4030-88-0

Upstream product

• 58-22-0 testosterone 
• 67-56-1 methanol 
• 62020-09-1 Methyl α-(methylsulfonyl)acetate 
• 2627-94-3 17β-acetoxy-6β-fluoro-4-androsten-3-one 
• 855-55-0 17β-acetoxy-6α-fluoro-4-androsten-3-one 
• 53-43-0 dehydroepiandrosterone 
• 521-17-5 5-androstenediol 
• 1045-69-8 testosterone acetate 
• 633-35-2 1,4,6-androstatriene-3,17-dione 
• 2352-19-4 androsta-4,6-dien-17β-ol-3-one acetate 
• 855-19-6 clostebol acetate 
• 633-34-1 androst-4,6-diene-3,17-dione 
• 115387-45-6 17β-benzoyloxy-androsta-4,6-dien-3-one 

Downstream Products

• 6947-46-2 17β-hydroxy-7α-propionylmercapto-androst-4-en-3-one 
• 7642-58-2 7α-methyl-17β-hydroxy-4-androsten-3-one 
• 50880-57-4 RMI 12936 
• 2352-19-4 androsta-4,6-dien-17β-ol-3-one acetate 
• 58-22-0 testosterone 
• 166819-03-0 17β-hydroxy-7β-phenpropylandrost-4-en-3-one 
• 166819-01-8 17β-hydroxy-7α-phenpropylandrost-4-en-3-one 
• 166819-07-4 7β-benzyl-17β-hydroxyandrost-4-en-3-one 
• 166819-02-9 17β-hydroxy-7β-phenethylandrost-4-en-3-one 
• 166819-00-7 17β-hydroxy-7α-phenethylandrost-4-en-3-one 

Relevant academic research and scientific papers

Chemoselective reduction of 1,4,6-cholestatrien-3-one and 1,4,6-androstatriene-3,17-dione by various hydride reagents

The chemoselectivity of rigid cyclic α,β-unsaturated carbonyl group on the reducing agents was influenced by the ring size and steric factor. Cholesterol (cholest-5-en-3β-ol) and dehydroepiandrosterone (DHEA) were oxidized with 2,3-dichloro-5,6-dicyano-1,4-benzoquinone to form 1,4,6-cholestatrien-3-one and 1,4,6-androstatriene-3,17-dione. They were reduced with NaBH4, lithium tri-sec-butylborohydride (l-Selectride), LiAlH4, 9-borabicyclo[3.3.1]nonane (9-BBN), lithium triethylborohydride (Super-hydride), and BH3·(CH3)2S in various conditions, respectively. Reduction of 1,4,6-cholestatrien-3-one and 1,4,6-androstatriene-3,17-dione by NaBH4 (4 equiv.) produced 4,6-cholestadien-3β-ol and 4,6-androstadiene-3β,17β-diol, respectively. Reduction by l-Selectride (12 equiv.) afforded 4,6-cholestadien-3α-ol and 4,6-androstadiene-3α,17β-diol, chemoselectively. Reaction with Super-hydride (12 equiv.) produced 4,6-cholestadien-3-one and 3-oxo-4,6-androstadien-17β-ol. Reduction of 1,4,6-cholestatrien-3-one by 9-BBN (14 equiv.) produced 1,4,6-cholestatrien-3α-ol, but 1,4,6-androstatriene-3,17-dione was not reacted with 9-BBN in the reaction conditions. Reaction of LiAlH4 (6 equiv.) formed 4,6-cholestadien-3β-ol and 3-oxo-1,4,6-androstatrien-17β-ol. Reduction of 1,4,6-cholestatrien-3-one by BH3·(CH3)2S (11 equiv.) gave cholestane as major compound and unlike reactivity of cholesterol, 1,4,6-androstatriene-3,17-dione by 8 equiv. of BH3·(CH3)2S formed 3-oxo-1,4,6-androstatrien-17β-ol. LiAlH4 and BH3·(CH3)2S showed relatively low chemoselectivity.

Testosterone I impurity preparation method

The invention discloses a testosterone I impurity preparation method, testosterone is used as a raw material, high-purity testosterone I impurity is prepared through dehydrogenation and purification,the purity of the obtained testosterone I impurity is greater than or equal to 99.5%, the prepared testosterone I impurity can be used as an impurity working reference substance, and accurate detection of testosterone related substances is realized. The method is simple and convenient to operate, easy to implement and high in preparation efficiency.

ANTI-CANCER NUCLEAR HORMONE RECEPTOR-TARGETING COMPOUNDS

The disclosure relates to anti-cancer compounds derived from nuclear steroid receptor binders, to products containing the same, as well as to methods of their use and preparation.

Iodine, a Mild Reagent for the Aromatization of Terpenoids

Efficient procedures based on the use of iodine for the aromatization of a series of terpenoids possessing diene and homoallylic or allylic alcohol functionalities are described. Different examples are reported as a proof-of-concept study. Furthermore, iodine also proved to mediate the dehydrogenation of testosterone.

