510-64-5

Usage

Purification Methods

Recrystallise 19-hydroxy-4-androsten-3,17-dione from Me2CO/hexane or Et2O/hexane. It has UV with max at 242nm in EtOH or MeOH. The 19-acetoxy derivative has [] 26D +185o (CHCl3) and max 237.5nm in EtOH. [Ehrenstein & Dünnenberger J Org Chem 21 774 1956, Beilstein 8 IV2162.]

InChI:InChI=1/C19H26O3/c1-18-8-7-16-14(15(18)4-5-17(18)22)3-2-12-10-13(21)6-9-19(12,16)11-20/h10,14-16,20H,2-9,11H2,1H3/t14-,15-,16-,18-,19+/m0/s1

Upstream product

• 53-43-0 dehydroepiandrosterone 
• 63-05-8 Androstenedione 
• 33065-72-4 5β-androstane-3β,5,17β,19-tetraol 
• 79-15-2 N-bromoacetamide 
• 2857-45-6 3β,19-dihydroxy-5-androsten-17-one 
• 6563-83-3 6α,19-epoxyandrost-4-ene-3,17-dione 
• 853-23-6 prasterone acetate 
• 968-49-0 19-oxoandrostenedione 
• 67703-42-8 19-<(t-butyldimethylsilyl)oxy>androst-4-ene-3,17-dione 
• 3404-23-7 3β,17β,19-trihydroxyandrost-5-ene 
• 2685-64-5 5-bromo-6β,19-oxido-3β-hydroxy-5α-androstan-17-one 3-acetate 
• 20154-99-8 5-bromo-6β,19-epoxy-5α-androstane-3β,17β-diol 3-acetate 17-benzoate 
• 24870-00-6 5-bromo-6β,19-epoxy-5α-androstane-3,17-dione 
• 4968-05-2 androstane-3,5-dien-17-one-3β-ol acetate 

Downstream Products

• 54201-84-2 C₂₄H₃₄O₅ 
• 60966-54-3 1,3-dihydroxy-estra-1,3,5⁽¹⁰⁾-trien-17-one 
• 233768-82-6 19-(tert-butyldiphenylsiloxy)-4-androstene-3,17-dione 
• 2135-57-1 10β-Hydroperoxy-Δ⁴-oestren-3,17-dion 
• 59877-74-6 ((8R,9S,10S,13S,14S)-13-methyl-3,17-dioxo-1,2,3,6,7,8,9,11,12,13,14,15,16,17-tetradecahydro-10H-cyclopenta[a]phenanthren-10-yl)methyl 4-methylbenzenesulfonate 
• 1393446-35-9 3,19-epoxy-3-methoxy-5α-androstan-17β-ol 
• 2026-82-6 19-hydroxydihydrotestosterone 
• 152-43-2 quinestrol 
• 1169-79-5 quinestradol 
• 39791-20-3 nilestriol 
• 1624-63-1 estrone 3-cyclohexyl ether 
• 1624-62-0 estrone 3-methyl ether 
• 56614-59-6 14-dehydroequilenin-3-methylether 
• 33760-56-4 14-dehydro-17β-dihydroequilenin-3-methylether 

Relevant academic research and scientific papers

Chloroiron(III)-5,10,15,20-tetraarylporphinate/N-methylimidazole catalyzed oxidation of androst-4-en-3,17-dione by cumene hydroperoxide

The oxidation of androst-4-en-3,17-dione with cumene hydroperoxide, catalyzed by chloroiron(III)-5,10,15,20-tetraarylporphinate/N-methyl-imidazole systems, was studied under different reaction conditions. The chloroiron(III)-5,10,15,20-tetra(2,6-dichlorophenyl)porphinate/N-methy limidazole system in dichloromethane was found to be the most effective system for the aromatization of the A ring of androst-4-en-3,17-dione.

Kinetic solvent isotope effect in steady-state turnover by CYP19A1 suggests involvement of Compound 1 for both hydroxylation and aromatization steps

CYP19A1, or human aromatase catalyzes the conversion of androgens to estrogens in a three-step reaction through the formation of 19-hydroxy and 19-aldehyde intermediates. While the first two steps of hydroxylation are thought to proceed through a high-valent iron-oxo species, controversy exists surrounding the identity of the reaction intermediate that catalyzes the lyase and aromatization reaction. We investigated the kinetic isotope effect on the steady-state turnover of Nanodisc-incorporated human CYP19A1 to explore the mechanisms of this reaction. Our experiments reveal a significant (～2.5) kinetic solvent isotope effect for the C10-C19 lyase reaction, similar to that of the first two hydroxylation steps (2.7 and 1.2). These data implicate the involvement of Compound 1 as a reactive intermediate in the final aromatization step of CYP19A1.

