544693-34-7Relevant academic research and scientific papers
Pd-catalyzed Suzuki–Miyaura couplings and evaluation of 13α-estrone derivatives as potential anticancer agents
Ali, Hazhmat,Horváth, Gergely,Jójárt, Rebeka,Kele, Zoltán,Mernyák, Erzsébet,Zupkó, István
, (2020)
13α-Estrones are of great value owing to their potent multiple bioactivity, including anticancer activity. 3-OH or 3-OBn derivatives of 2- or 4-[(subst.) phenyl]-13α-estrone as potential antiproliferative agents have been synthesized via facile, microwave
Stereoselective synthesis of the four 16-hydroxymethyl-3-methoxy- and 16-hydroxymethyl-3-benzyloxy-13α-estra-1,3,5(10)-trien-17-ol isomers and their antiproliferative activities
Kiss, Anita,Mernyák, Erzsébet,W?lfling, János,Sinka, Izabella,Zupkó, István,Schneider, Gyula
, p. 67 - 77 (2018/03/21)
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.
Stereoselective synthesis of spiro and condensed pyrazolines of steroidal α,β-unsaturated ketones and nitrilimines by 1,3-dipolar cycloaddition
Mernyak, Erzsebet,Kozma, Eszter,Hetenyi, Anasztazia,Mark, Laszlo,Schneider, Gyula,Woelfling, Janos
body text, p. 520 - 525 (2009/05/07)
Effective syntheses of endo- and exocyclic α,β-unsaturated ketones as C{double bond, long}C dipolarophiles were carried out in the 13α-estrone series. The 1,3-dipolar cycloadditions of 15,16α,β-unsaturated ketones of 13α-estrone 3-methyl and 3-benzyl ethe
Synthesis and receptor-binding examinations of the normal and 13-epi-D-homoestrones and their 3-methyl ethers
Woelfling, Janos,Mernyak, Erzsebet,Frank, Eva,Falkay, George,Marki, Arpad,Minorics, Renata,Schneider, Gyula
, p. 277 - 288 (2007/10/03)
An effective epimerization of the normal estrone 3-methyl and 3-benzyl ethers by using o-phenylenediamine and AcOH made the possibility for facile entry into the 13α-estrone series. Combination of this synthetic methodology with an isolation step carried out by means of the Girard-P reagent, the corresponding ethers of 13-epi-estrone were obtained in excellent yields. The 3-hydroxy and 3-methoxy D-homoestrone derivatives in both the normal and the 13α-estrone series were then synthesized and tested in vitro in a radioligand-binding assay. The estrogen receptor recognizes these compounds, but their relative binding affinities (RBAs) are lower than that of the reference compound 3,17β-estradiol. The progesterone receptor-binding affinities of the four D-homo derivatives were also tested showing low values for 13α-D-homoestrone and its 3-methyl ether. Pharmacologically, these 13α-D-homoestrone derivatives are estrogen receptor-selective molecules.
