title: Synthesis, characterization, in vitro cytotoxicity and antimicrobial investigation and evaluation of physicochemical properties of novel 4-(2-methylacetamide)benzenesulfonamide derivatives.
abstract: In this study, several sulfonamide derivatives, 4-(2-methylacetylamino)benzenesulfonamides were synthesized. Chemical structures of the derivatives were characterized by1H NMR,13C NMR, LC-MS-MS, UV-Vis, FTIR, photoluminescence and elemental analysis. Sulfanilamide was reacted with 2-bromopropionyl bromide, in the presence of pyridine, to form bromo-substituted sulfonamide key intermediates, which were subsequently treated with secondary amines to obtain novel sulfonamide derivatives. All the synthesized compounds were evaluated for in vitro antimicrobial activities and cytotoxicity. Increases in ring size, and rings bearing a nitrogen heteroatom led to improvements in antimicrobial activities. As the presence of CA IX and CA XII enzymes have been implicated in some cancerous tumors, the studies presented herein focuses on targeting these enzymes. It was found that the synthesized derivatives had in vitro anti-cancer properties, where compounds (3-6) were found to be active against all cancerous cells, and no cytotoxic effects on normal cells were observed.
authors.affiliation: Department of Chemistry, Faculty of Science and Literature, Harran University, Sanliurfa 63190, Turkey.
authors.forename: Mustafa
authors.initials: M
authors.lastname: Durgun
authors.affiliation: Department of Medical Pharmacology, Faculty of Medicine, Harran University, Sanliurfa 63190, Turkey.
authors.forename: Hasan
authors.initials: H
authors.lastname: Turkmen
authors.affiliation: Department of Chemistry, Faculty of Science and Literature, Gaziantep University, Gaziantep 27310, Turkey. Electronic address: gzengin@gantep.edu.tr.
authors.forename: Gulay
authors.initials: G
authors.lastname: Zengin
authors.affiliation: Department of Chemistry, Faculty of Science and Literature, Gaziantep University, Gaziantep 27310, Turkey.
authors.forename: Huseyin
authors.initials: H
authors.lastname: Zengin
authors.affiliation: Department of Chemistry, Faculty of Science and Literature, Harran University, Sanliurfa 63190, Turkey.
authors.forename: Mehmet
authors.initials: M
authors.lastname: Koyunsever
authors.affiliation: Department of Biochemistry, Faculty of Medicine, Harran University, Sanliurfa 63190, Turkey.
authors.forename: Ismail
authors.initials: I
authors.lastname: Koyuncu
mesh_terms: D000081:Acetamides / Q000138:chemical synthesis / Q000737:chemistry / Q000494:pharmacology; D000890:Anti-Infective Agents / Q000138:chemical synthesis / Q000737:chemistry* / Q000494:pharmacology*; D000970:Antineoplastic Agents / Q000138:chemical synthesis / Q000737:chemistry* / Q000494:pharmacology*; D001419:Bacteria / Q000187:drug effects; D001424:Bacterial Infections / Q000188:drug therapy; D045744:Cell Line, Tumor; D004354:Drug Screening Assays, Antitumor; D005658:Fungi / Q000187:drug effects; D006801:Humans; D008826:Microbial Sensitivity Tests; D009181:Mycoses / Q000188:drug therapy; D009369:Neoplasms / Q000188:drug therapy; D013449:Sulfonamides / Q000138:chemical synthesis / Q000737:chemistry* / Q000494:pharmacology*; D000096926:Benzenesulfonamides
chemical_list: D000081:Acetamides; D000890:Anti-Infective Agents; D000970:Antineoplastic Agents; D013449:Sulfonamides; D000096926:Benzenesulfonamides
keywords: Antimicrobial activity; Cytotoxicity; Photoluminescence; Structure-activity relationships; Sulfonamide derivatives; Synthesis