481-29-8Relevant academic research and scientific papers
Synthesis and antituberculosis activity of several steroids from 3αacetoxy-5βpregn-16-En-20-one
Sikharulidze,Nadaraia,Kakhabrishvili
, p. 423 - 425 (2012)
The semicarbazone and isonicotinoylhydrazone of 5βpregn-2-en-20-one, which was prepared from 3βacetoxy-5βpregn-16-en-20-one, were synthesized for the first time. The antituberculosis activity of these and semicarbazones and isonicotinoylhydrazones of saturated, unsaturated, and adamantane-modified ketosteroids synthesized by us earlier was studied in vitro experiments.
UNUSUAL HIGH REACTIVITIES OF Δ5 STEROIDS IN PALLADIUM CATALYZED HYDROGENATION
Nishimura, Shigeo,Takahashi, Izumi,Shiota, Michio,Ishige, Masayoshi
, p. 877 - 878 (1981)
Hydrogenation of a mixture of 3β-hydroxyandrost-5-en-17-one or cholesterol with α-pinene has revealed that the Δ5 steroids are more reactive than α-pinene over palladium while α-pinene is much more reactive than the Δ5 steroids with other platinum metals.
ANDROSTENEDIONE METABOLISM IN EPITHELIAL CELLS DERIVED FROM EARLY-LACTATION HUMAN MILK
Perel, E.,Stolee, K. J.,Kharlip, L.,Blackstein, M. E.,Killinger, D. W.
, p. 389 - 400 (1983)
Epithelial cells derived from duct epithelium were cultured from early lactation human milk in medium supplemented with 15percent fetal calf serum, insulin (0.3 u/ml), cortisol 21-sodium succinate (6 μg/ml) and amikacin (50 μg/ml).The capacity of these cells to metabolize androstenedione to estrone, estradiol and C19 metabolites was studied during continuous culture.After extraction of the medium, the products were subjected to phenolic partition and separated by thin-layer and paper chromatography, followed by recrystallization to constant specific activity.The study demonstrated a progressive increase in the formation of estrone and testosterone over the first 24 h in culture, while estradiol formation showed an initial 2-4 h lag, then increased slowly.The C19 compounds identified were androsterone, 5α-androstanedione, epiandrosterone, dihydrotestosterone and etiocholanolone. 5α-Androstanedione and androsterone were the major 5α-reduced metabolites.Since these cells are derived from normal duct epithelium, their metabolic characteristics may be more representative of normal breast tissue than those of tissue removed from patients with pathological breast disorders.
Synthesis of guggulsterone derivatives as potential anti-austerity agents against PANC-1 human pancreatic cancer cells
Kohyama, Aki,Yokoyama, Rei,Dibwe, Dya Fita,El-Mekkawy, Sahar,Meselhy, Meselhy R.,Awale, Suresh,Matsuya, Yuji
, (2020)
E- and Z-guggulsterones and nine guggulsterone derivatives (GSDs) were synthesized and evaluated for their preferential cytotoxicity against human PANC-1 cell in nutrient deprived medium utilizing antiausterity strategy. Among the synthesized compounds, GSD-1 and GSD-7 showed potent cytotoxicity against PANC-1 cells under nutrient-deprived conditions in a concentration dependent manner, with a PC50 value of 1.6 μM and 3.2 μM, respectively. The effect of GSD-1 and GSD-7 was further evaluated in a real time using live cell imaging. Both of these compounds altered PANC-1 cell morphology, leading to cell death at sub micromolar concentration range. GSD-1 and GSD-7 also inhibited PANC-1 cell colony formation in a concentration-dependent manner. GSD-1 and GSD-7 are lead structure for the anti-austerity drug development.
Photoinduced Deoxygenative Borylations of Aliphatic Alcohols
Wu, Jingjing,B?r, Robin M.,Guo, Lin,Noble, Adam,Aggarwal, Varinder K.
, p. 18830 - 18834 (2019/11/22)
A photochemical method for converting aliphatic alcohols into boronic esters is described. Preactivation of the alcohol as a 2-iodophenyl-thionocarbonate enables a novel Barton–McCombie-type radical deoxygenation that proceeds efficiently with visible light irradiation and without the requirement for a photocatalyst, a radical initiator, or tin or silicon hydrides. The resultant alkyl radical is intercepted by bis(catecholato)diboron, furnishing boronic esters from a diverse range of structurally complex alcohols.
