28507-02-0

Basic information

• Product Name: 16-bromoepiandrosterone
• Synonyms: 16-bromoepiandrosterone
• CAS NO: 28507-02-0
• Molecular Formula: C₁₉H₂₉BrO₂
• Molecular Weight: 369.33636
• Mol File: 28507-02-0.mol

Chemical Properties

• Boiling Point: 448.6°Cat760mmHg
• Flash Point: 225.1°C
• Appearance: /
• Density: 1.309g/cm³
• Vapor Pressure: 6.24E-10mmHg at 25°C
• Refractive Index: 1.56
• CAS DataBase Reference: 16-bromoepiandrosterone(CAS DataBase Reference)
• NIST Chemistry Reference: 16-bromoepiandrosterone(28507-02-0)
• EPA Substance Registry System: 16-bromoepiandrosterone(28507-02-0)

Safety Data

• Hazardous Substances Data: 28507-02-0(Hazardous Substances Data)

Usage

Uses

Used in Bodybuilding and Athletic Performance Enhancement:
16-bromoepiandrosterone is used as a performance-enhancing supplement for its ability to increase muscle strength and growth. It is favored by bodybuilders and athletes seeking to achieve lean muscle mass and improve their physical capabilities.
Used in Fat Loss and Lean Muscle Mass Development:
16-bromoepiandrosterone is also used as a fat loss agent, helping to reduce body fat while promoting the development of lean muscle mass, which is crucial for athletes and bodybuilders aiming for a toned and defined physique.
Used in Sports Nutrition:
In the sports nutrition industry, 16-bromoepiandrosterone is used as a dietary supplement to support the goals of enhanced physical performance and body composition modification.

InChI:InChI=1/C19H29BrO2/c1-18-7-5-12(21)9-11(18)3-4-13-14(18)6-8-19(2)15(13)10-16(20)17(19)22/h11-16,21H,3-10H2,1-2H3/t11-,12-,13+,14-,15-,16+,18-,19-/m0/s1

Upstream product

• 481-29-8 Epiandrosterone 
• 1242-55-3 3β-acetoxy-16α-bromo-5α-androstan-17-one 
• 1239-31-2 3β-acetoxy-5α-androstan-17-one 
• 5717-77-1 (3β,5α)-3-hydroxyandrostan-17-one, cyclic 1,2-ethanediyl acetal 
• 53-43-0 dehydroepiandrosterone 
• 18323-34-7 (3S,5S,8R,9S,10S,13S,14S)-16-Diazo-3-hydroxy-10,13-dimethyl-hexadecahydro-cyclopenta[a]phenanthren-17-one 
• 62675-96-1 16α-bromo-17,17-ethylendioxy-5α-androstan-3β-yl acetate 
• 3674-78-0 17,17-ethylendioxy-5α-androstan-3β-yl acetate 
• 18453-92-4 (3α,5β)-3-hydroxyandrostane-16,17-dione 16-oxime 

Downstream Products

• 110043-05-5 16β-bromo-5α-androstane-3β,17β-diol 
• 94441-01-7 16α-bromo-5α-androstane-3,17-dione 
• 72005-68-6 2'-amino-(5α)-androstano[17,16-d]thiazol-3β-ol 
• 3000-34-8 16β-morpholino-3β-hydroxy-5α-androstan-17-one 
• 100702-68-9 17β-cyano-16α,17α-epoxy-5α-androstan-3β-ol 
• 10459-27-5 3β,16α-dihydroxy-5α-androstan-17-one 
• 1159-67-7 3β,16α-dihydroxy-5α-androstan-17-one 
• 321595-50-0 16β-Azido-3β-hydroxy-α-androstan-17-one 
• 1242-55-3 3β-acetoxy-16α-bromo-5α-androstan-17-one 
• 886847-73-0 16β-piperidino-3-pyrrolidino-5α-androst-2-en-17-one 
• 886847-74-1 16β-piperidino-3β-pyrrolidino-5α-androstan-17β-ol 
• 886847-75-2 16β-piperidino-3β-pyrrolidino-5α-androstan-17β-yl acetate 
• 3136-46-7 16β-piperidino-5α-androstane-3,17-dione 
• 321595-51-1 5''α-Androstano[16'',17''-5',6']pyrazino[2',3'-16,17]-5α-androstane-3β,3''β-diol 

Relevant articles and documents

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.

