Fe(iii)-Catalyzed synthesis of steroidal imidazoheterocycles as potent antiproliferative agents

Fe(iii)-Catalyzed synthesis of steroidal imidazoheterocycles as potent antiproliferative agents Научная публикация

Журнал

Organic & Biomolecular Chemistry
ISSN: 1477-0520 , E-ISSN: 1477-0539

Вых. Данные

Год: 2020, Том: 18, Номер: 29, Страницы: 5571-5576 Страниц : 6 DOI: 10.1039/d0ob01241f

Авторы

Samanta Sadhanendu ¹ , Ghosh Asim Kumar ¹ , Ghosh Sumit ¹ , Ilina Anastasia A ² , Volkova Yulia A ² , Zavarzin Igor V ² , Scherbakov Alexander M ³ , Salnikova Diana I ^3,4 , Dzichenka Yaraslau U ⁵ , Sachenko Anton B ⁵ , Shirinian Valerii Z ² , Hajra Alakananda ¹

Организации

1	Department of Chemistry, Visva-Bharati (A Central University), Santiniketan, West Bengal, India
2	N.D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, 47 Leninsky prosp., 119991 Moscow, Russia
3	Department of Experimental Tumor Biology, N.N. Blokhin National Medical Research Center of Oncology, 24 Kashirskoe shosse, 115522 Moscow, Russia
4	Lomonosov Moscow State University, Faculty of Medicine, 27 Lomonosova prosp., Moscow 119192, Russia
5	Institute of Bioorganic Chemistry of NAS of Belarus, Laboratory of Protein Engineering, Academician V.F. Kuprevich str. 5/2, Minsk, Republic of Belarus

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.

Samanta S. , Ghosh A.K. , Ghosh S. , Ilina A.A. , Volkova Y.A. , Zavarzin I.V. , Scherbakov A.M. , Salnikova D.I. , Dzichenka Y.U. , Sachenko A.B. , Shirinian V.Z. , Hajra A.
Fe(iii)-Catalyzed synthesis of steroidal imidazoheterocycles as potent antiproliferative agents
Organic & Biomolecular Chemistry. 2020. V.18. N29. P.5571-5576. DOI: 10.1039/d0ob01241f WOS Scopus OpenAlex

Web of science:	WOS:000553219600005
Scopus:	2-s2.0-85088880889
OpenAlex:	W3041318943

БД	Цитирований
OpenAlex	35
Scopus	29
Web of science	28