Synthesis and antiproliferative activity evaluation of steroidal imidazo[1,2-a]pyridines

Synthesis and antiproliferative activity evaluation of steroidal imidazo[1,2-a]pyridines Full article

Journal

Steroids
ISSN: 1878-5867 , E-ISSN: 0039-128X

Output data

Year: 2016, Volume: 113, Pages: 29-37 Pages count : 9 DOI: 10.1016/j.steroids.2016.06.001

Authors

Rassokhina Irina V. ¹ , Volkova Yulia A. ¹ , Kozlov Andrey S. ¹ , Scherbakov Alexander M. ² , Andreeva Olga E. ² , Shirinian Valerik Z. ¹ , Zavarzin Igor V. ¹

Affiliations

1	N. D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, Leninsky prosp. 47, 119991 Moscow, Russia
2	N. N. Blokhin Russian Cancer Research Center, Kashirskoye shosse 24, 115478 Moscow, Russia

An elegant approach to unknown steroidal imidazo[1,2-a]pyridine hybrids is disclosed. Unique derivatives of androstene and estrane series containing imidazo[1,2-a]pyridine motifs were prepared from 17-ethynyl steroids in good yields via copper-catalyzed cascade aminomethylation/cycloisomerization with imines. The synthesized compounds were screened for cytotoxicity against human breast (MCF-7, MDA-MB-231, HBL-100, MDA-MB-453) and prostate (LNCaP-LN3, PC-3, DU 145) cancer cell lines. The majority of tested compounds showed activities at μM level in breast cancer cells. The hormone-responsive breast cancer cells MCF-7 were more sensitive to novel compounds than ERα-negative cells; in particular, compounds 6a,b exhibited promising cytotoxicity against this cell line with the IC50 values in the range of 3–4 μM. Furthermore, compound 4a showed remarkable effects as a selective ERα receptor modulator.

Rassokhina I.V. , Volkova Y.A. , Kozlov A.S. , Scherbakov A.M. , Andreeva O.E. , Shirinian V.Z. , Zavarzin I.V.
Synthesis and antiproliferative activity evaluation of steroidal imidazo[1,2-a]pyridines
Steroids. 2016. V.113. P.29-37. DOI: 10.1016/j.steroids.2016.06.001 WOS Scopus OpenAlex

Web of science:	WOS:000382341400005
Scopus:	2-s2.0-84975263373
OpenAlex:	W2409988171

DB	Citing
OpenAlex	45
Scopus	41
Web of science	37