Synthesis of Two Estradiol-Imidazole C-Ribonucleoside Hybrid Compounds Exhibiting Inhibitory Effects against Type 1 17β-Hydroxysteroid Dehydrogenase

Heterocycles ◽  
2010 ◽  
Vol 81 (12) ◽  
pp. 2817 ◽  
Author(s):  
Shinya Harusawa ◽  
Chihiro Kojima ◽  
Kensuke Fujii ◽  
Yuusaku Yamashita ◽  
Tomoya Tanaka ◽  
...  
Keyword(s):  
Hydroxysteroid Dehydrogenase ◽  
Inhibitory Effects ◽  
Hybrid Compounds

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

2017 ◽  
Vol 13 ◽  
pp. 1303-1309 ◽  
Author(s):  
Ildikó Bacsa ◽  
Rebeka Jójárt ◽  
János Wölfling ◽  
Gyula Schneider ◽  
Bianka Edina Herman ◽  
...  
Keyword(s):  
Methyl Ether ◽  
Hydroxysteroid Dehydrogenase ◽  
Coupling Reactions ◽  
Sonogashira Coupling ◽  
Partial Saturation ◽  
Inhibitory Effects ◽  
Microwave Reactor ◽  
Incubation Method

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 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 17β-hydroxysteroid dehydrogenase type 1 isozyme (17β-HSD1) were investigated by an in vitro radiosubstrate incubation method. Certain 3-hydroxy-2-phenethynyl or -phenethyl derivatives proved to be potent 17β-HSD1 inhibitors, displaying submicromolar IC50 values.

Estradiol−Adenosine Hybrid Compounds Designed to Inhibit Type 1 17β-Hydroxysteroid Dehydrogenase

2005 ◽  
Vol 48 (26) ◽  
pp. 8134-8147 ◽  
Author(s):  
Donald Poirier ◽  
Roch P. Boivin ◽  
Martin R. Tremblay ◽  
Marie Bérubé, ◽  
Wei Qiu ◽  
...  
Keyword(s):  
Hydroxysteroid Dehydrogenase ◽  
Hybrid Compounds

The role of hepatic 11[b]-hydroxysteroid dehydrogenase type 1 in cholesterol homeostasis

2013 ◽  
pp. 1-1
Author(s):  
Kajal Manwani ◽  
Tak Y Man ◽  
Christopher J Kenyon ◽  
Ruth Andrew ◽  
Karen E Chapman ◽  
...  
Keyword(s):  
Hydroxysteroid Dehydrogenase ◽  
Cholesterol Homeostasis

Macrophage-specific 11b-hydroxysteroid dehydrogenase type 1 deficiency promotes angiogenesis but impairs resolution of K/BxN serum induced arthritis

2013 ◽  
pp. 1-1
Author(s):  
Zhenguang Zhang ◽  
Agnes Coutinho ◽  
Patrick Hadoke ◽  
Donald Salter ◽  
Jonathan Seckl ◽  
...  
Keyword(s):  
Hydroxysteroid Dehydrogenase

Suppression of 11[beta]-hydroxysteroid dehydrogenase type 1 target gene regulation by hypoxia

2016 ◽  
Author(s):  
Bushra Shammout ◽  
Adewonuola Alase ◽  
Miriam Wittmann ◽  
Paul Stewart ◽  
Ana Tiganescu
Keyword(s):  
Gene Regulation ◽  
Target Gene ◽  
Hydroxysteroid Dehydrogenase
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