STEROID DERIVATIVE REGULATORS, METHOD FOR PREPARING THE SAME, AND USES THEREOF

The present invention relates to steroid derivative regulators, a method for preparing the same, and uses thereof. Specifically, the present invention relates to a compound as shown in formula (I), a preparation method therefor, a pharmaceutical composition containing the compound, and uses thereof as a regulator of GABA A receptor for treating depression, convulsion, Parkinson's disease, and nervous system diseases, wherein the substituents of the formula (I) are as defined in the description.

19 Hydroxylated cortisone derivative and preparation method 19 - hydroxyl androstenedione (by machine translation)

The invention discloses 19 hydroxylated cortisone derivatives and a preparation method, namely 19 - hydroxyandrostenedione. Belong to organic synthesis and pharmacy field. To the invention, 19 - hydroxyl group can be used as a raw material, 19 - hydroxyl can be supported in a plurality of groups under the action of hydrogen peroxide, trimethyl iodosilane, palladium carbon, dichloro dicyanobenzene quinone, iodobenzene, sodium borohydride, sodium periodate and the like respectively. 19 - hydroxyl can be supported to 19 - respectively. B ring can be supported by structural modification 17. 21 And/or 19-position hydroxyl groups are substituted; cleavage 19 - hydroxyl groups may support many loose side chains. The preparation method of the essential intermediate 19 - hydroxyandrostenedione synthesized by the norethindrone contraceptive is greatly improved, and the drug production cost. (by machine translation)

A biocatalytic hydroxylation-enabled unified approach to C19-hydroxylated steroids

Steroidal C19-hydroxylation is pivotal to the synthesis of naturally occurring bioactive C19-OH steroids and 19-norsteroidal pharmaceuticals. However, realizing this transformation is proved to be challenging through either chemical or biological synthesis. Herein, we report a highly efficient method to synthesize 19-OH-cortexolone in 80% efficiency at the multi-gram scale. The obtained C19-OH-cortexolone can be readily transformed to various synthetically useful intermediates including the industrially valuable 19-OH-androstenedione, which can serve as a basis for synthesis of C19-functionalized steroids as well as 19-nor steroidal drugs. Using this biocatalytic C19-hydroxylation method, the unified synthesis of six C19-hydroxylated pregnanes is achieved in just 4 to 9 steps. In addition, the structure of sclerosteroid B is revised on the basis of our synthesis.

Preparation method of 19-demethylation-4-androstenedione

The invention discloses a preparation method of 19-demethylation-4-androstenedione and belongs to the technical field of medical intermediate processing. The preparation method comprises the following steps: (1) carrying out esterification reaction; (2) carrying out ketalation; (3) carrying out reduction reaction; (4) carrying out hydrolysis reaction; (5) carrying out esterification reaction; (6) carrying out addition reaction; (7) carrying out cyclization and hydrolysis reaction; (8) carrying out oxidation, dechloridation and ring-opening reaction; and (9) carrying out oxidation and decarboxylation reaction. The preparation method disclosed by the invention has the advantages that environmental pollution is small, usage amounts of a solvent and water are smaller, temperature sensitivity is low, control is easy, and yield is high; a chlorinating agent is adopted, so that reaction yield is increased; 1,3-dichloro-5,5-dimethylhydantoin is adopted, so that the reaction yield is further increased; and sodium hydrogen carbonate is adopted, so that final decarboxylic reaction yield is increased, and external standards and appearance of a product can be improved.

19-oxygenated steroids as therapeutic agents

The present invention provides compounds and methods of inducing a variety of therapeutic responses in a subject in need of such treatment. The method includes administering a compound of Formula (I) STR1 wherein R1 -R7 are as defined in the specification; and wherein said compound of Formula (I) is ethylenically unsaturated at a set of locations selected from the group consisting of (a) between C4 and C5 ; (b) both between C3 and C4 and between C5 and C6 ; (c) between C5 and C6 ; (d) both between C4 and C5 and between C6 and C7 ; (e) both between C3 and C4 between C5 and C6 and between C7 and C8 ; (f) both between C4 and C5 and between C7 and C8 ; and (g) both between C5 and C6 and between C7 and C8. The compounds of Formula (I) are administered in an amount effective to induce the desired therapeutic response.

Evidance for a New Pathway in the Microbial Conversion of 3β-Acetoxycholest-5-en-19-ol into Estrone

Incubation of 3β-acetoxycholest-5-en-19-ol 1 with Moraxella sp. gave three neutral metabolites 19-hydroxy-5α-androst-1-ene-3,17-dione 3, 19-hydroxyandrost-4-ene-3,17-dione 4 and 9α,19-dihydroxyandrost-4-en-3,17-dione 5 besides estrone 2.Hitherto, the metabolite 3 was unknown.Acidic metabolites were not found.Time course, resting cell and cell-free experiments clearly suggest: (a) complete removal of the C17 side chain takes place prior to the aromatisation of A ring in 2. (b) The noninvolvement of C22 phenolic acids as intermediates in the degradative sequence from 1 to 2. (c) Partially purified steroid 1,2-dehydrogenase readily converts the neutral metabolite 4 into estrone 2 and formaldehyde in the presence of phenazine methosulfate, an artificial electron acceptor.