Steroids p. 67 - 77 (2018)
Update date:2022-08-11
Topics:
Kiss, Anita
Mernyák, Erzsébet
W?lfling, János
Sinka, Izabella
Zupkó, István
Schneider, Gyula
The reduction of 16-hydroxymethylene-3-methoxy-13α-estra-1,3,5(10)-trien-17-one (14) and 16-hydroxymethylene-3-benzyloxy-13α-estra-1,3,5(10)-trien-17-one (16) yielded a mixture of two diastereomeric diols, the 16α-hydroxymethyl,17β-hydroxy and 16β-hydroxymethyl,17α-hydroxy isomers (17a-20a) in a ratio of 6:1. We describe a straightforward synthetic route to transform the isomers with trans functional groups attached to ring D (17a-20a) into isomers with cis functional groups (25a-28a). We determined the in vitro antiproliferative activities of compounds 17a–20a and 25a–28a by means of MTT assays against a panel of human adherent cancer cell lines HeLa, A2780, MCF-7, T47D, MDA-MB-231 and MDA-MB-361.
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Doi:10.1007/s00706-010-0352-y
(2010)Doi:10.1039/b109234k
(2002)Doi:10.1002/jps.2600631010
(1974)Doi:10.1246/bcsj.20180165
(2018)Doi:10.1021/acs.orglett.7b01287
(2017)Doi:10.1002/ejoc.200400314
(2004)