Catalytic removal of tert-butyldimethylsilyl (TBS) ether by PVP-I
Ke, Yanxiong,Lu, Guangying,Ren, Jiangmeng,Wang, Di,Zeng, Bu-Bing
, (2019/09/06)
A mild, efficient and rapid protocol the deprotection of alcoholic TBDMS ethers using PVP-1 as catalyst in methanol, the procedure of deprotection of various TBDMS ethers were found to be very convenient, easy work-up, high yielding.
Steroid compound 3-site hydroxyl configuration inversion method
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Paragraph 0037; 0042; 0043, (2018/12/14)
The invention discloses a steroid compound 3-site hydroxyl configuration inversion method. The method specifically comprises the following steps that (1) a steroid compound containing a 3-site hydroxyl reacts with an acyl chloride compound; (2) the product obtained in the step (1) and a substituting agent are subjected to SN2 nucleophilic substitution reaction under existing of a phase transfer catalyst; and (3) the product obtained in the step (2) is subjected to a hydrolysis reaction. Compared with a Mitsunobu method, the method does not need to use triphenylphosphine and azodiformate pricedhigher, and accordingly the production cost is greatly lowered; meanwhile, a p-nitrobenzoic acid derivative which seriously affects the water environment does not need to be used, and therefore the method is more environmentally friendly. The method adopts cesium acetate/18-crown ether-6 system to conduct 3-site hydroxyl configuration inversion, can remarkably reduce occurrence of side reactions,accordingly a higher reaction yield is obtained, and the method is finally applicable to industrialized production.
Abiraterone acetate reducing impurity and preparation method thereof
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Paragraph 0017, (2017/10/22)
The invention discloses an abiraterone acetate reducing impurity and a preparation method thereof. The impurity is 17-(3-pyridyl) androstane-3 beta-acetoxyl. The preparation method of the impurity includes the steps: taking dehydroepiandrosterone as a starting material; performing catalytic hydrogenation by palladium carbon to obtain (3 beta)-3-hydroxy-17-sterone; performing reaction by hydrazine hydrate to obtain 17-hydrazono-androstane-3 beta-alcohol; performing iodine substitution to obtain 17-iodine-androstane-3 beta-alcohol; reacting the 17-iodine-androstane-3 beta-alcohol with borane reagents under palladium catalysis to obtain 17-(3-pyridyl) androstane-3 beta-alcohol; performing acetic anhydride acetylation to obtain the abiraterone acetate reducing impurity 17-(3-pyridyl) androstane-3 beta-acetoxyl.
New technology for synthesizing epiandrosterone by using 3beta-hydroxypregna-16-ene-20-one-3-acetate
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Paragraph 0017; 0041; 0042, (2017/08/30)
The invention provides a new technology for synthesizing epiandrosterone by using 3beta-hydroxypregna-16-ene-20-one-3-acetate. The new technology comprises the following steps of using the 3beta-hydroxypregna-16-ene-20-one-3-acetate as raw materials; oximating, rearranging, alcoholizing and hydrolyzing, so as to obtain the epiandrosterone. The new technology has the characteristics that the total yield rate of the epiandrosterone is 78% or above; by adopting the technical scheme, the hydrogenation reaction is not needed, the reaction condition is mild, and the problem of overhigh industrial cost caused by using palladium chloride-calcium carbonate as a catalyst in the traditional method is solved; the amount of byproducts is small; the operation is simple, the pollution is little, the yield rate is high, and the like; the new technology is suitable for industrialized production.
NEUROACTIVE STEROIDS, COMPOSITIONS, AND USES THEREOF
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Paragraph 0528; 0529; 0530, (2016/02/16)
Provided are methods of evaluating or treating a patient, e.g., a patient having a disorder described herein, comprising: a) optionally, acquiring a patient sample; b) acquiring an evaluation of and/or evaluating the sample for an alteration in the level S24(S)-hydroxycholesterol compared to a reference standard.