Preparation method of (3beta, 15alpha)-dihydroxyl-14beta-phenylamino or benzylaminoandrostane-17-ketone

The invention belongs to the field of chemical synthesis and relates to a preparation method of (3beta, 15alpha)-dihydroxyl-14beta-phenylamino or benzylaminoandrostane-17-ketone. The preparation method comprises the following steps of: utilizing natural steroid epiandrosterone as a raw material to react with copper bromide, then removing hydrogen bromide to obtain alkene, separating the obtained (3beta)-hydroxyl-androstane-14(15)-diene-17-ketone to react with MMPP, and obtaining an intermediate (3beta)-hydroxyl-14, 15-epoxy androstane-17-ketone; under the action of an acetic acid medium, usingphenylamine or benzylamine to carry out ring opening on epoxy units of the intermediate (3beta)-hydroxyl-14, 15-epoxy androstane-17-ketone, and obtaining a target compound. The product prepared by the invention has a carbonyl structure unit on a steroid rigid framework, and the structure units such as 14beta-NHPh or 14beta-NHCH2Ph and 15alpha-OH and the like play an important role in biological activity.

Steroid purine nucleoside analogue containing 1,2,3-triazole as well as preparation method and application thereof

The invention belongs to the technical field of medical chemistry and relates to a steroid purine nucleoside analogue containing 1,2,3-triazole as well as a preparation method and application thereof. The steroid purine nucleoside analogue has a following general formula: the formula is shown in the description. The steroid purine nucleoside analogue is prepared by taking 3beta-hydroxy-5alpha-androstan-17-ketone or 4-aza-5alpha-androstan-3,17-dione as a raw material through bromination, oxidization, azidation and cycloaddition reaction; the preparation method is simple and has moderate conditions; the total yield of targets reaches 75 percent or more. The compound provided by the invention has a remarkable inhibition effect on cell lines of prostatic carcinoma, gastric carcinoma and the like and a leading compound structure is provided for further research of anti-cancer medicines, so that the variety of the steroid purine nucleoside analogue is enriched.

An efficient synthesis of 3β,14β-dihydroxy-5α-androst-15-en-17-one

An efficient four-step method has been developed for the synthesis of 3β,14β-dihydroxy-5α-androst-15-en-17-one from a common androstane derivative. The X-ray crystal structures of the alkenes, the epoxide and the 14-hydroxy compound have been determined.

Novel steroid inhibitors of glucose 6-phosphate dehydrogenase

Novel derivatives of the steroid DHEA 1, a known uncompetitive inhibitor of G6PD, were designed, synthesized, and tested for their ability to inhibit this dehydrogenase enzyme. Several compounds with approximately 10-fold improved potency in an enzyme assay were identified, and this improved activity translated to efficacy in a cellular assay. The SAR for steroid inhibition of G6PD has been substantially developed; the 3β-alcohol can be replaced with 3β-H-bond donors such as sulfamide, sulfonamide, urea, and carbamate. Improved potency was achieved by replacing the androstane nucleus with a pregnane nucleus, provided a ketone at C-20 is present. For pregnan-20-ones incorporation of a 21-hydroxyl group is often beneficial. The novel compounds generally have good physicochemical properties and satisfactory in vitro DMPK parameters. These derivatives may be useful for examining the role of G6PD inhibition in cells and will assist the future design of more potent steroid inhibitors with potential therapeutic utility.

Synthesis, characterization and biological evaluation of some 16β-azolyl-3β-amino-5α-androstane derivatives as potential anticancer agents

A series of new 16β-azolyl-3β-amino-5α-androstane derivatives were synthesized and characterized. The new compounds were screened for their anticancer activity against the human cancer cell lines SW480, A549, HepG2, HeLa and SiHa in vitro using the MTT assay. The results of the in vitro study showed that a number of compounds have shown IC50 values lower than 20 μM against the five cancer cell lines.

Synthesis and neuromuscular blocking activity of 16β-piperidino epiandrosterone derivatives

This study reports the synthesis of steroidal quaternary ammonium compounds 11 and 12, with quaternary nitrogen at position 3 and 16 of the steroid nucleus in 5α-epiandrosterone series; along with their neuromuscular blocking activity using chick biventer cervicis muscle preparation. The compound 12 was found to be five times more potent than 11 in reducing twitch response to nerve stimulations, indicating the importance of extended interonium distances and 17-acetoxy function for potent antagonist activity. Birkhaeuser Boston 2006.

5 α-pregnan-20-ones and 5-pregnen-20-ones and related compounds

Compounds of the formulae: STR1 useful as anti-obesity, anti-diabetic, anti-coronary and hypolipidemic agents.

Homoandrostan-17-one and homoandrosten-17-ones

Compounds of the formula: STR1 useful as anti-cancer agents, anti-obesity agents, anti-hyperglycemic agents, anti-aging agents, anti-hyperglycemic agents and anti-autoimmune agents.

16-substituted androstanes and 16-substituted androstenes

Compounds of the formula: STR1 are useful as anti-cancer, anti-obesity, anti-diabetic, anti-coronary agents, anti-aging agents, anti-hypolipidemic agents and anti-autoimmune agents.