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Steroidal N-Sulfonylimidates: Synthesis and biological evaluation in breast cancer cells.

Abstract：

:Unique derivatives of androstene and estrane series containing N-sulfonylimidate pendants were prepared from 17α-ethynyl steroids via Cu-catalyzed azide-alkyne cycloaddition to tosyl azide in the presence of alcohols. The synthesized compounds were screened for cytotoxicity against human breast cancer cell lines and ERα agonist activity. The hit compound 3,17β-dimethoxy-17α-[iso-propyl-2'-N-tosylacetimidate]estra-1,3,5(10)-triene (4n) had no ERα-mediated hormonal activity and was found to exhibit potent cytotoxic effect in an ERα-positive breast cancer cell line. N-Sulfonylimidate 4n displayed high antiproliferative potency against triple-negative MDA-MB-231 breast cancer cells, while it was non-toxic towards normal mammary epithelial cells. Compound 4n was found to alter activity of various signaling pathways (NF-κB, Slug, cyclin D1, ERK) supporting the growth and invasiveness of tumor cells.

journal_name

Eur J Med Chem

journal_title

European journal of medicinal chemistry

authors

Volkova YA,Kozlov AS,Kolokolova MK,Uvarov DY,Gorbatov SA,Andreeva OE,Scherbakov AM,Zavarzin IV

doi

10.1016/j.ejmech.2019.06.048

subject

Has Abstract

pub_date

2019-10-01 00:00:00

pages

694-706

eissn

0223-5234

issn

1768-3254

pii

S0223-5234(19)30575-6

journal_volume

179

pub_type

杂志文章

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