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Synthesis of novel 13?-estrone derivatives by Sonogashira coupling as potential 17?-HSD1 inhibitors.

ABSTRACT: Novel 13?-estrone derivatives were synthesized by Sonogashira coupling. Transformations of 2- or 4-iodo regioisomers of 13?-estrone and its 3-methyl ether were carried out under different conditions in a microwave reactor. The 2-iodo isomers were reacted with para-substituted phenylacetylenes using Pd(PPh3)4 as catalyst and CuI as a cocatalyst. Coupling reactions of 4-iodo derivatives could be achieved by changing the catalyst to Pd(PPh3)2Cl2. The product phenethynyl derivatives were partially or fully saturated. Compounds bearing a phenolic OH group furnished benzofurans under the conditions used for the partial saturation. The inhibitory effects of the compounds on human placental 17?-hydroxysteroid dehydrogenase type 1 isozyme (17?-HSD1) were investigated by an in vitro radiosubstrate incubation method. Certain 3-hydroxy-2-phenethynyl or -phenethyl derivatives proved to be potent 17?-HSD1 inhibitors, displaying submicromolar IC50 values.

SUBMITTER: Bacsa I 

PROVIDER: S-EPMC5496578 | biostudies-literature | 2017

REPOSITORIES: biostudies-literature

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

Bacsa Ildikó I   Jójárt Rebeka R   Wölfling János J   Schneider Gyula G   Herman Bianka Edina BE   Szécsi Mihály M   Mernyák Erzsébet E  

Beilstein journal of organic chemistry 20170630

Novel 13α-estrone derivatives were synthesized by Sonogashira coupling. Transformations of 2- or 4-iodo regioisomers of 13α-estrone and its 3-methyl ether were carried out under different conditions in a microwave reactor. The 2-iodo isomers were reacted with <i>para</i>-substituted phenylacetylenes using Pd(PPh<sub>3</sub>)<sub>4</sub> as catalyst and CuI as a cocatalyst. Coupling reactions of 4-iodo derivatives could be achieved by changing the catalyst to Pd(PPh<sub>3</sub>)<sub>2</sub>Cl<sub  ...[more]

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