Abstract
A novel series of sulfonamide derivatives 4–21 have been synthesized starting from the strategic starting material (E)-4-Chloro-N-(4-(1-(2-(2-cyanoacetyl)hydrazono)ethyl)phenyl) benzenesulfonamide 4. Two series of hydrazone 5–9, and pyridone 10–21 derivatives bearing a sulfonamide moiety were obtained. All the newly synthesized compounds were evaluated for their in vitro cytotoxic activity against human liver cancer cell line (HepG2). Compounds 4–6, 8, 9, 10–14 and 16–18 showed higher activity compared to doxorubicin as a positive control. The radiosensitizing ability of the most promising compounds 4, 10 and 12 was studied which showed an increase in the cell killing effect of γ-radiation after combination with these derivatives. The molecular design was performed to predict the binding mode of the most promising compounds 4, 10 and 12 with the active site of hCA IX, that showed appropriate fitting with the relevant amino acids in the binding pocket on the basis of standard bond lengths, angles, S score and E conformation data.
Novel series of sulfonamide derivatives bearing a biologically active hydrazone or pyridone moiety were synthesized. The most potent compounds in this study 4, 10 and 12 were evaluated for their radiosensitizing activity. [Display omitted]
•Novel sulfonamide derivatives bearing a hydrazone moiety were synthesized.•Novel sulfonamide derivatives bearing a pyridone moiety were synthesized.•In-vitro anticancer evaluation on HepG2 cell line.•Radiosensitizer evaluation for the most potent compounds.