Synthesis, characterization, cytotoxicity evaluation and physicochemical properties of some novel N4-substituted aminobenzenesulfonamides

Abstract

Several N⁴-substituted aminobenzenesulfonamides derivatives have been synthesized and structural analyses have been carried out using FT-IR, UV-Vis, ¹H and ¹³C NMR, LC-MS-MS and elemental analyses. Photoluminescence and physicochemical properties have also been conducted. Two 4-aminobenzenesulfonamides have been treated with 2-bromopropionyl bromide in pyridine to give their respective bromo substituted aminobenzenesulfonamides as intermediates. Subsequent reactions with morpholino-, thiomorpholino- and piperazine amines have yielded novel aminobenzenesulfonamide derivatives. As it is well known that CA IX and CA XII enzymes play an active role in attacking various cancerous conditions, studies presented in this study target these enzymes with in vitro cytotoxicity studies being performed on the compounds synthesized. The target compounds have been found to be active against some cancerous cells, with mimimal effects on normal cells. The physicochemical data reveal interesting synergistic effects controlling cytotoxicities, where the lipophilicity and polarity combinations play important roles on the eventual observed cytotoxicities. Further, the electronegativity and availability of the electrons of the heteroatoms of the synthesized compounds appear to have an effect on cancer cell cytotoxicities.