Abstract
A new series of chlorosulfonylcarbamate and urea heterocyclic benzenesulfonamides derivatives were synthesized to study the biological activities, via the reaction of chlorosulfonylisocyanate (CSI) on active heterocyclic N-ethyl-N-methylbenzenesulfonamide derivatives containing hydroxy (OH) and/or amino (NH and NH2) groups. The products were obtained in one pot short reaction times, high yields and high purities. The structures of the new prepared products were identified by elemental analysis, IR, 1H NMR, 13C NMR and MS spectral data. All the prepared products were investigated as in-vitro antitumor activity (CACO, A549, HEP-2), as in-vitro antimicrobial agents (Gram + and Gram -), as antifungal and as anti-tuberculosis agents. The effect of addition of chlorosulfonylcarbamate Cl–SO2–NH–CO–O- and urea Cl–SO2–NH–CO–N- groups was studied. The molecular docking studies of the prepared compounds using the Molecular Operating Environment (MOE) demonstrate that some new compounds are good inhibitors of dihydrofolate reductase (DHFR).
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•Synthesis of novel heterocyclic chlorosulfonylcarbamate and urea benzenesulfonamides derivatives.•The effect of addition of chlorosulfonylcarbamate and urea groups was studied.•The structures of the all new prepared compounds were identified by elemental analysis and spectral data.•All the compounds were in-vitro investigated as antitumor, antimicrobial and anti-tuberculosis.•Some compounds exhibited excellent anticancer and antimicrobial results.•Molecular docking studies confirm binding site of active compounds with DHFR enzyme.