10429-07-9

Usage

Uses

Used in Pharmaceutical Synthesis:
3β-tosyloxy-5α-androstan-17-one is used as a key intermediate in the synthesis of aminosteroids and rocuronium bromide. It plays a crucial role in the production of these drugs due to its ability to undergo specific chemical reactions that facilitate the formation of the desired pharmaceutical compounds.
Used in the Synthesis of Rocuronium Bromide:
In the field of anesthesiology, 3β-tosyloxy-5α-androstan-17-one is utilized as an intermediate for the synthesis of rocuronium bromide, an amino steroid non-depolarizing neuromuscular blocker. This drug is essential for its muscle relaxant properties during surgical procedures, allowing for better control and safety in various medical interventions.
Used in the Preparation of Antiarrhythmics:
3β-tosyloxy-5α-androstan-17-one also serves as a reagent in the preparation of androstanes, which are compounds with potential antiarrhythmic properties. These androstanes can be further modified and developed into new drugs to treat cardiac arrhythmias, offering a valuable contribution to cardiovascular medicine.

Upstream product

• 481-29-8 Epiandrosterone 
• 98-59-9 p-toluenesulfonyl chloride 
• 53-43-0 dehydroepiandrosterone 

Downstream Products

• 1164-95-0 androsterone acetate 
• 53-41-8 cis-androsterone 
• 14639-79-3 5α-androst-2-en-17-one 
• 4589-82-6 3α-Formoxy-5α-androstan-17-on 
• 104533-64-4 toluene-4-sulfonic acid ; S-(17-oxo-5α-androstan-3α-yl)-thiuronium-salt 
• 846-46-8 androstanedione 
• 1156-86-1 3α-fluoro-5αH-androstan-17-one 
• 58507-05-4 (3S,5S,8R,9S,10S,13S,14S)-3-bromo-10,13-dimethylhexadecahydro-17H-cyclopenta[a]phenanthren-17-one 
• 53512-66-6 (3R,5S,8R,9S,10S,13S,14S)-3-bromo-10,13-dimethyltetradecahydro-1H-cyclopenta[a]phenanthren-17(2H)-one 
• 148773-59-5 3α-(phenylthio)androstan-17-one 
• 21002-45-9 3α,17β-Bis-benzoylmercapto-5α-androstan 
• 14935-81-0 5α-androst-3-en-17β-ol 
• 30048-07-8 3α,4α-epoxy-5α-androstane-17-one 
• 965-67-3 2α,3α-epoxy-5α-androstan-17-one 

Relevant academic research and scientific papers

Conversion of epiandrosterone into 17β-amino-5α-androstane

A new method for synthesizing 17β-amino-5α-androstane was developed based on tigogenin. The configuration at C-17 was proved by PMR.

Vecuronium bromide and its advanced intermediates: A crystallographic and spectroscopic study

Vecuronium bromide (Piperidinium, 1-[(2β,3α,5α,16β,17β)-3,17-bis(acetyloxy)-2-(1-piperidinyl)androstan-16-yl]-1-methyl-, bromide; Norcuron) has been extensively used in anesthesiology practice as neuromuscular blocking agent since its launch on the market in 1982. However, a detailed crystallographic and NMR analysis of its advanced synthetic intermediates is still lacking. Hence, with the aim of filling this literature gap, vecuronium bromide was prepared starting from the commercially available 3β-hydroxy-5α-androstan-17-one (epiandrosterone), implementing some modifications to a traditional synthetic procedure. A careful NMR study allowed the complete assignment of the 1H, 13C, and 15N NMR signals of vecuronium bromide and its synthetic intermediates. The structural and stereochemical characterization of 2β,16β-bispiperidino-5α-androstane-3α,17β-diol, the first advanced synthetic intermediate carrying all the stereocenters in the final configuration, was described by means of single-crystal X-ray diffraction and Hirshfeld surface analysis, allowing a detailed conformational investigation.

METHODS OF ACTIVATING MICROGLIAL CELLS

The present disclosure provides methods of using compositions that inhibit SH2-containing inositol 5'-phosphatases (SHIPs) for activating microglial cells, as well as methods for using such compositions for treatment or ameliorating of neurodegenerative disorders in a subject.

Sulfoxide Reduction/C(sp3)-S Metathesis Cascade in Ionic Liquid

A sulfoxide reduction/C-S bond metathesis cascade between sulfoxides and alkyl bromides has been developed to access high-value sulfides without the use of any catalysts or bases. In this cascade, classical Kornblum oxidation is employed to reduce sulfoxides with alkyl bromides in ionic liquid. This protocol features high functional tolerance, mild conditions, promising scalability, and sustainable solvents.

