Role of Enaminonitriles in Heterocyclic Synthesis: Synthesis of Some New Aminothiazole Derivatives against Prostate Carcinoma

Abstract

Among sulfur- and nitrogen-containing heterocyclic compounds, the aminothiazole scaffold is one of the most unique architectures in drug development, since it comprises a variety of biological effects. Furthermore, numerous aminothiazole-based compounds have been widely used as medical drugs to treat a range of illnesses, resulting in a slew of new inventions. The synthetic procedures employed to get new aminothiazole derivatives from enaminonitrile acrylamide derivative 2, which was previously used as a key step in the synthesis of pyrazole, isoxazole, and pyrimidine derivatives, are innovative (4, 6 and 8). In addition, enaminonitrile 2 showed chemical activity toward some N-nucleophiles such as heterocyclic amines for synthesis triazolo, imidazo and pyrazolo pyrimidine derivatives (10, 12, and 14). Enaminonitrile precursor 2 was cyclocondensed with various carbon and oxygen nucleophiles to provide some complex polyfunctionally substituted fused 2-pyridone and chromenone derivatives with a thiazoyl sulfonamido moiety (16, 18, 20, and 24). The anticancer efficacy of all novel aminothiazoles was tested in vitro against human prostate carcinoma (PC3) utilizing normal prostate epithelial cell line (PNT2) as control cells. The most powerful derivatives against prostate cancer cell lines were determined to be 14 and 16, which had no impact on normal cells. Compound 20 on the other hand, has just mediocre anticancer properties.