1093-91-0

Usage

Uses

Used in Pharmaceutical Industry:
(16α-bromine)-3α-Dehydroepiandrosterone is used as an intermediate for the production of testosterone and related derivatives. Its role in the synthesis process is crucial for creating various medications that address hormonal imbalances and other medical conditions.
Used in Steroid Production:
In the field of steroid production, (16α-bromine)-3α-Dehydroepiandrosterone is utilized as a key compound in the manufacturing of anabolic steroids and other related steroidal substances. Its chemical properties allow for the efficient creation of these compounds, which have various applications in medicine and sports.
Used in Research and Development:
(16α-bromine)-3α-Dehydroepiandrosterone is also employed in research and development settings, where it is used to study the structure and function of steroid hormones. This knowledge can lead to the development of new drugs and therapies for a range of medical conditions.
Used in Quality Control and Analysis:
Due to its specific chemical properties, (16α-bromine)-3α-Dehydroepiandrosterone is used in quality control and analysis processes within the pharmaceutical industry. It helps ensure the purity and potency of final products, contributing to the overall safety and efficacy of medications.

Upstream product

• 53-43-0 dehydroepiandrosterone 
• 74644-60-3 16β-bromo-3β-hydroxy-5-androsten-17-one 
• 853-23-6 prasterone acetate 
• 24335-49-7 3β-acetoxy-16α-bromoandrost-5-en-17-one 
• 53-43-0 dehydroepiandrosterone 

Downstream Products

• 1159-66-6 3β,17β-dihydroxyandrost-5-en-16-one 
• 1232-73-1 16α-hydroxy dehydroepiandrosterone 
• 74644-60-3 16β-bromo-3β-hydroxy-5-androsten-17-one 
• 1159-66-6 (R)-3,17-Dihydroxy-10,13-dimethyl-1,2,3,4,7,8,9,10,11,12,13,14,15,17-tetradecahydro-cyclopenta[a]phenanthren-16-one 
• 571-05-1 androst-5-en-3β-ol-16,17-dione 
• 133522-45-9 14β-androst-5-ene-3β,17α-diyl 3-acetate 17-p-toluenesulfonate 
• 53-43-0 3β-hydroxy-14β-androst-5-en-17-one 

Relevant academic research and scientific papers

Synthesis and biological evaluation of 3β-androsta-5,8(14),15-trien-17-one derivatives as potential anticancer agents

A novel and operationally simple method for highly efficient synthesis of promising anti-cancer 3β-hydroxy-16-arylandrosta-5,8(14),15-trien-17-ones was reported. Compounds were tested for their cytotoxic activities against A549, SKOV3, MKN-45 and MDA-MB-4

SYNTHESIS OF 16α-3H ANDROGEN AND ESTROGEN SUBSTRATES FOR 16α-HYDROXYLASE

The synthesis of 16α-3H androgens and estrogens is described. 1-(3H)-Acetic acid in the presence of zinc dust reacts with 16α-bromo-17-ketosteroids to produce 16α-3H-17-ketosteroids.This chemical reaction was used to prepare 16α-3H-dehydroepiandrosterone (I) and 16α-3H-estrone acetate (XI) from 16α-bromo-dehydroepiandrosterone (X) and from 16α-bromo-estrone acetate (XII), respectively.Using appropriate microbiological techniques, it was possible to convert these radiolabelled substrates into 16α-3H-androstenedione (II) and 16α-3H-estradiol-17β (VII). 16α-3H-Estrone (VI) was obtained by the chemical hydrolysis of 16α-3H-estrone acetate.The label distribution as determined by microbiological 16α-hydroxylations indicated a specific labelling of 77percent for androgens and 65percent for estrogens in the 16α position.These substrates can be used for measuring the 16α hydroxylase activity, an important step in the biosynthesis of estriol (VIII) and estetrol (IX).

