6218-29-7Relevant academic research and scientific papers
Preparation method of estra-4,9-diene-3,17-dione
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, (2018/05/30)
The invention relates to the technical field of processing pharmaceutical intermediates, and particularly relates to a preparation method of estra-4,9-diene-3,17-dione. The method comprises the following steps: (1) carbonyl reduction reaction; (2) hydroxyl protection reaction; (3) substitution reaction; (4) double bond reduction reaction; (5) ketal hydrolysis reaction; (6) cyclization reaction; (7) substitution reaction; (8) ketal hydrolysis reaction; (9) cyclization reaction; (10) hydroxyl deprotection reaction; and (11) hydroxyl oxidation reaction. Reagents used in the method are light in environmental pollution and meet requirements of green chemistry; required raw materials are simple, and easily available and can facilitate industrial production; and the route is simple, the operationis easy, and the control is easy.
Regio- and stereoselective reduction of 17-oxosteroids to 17β-hydroxysteroids by a yeast strain Zygowilliopsis sp. WY7905
Liu, Yuanyuan,Wang, Yu,Chen, Xi,Wu, Qiaqing,Wang, Min,Zhu, Dunming,Ma, Yanhe
, p. 17 - 24 (2016/12/22)
The reduction of 17-oxosteroids to 17β-hydroxysteroids is one of the important transformations for the preparation of many steroidal drugs and intermediates. The strain Zygowilliopsis sp. WY7905 was found to catalyze the reduction of C-17 carbonyl group of androst-4-ene-3,17-dione (AD) to give testosterone (TS) as the sole product by the constitutive 17β-hydroxysteroid dehydrogenase (17β-HSD). The optimal conditions for the reduction were pH 8.0 and 30 °C with supplementing 10 g/l glucose and 1% Tween 80 (w/v). Under the optimized transformation conditions, 0.75 g/l AD was reduced to a single product TS with >90% yield and >99% diastereomeric excess (de) within 24 h. This strain also reduced other 17-oxosteroids such as estrone, 3β-hydroxyandrost-5-en-17-one and norandrostenedione, to give the corresponding 17β-hydroxysteroids, while the C-3 and C-20 carbonyl groups were intact. The absence of by-products in this microbial 17β-reduction would facilitate the product purification. As such, the strain might serve as a useful biocatalyst for this important transformation.
A simple method for the small scale synthesis and solid-phase extraction purification of steroid sulfates
Waller, Christopher C.,McLeod, Malcolm D.
supporting information, p. 74 - 80 (2015/02/19)
Steroid sulfates are a major class of steroid metabolite that are of growing importance in fields such as anti-doping analysis, the detection of residues in agricultural produce or medicine. Despite this, many steroid sulfate reference materials may have limited or no availability hampering the development of analytical methods. We report simple protocols for the rapid synthesis and purification of steroid sulfates that are suitable for adoption by analytical laboratories. Central to this approach is the use of solid-phase extraction (SPE) for purification, a technique routinely used for sample preparation in analytical laboratories around the world. The sulfate conjugates of sixteen steroid compounds encompassing a wide range of steroid substitution patterns and configurations are prepared, including the previously unreported sulfate conjugates of the designer steroids furazadrol (17β-hydroxyandrostan[2,3-d]isoxazole), isofurazadrol (17β-hydroxyandrostan[3,2-c]isoxazole) and trenazone (17β-hydroxyestra-4,9-dien-3-one). Structural characterization data, together with NMR and mass spectra are reported for all steroid sulfates, often for the first time. The scope of this approach for small scale synthesis is highlighted by the sulfation of 1 μg of testosterone (17β-hydroxyandrost-4-en-3-one) as monitored by liquid chromatography-mass spectrometry (LCMS).
11β-alkyl-Δ9-19-nortestosterone derivatives: High-affinity ligands and potent partial agonists of the androgen receptor
Muddana, Smita S.,Price, Aimee M.,MacBride, Megan M.,Peterson, Blake R.
, p. 4985 - 4988 (2007/10/03)
We report the synthesis of novel steroidal androgen receptor ligands comprising 11β-alkyl-Δ9-derivatives of 19-nortestosterone. These compounds are structurally related to the antiprogestin, antiglucocorticoid, and antiandrogen drug mifepristone (RU486). Nortestosterone analogues bearing 11β-octyl and 11β-decyl side-chains bind tightly to recombinant AR protein (IC50 = 6.6 nM and IC50 = 0.8 nM), block AR dimerization, exhibit activity against LNCaP prostate cancer cells, and comprise partial AR agonists with low antiglucocorticoid activity.
Antiglucocorticoid steroids for the treatment of anxiety disorders
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, (2008/06/13)
The invention relates to the use of antiglucocorticoid steroids for the manufacture of a pharmaceutical composition for the treatment of anxiety disorders.
11,21-BISPHENYL-19-NORPREGNANE DERIVATIVES
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, (2008/06/13)
The invention relates to a 11,21-bisphenyl-19-norpregnane derivative of formula I STR1 wherein R 1 is selected from H, halogen, (1-6C) alkoxy, and NR 5 R 6, R 5 and R 6 being independently hydrogen or (1-6C)alkyl or R 5 and R 6 together are (3-6C) alkylen
Biosynthesis of Estrogens. Estr-5(10)-ene-3,17-dione: Isolation, Metabolism and Mechanistic Implications
Ranjith, H.,Dharmaratne, W.,Kilgore, James L.,Roitman, Esther,Shackleton, Cedric,Caspi, Eliahu
, p. 1529 - 1536 (2007/10/02)
The 16-2H2 title compound 5b constituted a significant amount of the non-aromatic metabolites recovered from incubations of 3,17-dioxo-2H3>androst-4-en-19-al 1 with placental aromatase.For the evaluation of the role of compound 5b in the elaboration of estrogens, its transformations at pH 6.5 and 7.2 in the presence and absence of microsomal placental aromatase were investigated.In the presence of the aromatase at pH 6.5, estrogens (6.8percent), products of isomerization of the double bond (Δ5(10) -> Δ4) and products of reduction of the carbonyl groups were formed.When the incubation was carried out at pH 7.2, products similar to those obtained above were isolated but in different yields.Noticeably more estrogens (22.7percent) and less of the reduced products were formed.Additionally, at pH 7.2, 10β-hydroxy-2H2>estr-4-ene-3,17-dione 4a was obtained.In the absence of the aromatase, which was replaced with bovine albumin at both pH 6.5 and 7.2, 2H2>estr-4-ene-3,17-dione 3a and its 10β-hydroxy derivative 4a were formed in large amounts and were the only products detected.The ramifications of our observations in the context of estrogen biosynthesis are discussed.
