963-74-6

Usage

Uses

Used in Pharmaceutical Industry:
5ALPHA-ANDROSTAN-17-ONE is used as a research compound for studying its potential role in the regulation of stress response, mood, and various physiological processes. It aids in understanding the underlying mechanisms of stress, anxiety, and mood disorders, as well as its potential as a biomarker for neurological and psychiatric conditions.
Used in Sports Nutrition Industry:
5ALPHA-ANDROSTAN-17-ONE is used as a dietary supplement for improving performance and muscle strength. It is believed to enhance athletic performance by increasing muscle mass and strength, although further research is needed to confirm its efficacy and safety.
Used in Research and Development:
5ALPHA-ANDROSTAN-17-ONE is used as a key compound in research and development for the discovery of new therapeutic agents targeting stress, anxiety, and mood disorders. Its role as a precursor to androgen and estrogen hormones makes it a valuable tool for investigating the interplay between hormonal balance and mental health.
Used in Diagnostics:
5ALPHA-ANDROSTAN-17-ONE has potential applications in diagnostics as a biomarker for certain neurological and psychiatric disorders. Its measurement in biological samples can provide insights into the presence and severity of specific conditions, guiding diagnosis and treatment strategies.
Used in Hormone Replacement Therapy:
Although not explicitly mentioned in the provided materials, 5ALPHA-ANDROSTAN-17-ONE, being a metabolite of testosterone and dihydrotestosterone, could potentially be used in hormone replacement therapy to address hormonal imbalances and related health issues. Further research would be required to explore its suitability and effectiveness in this context.

InChI:InChI=1/C19H30O/c1-18-11-4-3-5-13(18)6-7-14-15-8-9-17(20)19(15,2)12-10-16(14)18/h13-16H,3-12H2,1-2H3/t13-,14+,15+,16+,18+,19+/m1/s1

Upstream product

• 1225-43-0 10,13-Dimethyl-hexadecahydro-cyclopenta[a]phenanthren-17-ol 
• 1225-43-0 (5R,8R,9S,10S,13S,14S,17S)-10,13-Dimethyl-hexadecahydro-cyclopenta[a]phenanthren-17-ol 
• 481-21-0 cholestane 
• 848-62-4 allopregnan-20-one 
• 14639-79-3 5α-androst-2-en-17-one 
• 1912-63-6 androsta-3,5-dien-17-one 
• 481-20-9 5β-cholestane 
• 846-46-8 androstanedione 
• 50633-62-0 3β,4β-diacetoxyandrost-5-en-17-one 
• 95975-21-6 (5R,8R,9S,10S,13S,14S)-10,13-Dimethyl-hexadecahydro-cyclopenta[a]phenanthren-17-ol 
• 148773-59-5 3α-(phenylthio)androstan-17-one 
• 158299-72-0 Acetyl-thiocarbamic acid O-((3R,5S,8R,9S,10S,13S,14S)-10,13-dimethyl-17-oxo-hexadecahydro-cyclopenta[a]phenanthren-3-yl) ester 
• 35494-02-1 17β-hydroxy-5α-androstan-16-one 
• 25846-17-7 16α-hydroxy-5α-androstan-17-one 

Downstream Products

• 1225-43-0 (5R,8R,9S,10S,13S,14S,17S)-10,13-Dimethyl-hexadecahydro-cyclopenta[a]phenanthren-17-ol 
• 1035-62-7 17-(hydroxyimino)-5α-androstane 
• 4321-14-6 5α-Androstan-17-on-p-toluolsulfonylhydrazon 
• 2466-25-3 17a-oxa-D-homo-5α-androstan-17-one 
• 1236-49-3 5α-androstan-17β-acetate 
• 25848-69-5 3beta-7beta-Dihydroxy-5alpha-androstane-17-one 
• 7801-12-9 3α,11α-dihydroxy-5α-androstan-17-one 
• 49643-02-9 6α,11α-dihydroxy-5α-androstan-17-one 
• 25830-99-3 16-benzylidene-5α-androstan-17-one 
• 17291-41-7 17.17-Bis--5α-androstan 
• 438-22-2 (5α)-androstane 
• 17291-32-6 5α-androstan-17β-yl-4-toluenesulfonate 
• 127995-38-4 5α,17βH-pregnan-17-ol 
• 19037-37-7 (5α)androstanol-17α 

Relevant academic research and scientific papers

Defunctionalization of sp3 C–Heteroatom and sp3 C–C Bonds Enabled by Photoexcited Triplet Ketone Catalysts

A general strategy for enabling a light-induced defunctionalization of sp3 C–heteroatom and sp3 C–C bonds with triplet ketone catalysts and bipyridine additives is disclosed. This protocol is characterized by its broad scope without recourse to transition metal catalysts or stoichiometric exogeneous reductants, thus offering a complementary technique for activating σ sp3 C–C(heteroatom) bonds. Preliminary mechanistic studies suggest that the presence of 2,2′-bipyridines improves the lifetime of ketyl radical intermediates.

Two crystallographic forms and the absolute structure of 5α,14α-androstane

5α,14α-Androstane (C19H32) crystallizes in two different polymorphic forms in the same vapor diffusion experiment. The major form (Form I) crystallizes as thin plates in the space group P21, with Z = 4. These plates are twinned along a long c axis of length 43?? and readily suffer from radiation damage when diffracted. The minor form (Form II) crystallizes as fine needles in the space group P212121, Z = 3. In the minor form, 5α,14α-androstane cocrystallizes with 5α,14α-androstan-17-one, an oxidation product of 5α,14α-androstane. The presence of 5α,14α-androstan-17-one in the minor form of the crystals was confirmed by HR-MS. Form II can be crystallized as a pure form without the ketone impurity using a different solvent system. High level density functional theory (DFT) lattice free energy calculations were performed and show that both pure forms are isoergic within the estimated error of the calculations.

