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.
Kamel
Mohsen M
MM
Medicinal Chemistry Department, National Research Centre, Dokki, Cairo, Egypt.
Ali
Hamed I
HI
Anwar
Manal M
MM
Mohamed
Neama A
NA
Soliman
Abdelmohsen M
AM
D000970:Antineoplastic Agents / Q000138:chemical synthesis / Q000737:chemistry / Q000378:metabolism / Q000494:pharmacology; D052160:Benzothiazoles / Q000737:chemistry*; D045744:Cell Line, Tumor; D006801:Humans; D020128:Inhibitory Concentration 50; D008958:Models, Molecular; D009705:Nucleosides / Q000138:chemical synthesis* / Q000737:chemistry / Q000378:metabolism / Q000494:pharmacology*; D019009:Proto-Oncogene Proteins c-kit / Q000378:metabolism; D015203:Reproducibility of Results; D013449:Sulfonamides / Q000737:chemistry*; D053778:Thiazolidines / Q000737:chemistry*
D000970:Antineoplastic Agents; D052160:Benzothiazoles; D009705:Nucleosides; D013449:Sulfonamides; D053778:Thiazolidines; D019009:Proto-Oncogene Proteins c-kit; C005465:benzothiazole