Synthesis and anti-gastric cancer activity evaluation of novel triazole nucleobase analogues containing steroidal/coumarin/quinoline moieties

A series of novel triazole nucleobase analogues containing steroidal/coumarin/quinoline moieties have been synthesized based on copper-catalyzed azide-alkyne cycloaddition (CuAAC). The anti-cancer activity of the new triazole nucleobase analogues was stud

Design, synthesis and evaluation of novel 16-imidazolyl substituted steroidal derivatives possessing potent diversified pharmacological properties

As a part of our investigations into the structural-activity relationship studies of a novel class of medicinally active 16-substituted steroids, several new 16-imidazolyl substituted steroidal derivatives have been synthesized and pharmacologically evaluated in the current study. The new steroidal analogues 5, 6, 8, 9, 11 and 12 exhibited moderate cytotoxic effects in sixty cancer cell lines derived from nine cancers types. The imidazolyl substituted steroidal derivatives 6 (DPJ-RG-1241) and 7 (RB-401) were obtained as the powerful inhibitors of aromatase with IC50 = 0.18 μM and IC50 = 0.168 μM, respectively, approximately 1.2 and 1.4 times more potent in comparison to standard drug exemestane. The bis-quaternary steroids 13 and 14 displayed potent skeletal muscle relaxant properties. An affinity constant of 0.007 μM was observed for compound 14 on frog rectus abdominis muscle preparation and 13 displayed a very high anticholinesterase activity K i = 25 nM, approximately 115-fold higher in comparison to standard drug galanthamine (Ki = 2.9 μM).

Dehydroepiandrosterone derived imidazolium salts and their antimicrobial efficacy

Hybrid molecules consisting of steroid-imidazolium salts reveal interesting biological properties, especially regarding antimicrobial activities. Novel dehydroepiandrosterone derived imidazolium salts (11 salts) with side chains of different lengths were obtained in an efficient and straightforward synthetic route. Antimicrobial properties of new salts were examined by determining their minimum inhibitory concentrations (MICs). They were studied against several strains of bacteria, including clinical isolates of MRSA, and fungi. New compounds showed high activity against Gram-positive bacteria and Candida albicans as well as good compatibility with the representatives of the host cells when applied at concentrations corresponding to MIC value. The studies indicated high antimicrobial efficacy of imidazolium salts against the above-mentioned microorganisms with low hemolytic activity at a concentration that restricts the growth of the microorganisms. The interference of salts with the immune defense system, the influence on the biological activity of monocytes/macrophages measured by their viability and metabolic activity was also studied. The new compounds have shown immunoprotective properties.

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.

NOVEL SERIES OF IMIDAZOLYL SUBSTITUTED STEROIDAL AND INDAN-1-ONE DERIVATIVES

The present invention provides a novel series of imidazolyl substituted steroidal and indan-1-one derivatives and salts thereof having the following general structural formulae (A and B)

Novel components of the human metabolome: The identification, characterization and anti-inflammatory activity of two 5-androstene tetrols

Two natural 5-androstene steroid tetrols, androst-5-ene-3β,7β, 16α,17β-tetrol (HE3177) and androst-5-ene-3α,7β,16α, 17β-tetrol (HE3413), were discovered in human plasma and urine. These compounds had significant aqueous solubility, did not bind or transactivate steroid-binding nuclear hormone receptors, and were not immunosuppressive in murine mixed-lymphocyte studies. Both compounds appear to be metabolic end products, as they were resistant to primary and secondary metabolism. Both were orally bioavailable, and were very well tolerated in a two-week dose-intensive toxicity study in mice. Anti-inflammatory properties were found with exogenous administration of these compounds in rodent disease models of multiple sclerosis, lung injury, chronic prostatitis, and colitis.

NOVEL SERIES OF IMIDAZOLYL SUBSTITUTED STEROIDAL AND INDAN-1-ONE DERIVATIVES

The present invention provides a novel series of imidazolyl substituted steroidal and indan-1-one derivatives and salts thereof having the following general structural formulae (A and B)

DRUGS AND USES

The invention relates to methods to treat specified clinical disorders such as hyperglycemia, type 2 diabetes, arthritis and multiple sclerosis. The invention also provides methods to identify and characterize drugs, which are characterized in part by eliciting a variable biologic or therapeutic effect on a biomolecule at one time and relative normalization of the biomolecule at another time point. Compounds include 17α-ethynylandrost-5-ene-3β,7β, 17β-triol or androst-5-ene-3β,4β, 16α, 17β-tetrol, which can be used as reference standards to facilitate assessing and characterizing such candidate drugs.