The generation of a steroid library using filamentous fungi immobilized in calcium alginate Dedicated to the memory of Professor Sir John W. Cornforth, University of Sussex (1917-2013).

Four fungi, namely, Rhizopus oryzae ATCC 11145, Mucor plumbeus ATCC 4740, Cunninghamella echinulata var. elegans ATCC 8688a, and Whetzelinia sclerotiorum ATCC 18687, were subjected to entrapment in calcium alginate, and the beads derived were used in the biotransformation of the steroids 3β,17β-dihydroxyandrost-5-ene (1) and 17β-hydroxyandrost-4-en-3-one (2). Incubations performed utilized beads from two different encapsulated fungi to explore their potential for the production of metabolites other than those derived from the individual fungi. The investigation showed that steroids from both single and crossover transformations were typically produced, some of which were hitherto unreported. The results indicated that this general technique can be exploited for the production of small libraries of compounds.

Novel metabolites of dehydroepiandrosterone and progesterone obtained in Didymosphearia igniaria KCH 6670 culture

Dehydroepiandrosterone (DHEA) (10) and its five derivatives: testosterone (1), androstenedione (2), 17α-methyltestosterone (6), progesterone (13) and pregnenolone (14) were subjected to microbial transformation by the filamentous fungus Didymosphaeria igniaria KCH 6670. The predominant metabolism of the incubated 5-ene steroids (10 and 14) occurred through 3β-hydroxy-steroid dehydrogenase/5,4-en isomerase pathways resulting in the generation of a 4-en-3-oxo system on ring-A. The transformations of C 19 steroids (1, 2, and 10) included a hydroxylation at 7α position, ketone-alcohol interconversion at C-17 and reduction of the double bond at C-4 and 3-keto group to the 3β-alcohol with 5α- stereochemistry at A/B ring. D. igniaria also carried out 6(7)-dehydrogenation and 6,7β-epoxidation during transformation of DHEA. Under these conditions transformation of DHEA (10) gave four products: 7α-hydroxyandrost-4-en-3, 17-dione (4), 17β-hydroxyandrost-4,6-dien-3-one (11), 17β- hydroxyandrost-6β-epoxy-4-en-3-one (12) and 3β,17β-dihydroxy- 5α-androstane (5). The compounds 11 and 12 are identified as DHEA metabolites for the first time. The transformation of C21 steroids (13 and 14) led to the mixture of mono- (mainly 11α- and 15β-) and dihydroxy- (7α,15β-; 14α,15β-; 11α,15β-; 11α,14α-) products. 7α,15β-Dihydroxypregnan-4-en-3,20- dione (18) and 14α,15β-dihydroxypregnan-4-en-3,20-dione (19) were found to be new compounds. The main product of transformation of 17α-methyltestosterone (6) was 12β-hydroxy-17α- methyltestosterone (7). The results of these transformations demonstrate the dependence of hydroxylation position on the structure of steroid nucleus.

Stereoselective synthesis of some methyl-substituted steroid hormones and their in vitro cytotoxic activity against human gastric cancer cell line MGC-803

A series of 3-, 7-, 15-, and 16-methyl-substituted steroid analogs were synthesized via a highly stereoselective 1,6-conjugate addition. Under the catalysis of CuBr, AlMe3 reacted with four steroid dienone precursors to afford either the corresponding α-epimer of C-3 and C-7 methyl-substituted steroids as the major products, and the ratio of α/β was up to 10/1. No β-epimer has been detected for methyl addition at C-16. However, under the same reaction conditions, enantioselective methyl addition at C-15 afforded the 15β-epimer as the major product. The preliminary SAR analysis showed that the methyl substituents at C-7α and C-15β positions lead to a dramatical increase in potency against human gastric cancer cell line MGC-803.

Ergosteroids VII: perchloric acid-induced transformations of 7-oxygenated steroids and their bio-analytical applications--a liquid chromatographic-mass spectrometric study.

Sulfate esters of 7-oxo-delta(5)-steroids can be selectively and quantitatively hydrolyzed to the corresponding free steroids in the presence of carboxylic acid esters by solvolysis with perchloric acid in ethyl acetate at room temperature. Sulfates as well as carboxylic acid esters, methyl ethers, and ketals can be quantitatively converted to the corresponding 3,5-diene-7-one derivatives by heating with perchloric acid in methanol at 65 degrees C. The dienes have a strong UV absorption with maximum centered around 284 nm. These reactions have been used for the characterization and structural elucidation of 7-oxygenated-delta(5)-steroids that are present in complex biomatrices and can also be used for the quantitative estimation of total 7-oxo-delta(5)-steroids (free as well as conjugated) in biological matrices.

Novel cytokine release inhibitors. Part II: Steroids

Steroidal derivatives as IL-1β release inhibitors are discussed.