Synthesis, antitumor activity and molecular docking study of novel Sulfonamide-Schiff's bases, thiazolidinones, benzothiazinones and their C-nucleoside derivatives

A series of sulfapyridine-polyhydroxyalkylidene (or arylidene)-imino derivatives (Schiff's bases) 2a–c and 4a–e were prepared by condensation of 4-amino-N-pyridin-2-ylbenzenesulfonamide (1) with different monosaccharides or with aromatic aldehydes. Treatment of 2a–c with thioglycolic acid led to the formation of the C-nucleosides (3a–c), while treatment of 4a–e with thioglycolic and/or thiosalicylic acids afforded the corresponding 2-arylthiazolidin-4-one or 2-arylbenzothiazin-4-one derivatives 5a–e and/or 6a–e, respectively. Some representative examples of the newly prepared compounds showed considerable cytotoxic effect against breast carcinoma cell line MCF7 and cervix carcinoma cell line HELA in comparison with 5-flurouracil and doxorubicin. AutoDock molecular docking into PTK has been done for lead optimization of the compounds in study as potential PTK inhibitors.

Graphical abstractSome Schiff's bases, C-nucleosides, thiazolidin-4-ones and benzothiazin-4-ones were prepared and their antitumor activity was evaluated in-vitro and compared to molecular docking data.Figure optionsDownload full-size imageDownload as PowerPoint slide