1229-12-5Relevant articles and documents
X-ray and deuterium labeling studies on the abnormal ring cleavages of a 5β-epoxide precursor of formestane
Tavares Da Silva, Elisiario J,Roleira, Fernanda M.F,Sa E Melo, M.Luisa,Campos Neves, Andre S,Paixao, Jose A,De Almeida, Maria J,Silva, Manuela R,Andrade, Lourdes C.R
, p. 311 - 319 (2002)
A new convergent synthesis of the antitumor steroid formestane (4-OHA) 5 has been performed from the easily available epimeric mixture of 5α- and 5β-androst-3-en-17-one 1a and 1b in order to attempt a yield improvement. A two-step oxidative route followed by base-catalyzed isomerization was applied to the 5α- and 5β-epimers 1a and 1b, either as a mixture or separately, leading to the title compound 5. From epimer 1a an efficient process was attained to prepare the desired aromatase inhibitor formestane. Epimer 1b led to the formation of the same compound 5. Additionally, 1b have also been converted in 5β-hydroxyandrostane-3,17-dione 12 and androst-4-ene-3,17-dione 13, revealing an unexpected reactivity of the 3β,4β-epoxy-5β-androstan-17-one intermediate 6 formed from 1b during the first oxidative step with performic acid. Cleavage of the epoxide 6 led to the trans-diaxial and the trans-diequatorial vic-diols 7 and 8 and to the 1,3-diol 9. The formation of the abnormal products 8 and 9 were investigated through X-ray and deuterium labeling studies. Diol 8 was formed through a trans-diequatorial epoxide ring opening and the 1,3-diol 9 was formed through an intramolecular rearrangement involving a 1,2-hydride shift. All the vic-diols 3, 7 and 8 formed, proved to be good precursors for the synthesis of the target compound 5. Copyright
Platinum supported on TiO2 as a new selective catalyst on heterogeneous hydrogenation of α,β-unsaturated oxosteroids
Nunes, Rui M.D.,MacHado, Bruno F.,Pereira, Mariette M.,Moreno, Maria José S.M.,Faria, Joaquim L.
, p. 1 - 5 (2010)
This paper describes the photochemical deposition of platinum onto TiO 2 surface and the full characterization of the catalysts using BET, XPS and TEM techniques. The 1 and 3 wt. % Pt/TiO2 catalysts reveal high activity with 70% and 96% of α-diastereoselectivity in the hydrogenation of the carbon-carbon double bond of the α,β-unsaturated oxosteroids 4-androstene-3,17-dione, and 3β-acetoxypregna-5,16-dien-20- one, respectively. Using higher temperature and pressure, the catalysts promote the further reduction of C-3 carbonyl group. Catalyst recovering and recycling is easily achieved with no appreciable lost of catalytic activity after five subsequent runs.
Synthesis and biological evaluation of steroidal derivatives bearing a small ring as vitamin D receptor agonists
Arichi, Norihito,Fujiwara, Shinichi,Ishizawa, Michiyasu,Makishima, Makoto,Hua, Duy H.,Yamada, Ken-ichi,Yamaoka, Yousuke,Takasu, Kiyosei
, p. 3408 - 3411 (2017)
A novel series of 3-ketolithocholic acid derivatives as well as estrone derivatives bearing a small ring for the conformational fixation of the side chain were synthesized by using a catalytic [2+2] cycloaddition and a ring-contraction rearrangement. The steroidal derivatives were evaluated for transcriptional activation of vitamin D receptor by luciferase reporter assays. Among them, two estrone derivatives showed a higher efficacy of the transactivation of vitamin D receptor than 3-ketolithocholic acid, and the small ring moieties were found to be important for the efficacy.
5β-Androstan-3,17-dione
Anthony, Addlagatta,Jaskolski, Mariusz,Nangia, Ashwini,Desiraju, Gautam R.
, p. 1898 - 1900 (1998)
The title compound, C19H28O2, has the 5β configuration and a bowing angle of 71.76(5)° at the A/B ring junction. The crystal structure is stabilized by weak intermolecular C-H...O and van der Waals interactions.
Synthesis of Cardiotonic Steroids Oleandrigenin and Rhodexin B
Fejedelem, Zachary,Carney, Nolan,Nagorny, Pavel
, p. 10249 - 10262 (2021/07/31)
This article describes a concise synthesis of cardiotonic steroids oleandrigenin (7) and its subsequent elaboration into the natural product rhodexin B (2) from the readily available intermediate (8) that could be derived from the commercially available steroids testosterone or DHEA via three-step sequences. These studies feature an expedient installation of the β16-oxidation based on β14-hydroxyl-directed epoxidation and subsequent epoxide rearrangement. The following singlet oxygen oxidation of the C17 furan moiety provides access to oleandrigenin (7) in 12 steps (LLS) and a 3.1% overall yield from 8. The synthetic oleandrigenin (7) was successfully glycosylated with l-rhamnopyranoside-based donor 28 using a Pd(II)-catalyst, and the subsequent deprotection under acidic conditions provided cytotoxic natural product rhodexin B (2) in a 66% yield (two steps).
Steroid compound, application and preparation method thereof
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Paragraph 0225-0226; 0239, (2020/07/24)
The invention relates to a steroid compound, an application and a preparation method thereof. The compounds are expected to be capable of effectively treating neuropsychiatric diseases, and have goodactive efficacy, pharmacokinetic (PK) performance, oral
Method for synthesizing stanozolol intermediate androstane-17alpha-methyl-17beta-hydroxyl-3-ketone
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, (2019/04/09)
The invention provides a method for synthesizing a stanozolol intermediate androstane-17alpha-methyl-17beta-hydroxyl-3-ketone. The method comprises the following steps: taking 4-androstenedione as a raw material, carrying out 3-site and 17-site keto-double-ketal, 5-site ethylenic bond catalytic hydrogenation and 3-site and 17-site double-ketal hydrolysis to prepare a compound 5alpha-androstane-3,17-diketone; then carrying out 3-site keto-double-etherification and 17-site Grignard addition, and finally carrying out hydrolysis to prepare the compound androstane-17alpha-methyl-17beta-hydroxyl-3-ketone, wherein the HPLC (High Performance Liquid Chromatography) purity of the compound is 99.0% or greater. The method provided by the invention is short in route, easy in production process control,environmentally-friendly, low in production cost and applicable to industrial large-scale production.
