- Chloroiron(III)-5,10,15,20-tetraarylporphinate/N-methylimidazole catalyzed oxidation of androst-4-en-3,17-dione by cumene hydroperoxide
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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.
- Vijayarahavan,Chauhan
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- Kinetic solvent isotope effect in steady-state turnover by CYP19A1 suggests involvement of Compound 1 for both hydroxylation and aromatization steps
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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.
- Khatri, Yogan,Luthra, Abhinav,Duggal, Ruchia,Sligar, Stephen G.
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- STEROID DERIVATIVE REGULATORS, METHOD FOR PREPARING THE SAME, AND USES THEREOF
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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.
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Paragraph 0245-0246
(2020/12/22)
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- 19 Hydroxylated cortisone derivative and preparation method 19 - hydroxyl androstenedione (by machine translation)
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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)
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Paragraph 0052-0057
(2019/09/05)
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- A biocatalytic hydroxylation-enabled unified approach to C19-hydroxylated steroids
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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.
- Wang, Junlin,Zhang, Yanan,Liu, Huanhuan,Shang, Yong,Zhou, Linjun,Wei, Penglin,Yin, Wen-Bing,Deng, Zixin,Qu, Xudong,Zhou, Qianghui
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- Preparation method of 19-demethylation-4-androstenedione
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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.
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- 19-oxygenated steroids as therapeutic agents
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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.
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- Evidance for a New Pathway in the Microbial Conversion of 3β-Acetoxycholest-5-en-19-ol into Estrone
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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.
- Shankar, V. N.,Row, T. N. Guru,Madyastha, K. M.
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p. 2233 - 2236
(2007/10/02)
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- Microbiological Transformations. XIII. Transformations of 19-Nor and 19-Hydroxy Analogues of Testosterone and Androstendione by Means of Rhodotorula mucilaginosa Strain
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Preparative transformation carried out
- Dmochowska-Gladysz, Jadwiga,Tlomak, Elzbieta,Siewinski, Antoni
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- CLEAVAGE OF TERT-BUTYLDIMETHYLSILYL ETHERS BY TETRAFLUOROBORATE SALTS
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Primary and secondary alcohols can be regenerated from their corresponding tert-butylsilyl ethers by treatment with tetrafluoroborate salts.
- Metcalf, Brian W.,Burkhart, Joseph P.,Jund, Karin
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