initials: I
authors.lastname: Ahmad
authors.affiliation: Department of Pharmacy, The Islamia University of Bahawalpur, Bahawalpur, Pakistan.
authors.forename: Sidra
authors.initials: S
authors.lastname: Hassan
authors.affiliation: Department of Biochemistry, Abdul Wali Khan University Mardan, Pakistan.
authors.forename: Muhammad Arif
authors.initials: MA
authors.lastname: Lodhi
authors.affiliation: Department of Biochemistry, Abdul Wali Khan University Mardan, Pakistan.
authors.forename: Syed Babar
authors.initials: SB
authors.lastname: Jamal
mesh_terms: D000478:Alkylation; D000900:Anti-Bacterial Agents / Q000138:chemical synthesis* / Q000494:pharmacology*; D001419:Bacteria / Q000187:drug effects / Q000254:growth & development; D002800:Cholinesterase Inhibitors / Q000138:chemical synthesis / Q000494:pharmacology; D004146:Dioxanes / Q000138:chemical synthesis* / Q000494:pharmacology*; D004791:Enzyme Inhibitors / Q000138:chemical synthesis* / Q000494:pharmacology*; D065089:Glycoside Hydrolase Inhibitors / Q000138:chemical synthesis / Q000494:pharmacology; D016859:Lipoxygenase Inhibitors / Q000138:chemical synthesis / Q000494:pharmacology; D013058:Mass Spectrometry; D008826:Microbial Sensitivity Tests; D062105:Molecular Docking Simulation; D015394:Molecular Structure; D066244:Proton Magnetic Resonance Spectroscopy; D013055:Spectrophotometry, Infrared; D013329:Structure-Activity Relationship; D013449:Sulfonamides / Q000138:chemical synthesis* / Q000494:pharmacology*; D013678:Technology, Pharmaceutical / Q000379:methods
chemical_list: D000900:Anti-Bacterial Agents; D002800:Cholinesterase Inhibitors; D004146:Dioxanes; D004791:Enzyme Inhibitors; D065089:Glycoside Hydrolase Inhibitors; D016859:Lipoxygenase Inhibitors; D013449:Sulfonamides; C527681:1,4-benzodioxan