Fe(iii)-Catalyzed synthesis of steroidal imidazoheterocycles as potent antiproliferative agents. Issue 29 (14th July 2020)

• Record Type: Journal Article
• Authors: Samanta, Sadhanendu; Ghosh, Asim Kumar; Ghosh, Sumit; Ilina, Anastasia A.; Volkova, Yulia A.; Zavarzin, Igor V.; Scherbakov, Alexander M.; Salnikova, Diana I.; Dzichenka, Yaraslau U.; Sachenko, Anton B.; Shirinian, Valerii Z.; Hajra, Alakananda
• Is Part Of: Organic & biomolecular chemistry. Volume 18:Issue 29(2020)
• Page Start: 5571
• Page End: 5576
• Publication Date: 2020-07-14
• Subjects: Chemistry, Organic -- Periodicals; Bioorganic chemistry -- Periodicals; Chemistry, Physical organic -- Periodicals; 547
• DOI: 10.1039/d0ob01241f
• Languages: English
• ISSNs: 1477-0520

Abstract

Abstract : An efficient and practical method has been developed for the synthesis of steroidal imidazo[1, 2- a ]pyridines as potent antiproliferative agents via FeCl3 -catalyzed oxidative amination in high yields. Abstract : An efficient and practical method has been developed for the synthesis of steroidal imidazoheterocycles via cost-effective and environmentally benign FeCl3 -catalyzed oxidative amination. A library of steroidal imidazo[1, 2- a ]pyridines was directly synthesized from readily available 2-aminopyridines and steroidal ketones in aerobic conditions. The synthesized compounds were screened for activity on human microsomal cytochrome P450s CYP7, CYP17 and CYP21. Antiproliferative activity of two lead compounds 3ia and 3la was additionally evaluated against the human MCF-7 (breast cancer), SKOV3 (ovarian cancer), and 22Rv1 (prostate cancer) cell lines. Steroidal imidazo[1, 2- a ]pyridine 3la which is a substrate molecule for CYP17A1 with IC50 = 1.7 μM (MCF-7), 3.0 (SKOV3), and 6.0 μM (22Rv1) has proved to be more active than reference drug cisplatin.