Development of Selective Steroid Inhibitors for the Glucose-6-phosphate Dehydrogenase from Trypanosoma cruzi

Chagas disease is a parasitic infection affecting millions of people across Latin America, imposing a dramatic socioeconomic burden. Despite the availability of drugs, nifurtimox and benznidazole, lack of efficacy and incidence of side-effects prompt the identification of novel, efficient, and affordable drug candidates. To address this issue, one strategy could be probing the susceptibility of Trypanosoma parasites toward NADP-dependent enzyme inhibitors. Recently, steroids of the androstane group have been described as highly potent but nonselective inhibitors of parasitic glucose-6-phosphate dehydrogenase (G6PDH). In order to promote selectivity, we have synthesized and evaluated 26 steroid derivatives of epiandrosterone in enzymatic assays, whereby 17 compounds were shown to display moderate to high selectivity for T. cruzi over the human G6PDH. In addition, three compounds were effective in killing intracellular T. cruzi forms infecting rat cardiomyocytes. Altogether, this study provides new SAR data around G6PDH and further supports this target for treating Chagas disease.

Method for hydrogenolysis of halides

The invention discloses a method for hydrogenolysis of halides. The invention discloses a preparation method of a compound represented by a formula I. The preparation method comprises the following step: in a polar aprotic solvent, zinc, H2O and a compound represented by a formula II are subjected to a reaction as shown in the specification, wherein X is halogen; Y is -CHRR or R; hydrogenin H2O exists in the form of natural abundance or non-natural abundance. According to the preparation method, halide hydrogenolysis can be simply, conveniently and efficiently achieved through a simple and mild reaction system, and good functional group compatibility and substrate universality are achieved.

Dehalogenative Deuteration of Unactivated Alkyl Halides Using D2O as the Deuterium Source

The general dehalogenation of alkyl halides with zinc using D2O or H2O as a deuterium or hydrogen donor has been developed. The method provides an efficient and economic protocol for deuterium-labeled derivatives with a wide substrate scope under mild reaction conditions. Mechanistic studies indicated that a radical process is involved for the formation of organozinc intermediates. The facile hydrolysis of the organozinc intermediates provides the driving force for this transformation.

2-Iodoxybenzoic Acid Tosylates: the Alternative to Dess–Martin Periodinane Oxidizing Reagents

Two powerful hypervalent iodine(V) oxidants, DMP-OTs (1-tosyloxy-1,1-diacetoxy-1H-1λ5-benzo[d][1,2]iodoxol-3-one) and IBX-OTs (1-tosyloxy-1-oxo-1H-1λ5-benzo[d][1,2]iodoxol-3-one) show high reactivity in the oxidation of structurally complex primary and secondary alcohols, which are highly functionalized polyketide or terpene fragments or steroids. The yields of the corresponding carbonyl compounds are even higher for the protocol that uses pyridine as additive. The oxidations proceed very rapidly at room temperature leaving the protective groups and π-systems intact and affording the corresponding carbonyl compounds in good to excellent yields. Moreover, IBX-OTs is an efficient reagent for the oxidative dehydrogenation of steroidal alcohols to the corresponding enones. (Figure presented.).

Aqueous reduction of iodosteroids to deoxysteroids

A new method for the reduction of iodosteroids to deoxysteroids has been developed using Zn, HCOOH and a catalytic amount of Aliquat 336 in water. In total, 13 iodosteroids were reduced in good to excellent yields. The higher solubilities of the substrates lead to the faster reactions, and the aqueous reaction was efficiently accelerated by granular polytetrafluoroethylene. The advantage of the aqueous system over eight organic solvents has also been demonstrated.

Direct organocatalytic stereoselective transfer hydrogenation of conjugated olefins of steroids

Kinetically controlled and organocatalytic syn-selective transfer hydrogenation has been successfully demonstrated for the reduction of the enone functional group of various steroids. Herein, diastereoselective synthesis of many 5β-steroids have been reported through organocatalysis, which have broad medicinal and pharmaceutical applications. The mechanistic studies and the selectivity of the products clearly indicated that the catalyst 1b·d-CSA is mild enough to activate the various chiral cyclic enones through iminium ion formation during the organocatalytic transfer hydrogenations with Hantzsch ester 2a as a hydrogen source. Further, clear evidence for the selective formation of intermediate iminium species [I]+ have been characterized through on-line monitoring of controlled experiments by NMR and ESI-HRMS analyses.

PROGESTERONE RECEPTOR ANTAGONISTS AND USES THEREOF

The present invention relates to a compound of formula (I): for its use as progesterone receptor antagonist, in particular for its use for the prevention and/or the treatment of cancer or uterine pathologies.

Efficient chemoselective mild deprotection of S,S-and S,O-acetals and ketals with electrophilic halogens

A novel and simple method for the chemoselective deprotection of S,S- and S,O-acetals and ketals in the presence of their O,O-analogs with electrophilic halogens to their corresponding carbonyl compounds is described using N-bromosuccinimide, N-chlorosuccinimide, 2,4,4,6-tetrabromo-2,5-cyclohexen-1- one, trichlorocyanuric acid, or molecular bromine in aqueous acetonitrile. The use of these reagents in the presence of hydrated silica gel provide efficient, novel, and mild procedures for the deprotection of cyclic and acyclic O,O-, S,S-, and S,O-acetals and ketals in excellent yields in short reaction times. Copyright Taylor & Francis Group, LLC.