Design, synthesis, molecular docking and biological screening of N-ethyl-N-methylbenzenesulfonamide derivatives as effective antimicrobial and antiproliferative agents

Sulfonamides are the most famous agents, which have been utilized for preparation of effective antiproliferated agents. Therefore, this article describes the synthesis of new series of N-ethyl-N-methylbenzenesulfonamide derivatives having various biologically active moieties such as, thiazoles 3, 4, 11, 12, 14, 15, 21, 1,3,4-thiadiazine 6, imidazo[2,1-b]thiazole 8, 2-oxo-2H-chromene 17, and 3-oxo-3H-benzo[f] chromene 19, starting with 4-(2-bromoacetyl)-N-ethyl-N-methylbenzenesulfonamide (2), that was synthesized from the interaction of 4-acetyl-N-ethyl-N-methylbenzenesulfonamide (1) with bromine under stirring in dioxane/diethylether mixture. The newly structures were be proved via their elemental analysis and spectral data. However, they were also screened for their cytotoxic activity against two different human cell lines, alveolar adenocarcinoma carcinoma (lung) (A-549) and liver carcinoma (HepG2) and antimicrobial. Compound 8 having imidazo[2,1-b]thiazole moiety exhibited the most potent cytotoxic activity against (A-549) cell line (SI; 30.77). While, compound 11 having 2-cyanomethyl thiazole moiety showed significant cytotoxic activity against (HepG2) cell line (SI; 67.11). On the other hand, compound 9 having 4-chlorophenyl moiety exerted significant antimicrobial activity more than the reference drugs. Molecular Operating Environment (MOE) was performed for the synthesized compounds to study their mode of action as inhibitors against DHFR enzyme active sites. (C) 2019 Published by Elsevier B.V.