516-53-0Relevant articles and documents
Substrate specificity and inhibitor sensitivity of rabbit 20α-hydroxysteroid dehydrogenase
Endo, Satoshi,Arai, Yuki,Hara, Akira,Kitade, Yukio,Bunai, Yasuo,El-Kabbani, Ossama,Matsunaga, Toshiyuki
, p. 1514 - 1518 (2013/10/08)
In this study, we examined the substrate specificity and inhibitor sensitivity of rabbit 20α-hydroxysteroid dehydrogenase (AKR1C5), which plays a role in the termination of pregnancy by progesterone inactivation. AKR1C5 moderately reduced the 3-keto group of only 5α-dihydrosteroids with 17β- or 20α/β-hydroxy group among 3-ketosteroids. In contrast, the enzyme reversibly and efficiently catalyzed the reduction of various 17- and 20-ketosteroids, including estrogen precursors (dehydroepiandrosterone, estrone and 5α-androstan-3β- ol-17-one) and tocolytic 5β-pregnane-3,20- dione. In addition to the progesterone inactivation, the formation of estrogens and metabolism of the tocolytic steroid by AKR1C5 may be related to its role in rabbit parturition. AKR1C5 also reduced various non-steroidal carbonyl compounds, including isatin, an antagonist of the C-type natriuretic peptide receptor, and 4-oxo-2-nonenal, suggesting its roles in controlling the bioactive isatin and detoxification of cytotoxic aldehydes. AKR1C5 was potently and competitively inhibited by flavonoids such as kaempferol and quercetin, suggesting that its activity is affected by ingested flavonoids.
PROGESTERONE RECEPTOR ANTAGONISTS AND USES THEREOF
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Page/Page column 46, (2011/11/30)
The present invention relates to a compound of formula (I): for its use as progesterone receptor antagonist, in particular for its use for the prevention and/or the treatment of cancer or uterine pathologies.
Borane Reduction of the Steroid 20-Ketone Group in the Presence of Various Chiral β-Amino Alcohols
Goendoes, Gyoergy,Orr, James C.
, p. 581 - 582 (2007/10/02)
The direction of reduction of 20-carbonyl group of 3α-hydroxy-5β-pregnan-20-one (1) with a complex of borane-methyl sulfide and chiral β-amino alcohols, depends on the chirality of the amino alcohol.Where there is a 2-phenyl or 2-benzyl substituent, then the S enantiomer gives exclusively the steroid 20R alcohol 3.The R enantiomer of 2-amino-2-phenyl-1-ethanol gives the highest steroid 20S (2) : 20R (3) alcohol ratio. Key Words: 5β-Pregnane, 3α-hydroxy-20-one / Chiral borane reduction / Borane reduction / Steroids