Pd-Catalyzed microwave-assisted synthesis of phosphonated 13α-estrones as potential OATP2B1, 17β-HSD1 and/or STS inhibitors

• Rebeka Jójárt,
• Szabolcs Pécsy,
• György Keglevich,
• Mihály Szécsi,
• Réka Rigó,
• Csilla Özvegy-Laczka,
• Gábor Kecskeméti and
• Erzsébet Mernyák

Beilstein J. Org. Chem. 2018, 14, 2838–2845, doi:10.3762/bjoc.14.262

• ; enzyme; 13α-estrone; Hirao reaction; 17β-HSD1 inhibition; OATP2B1; STS; Introduction The biosynthesis of estrogens occurs via various enzymatic routes. Cytochrome P450 aromatase catalyzes the conversion of nonaromatic steroids to estrogens [1]. Moreover, hydrolysis of estrone 3-sulfate, existing as a

• reactiona of 2- or 4-bromo-13α-estrones 1–6 with diethyl phosphite (7a) or diphenylphosphine oxide (7b). OATP2B1, STS and 17β-HSD1 inhibition data of C–P coupled products 8–13 and their basic compounds 13αE1OMe, 13αE1OH, 13αE1OBn. Supporting Information Supporting Information File 378: General synthetic

Synthesis of novel 13α-estrone derivatives by Sonogashira coupling as potential 17β-HSD1 inhibitors

• Ildikó Bacsa,
• Rebeka Jójárt,
• János Wölfling,
• Gyula Schneider,
• Bianka Edina Herman,
• Mihály Szécsi and
• Erzsébet Mernyák

Beilstein J. Org. Chem. 2017, 13, 1303–1309, doi:10.3762/bjoc.13.126

• 17β-HSD1 inhibitors, displaying submicromolar IC50 values. Keywords: benzofuran; 13α-estrone; 17β-HSD1 inhibition; partial saturation; Sonogashira coupling; Introduction Synthetic modifications of the naturally occurring female prehormone estrone may lead to compounds with diverse biological

• compounds may provide promising candidates for drug development in order to get nanomolar inhibitors. Syntheses of 2- or 4-phenethynyl-13α-estrones (8–11) by Sonogashira coupling. Partial or full hydrogenation of compounds 8c–11c. 17β-HSD1 inhibition data of Sonogashira coupled compounds and their