NEUROACTIVE STEROIDS, COMPOSITIONS, AND USES THEREOF

Described herein are neuroactive steroids of the Formula (I): (Formula (I)) or a pharmaceutically acceptable salt thereof; wherein R1a and R1b are as defined herein. Such compounds are envisioned, in certain embodiments, to behave as GABA modulators. The present invention also provides pharmaceutical compositions comprising a compound of the present invention and methods of use and treatment, e.g., such for inducing sedation and/or anesthesia.

SHIP INHIBITION TO COMBAT OBESITY

The present invention relates to the use of SHIP1 inhibitors and pan-SHIP1/2 inhibitors in various methods, including, without limitation: (i) a method to treat obesity or reduce body fat of an obese subject; (ii) a method to limit bone development in a subject suffering from an osteopetrotic or sclerotic disease; (iii) a method to treat or prevent diabetes; (iv) a method to reduce glucose intolerance or insulin resistance; and (v) a method to lower cholesterol.

In vitro metabolism studies of desoxy-methyltestosterone (DMT) and its five analogues, and in vivo metabolism of desoxy-vinyltestosterone (DVT) in horses

The positive findings of norbolethone in 2002 and tetrahydrogestrinone in 2003 in human athlete samples confirmed that designer steroids were indeed being abused in human sports. In 2005, an addition to the family of designer steroids called 'Madol' [also known as desoxy-methyltestosterone (DMT)] was seized by government officials at the US-Canadian border. Two years later, a positive finding of DMT was reported in a mixed martial arts athlete's sample. It is not uncommon that doping agents used in human sports would likewise be abused in equine sports. Designer steroids would, therefore, pose a similar threat to the horseracing and equestrian communities. This paper describes the in vitro metabolism studies of DMT and five of its structural analogues with different substituents at the 17α position (R￡H, ethyl, vinyl, ethynyl and 2H3-methyl). In addition, the in vivo metabolism of desoxy-vinyltestosterone (DVT) in horses will be presented. The in vitro studies revealed that the metabolic pathways of DMT and its analogues occurred predominantly in the A-ring by way of a combination of enone formation, hydroxylation and reduction. Additional biotransformation involving hydroxylation of the 17α-alkyl group was also observed for DMT and some of its analogues. The oral administration experiment revealed that DVT was extensively metabolised and the parent drug was not detected in urine. Two in vivo metabolites, derived respectively from (1) hydroxylation of the A-ring and (2) di-hydroxylation together with A-ring double-bond reduction, could be detected in urine up to a maximum of 46 h after administration. Another in vivo metabolite, derived from hydroxylation of the A-ring with additional double-bond reduction and di-hydroxylation of the 17α-vinyl group, could be detected in urine up to a maximum of 70 h post-administration. All in vivo metabolites were excreted mainly as glucuronides and were also detected in the in vitro studies.

SHIP INHIBITORS AND USES THEREOF

The present invention relates to SHIP inhibitor compounds and methods for using these compounds. In particular, the present invention discloses the following methods: (i) a method of treating graft versus host disease in a subject; (ii) a method of inhibiting a SHIP1 protein in a cell; (iii) a method of selectively inhibiting a SHIP1 protein in a cell; (iv) a method for treating or preventing graft-versus-host disease (GVHD) in a recipient of an organ or tissue transplant; (v) a method of modulating SHIP activity in a cell expressing SHIP1 or SHIP2; (vi) a method of ex vivo or in vitro treatment of transplants; (vii) a method of inhibiting tumor growth and metastasis in a subject; (viii) a method of treating a hematologic malignancy in a subject; (ix) a method of inducing apoptosis of multiple myeloma cells; (x) a method of treating multiple myeloma in a subject; (xi) a method of inhibiting the proliferation of a human breast cancer cell; and (xii) a method of treating breast cancer in a subject.

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.

Desulfurization with Nickel and Cobalt Boride: Scope, Selectivity, Stereochemistry, and Deuterium-Labeling Studies

A variety of organosulfur compounds containing alkylthio and arylthio groups underwent reductive desulfurization under notably mild conditions when treated with nickel boride, generated in situ from nickel chloride hexahydrate and sodium borohydride in methanol-THF (3:1).Phenyl, chloro, and ester groups are not reduced under these conditions, while iodo, bromo, nitrile, aldehyde, ketone, cyclopropane, and olefinic functions are reduced either completely or partially.Deuterium-labeling studies indicate that the hydrogen that is incorporated into the product originates from both the sodium borohydride and the protic solvent, suggesting the intermediacy of dihydrogen.The epimers 3α- and 3β-(phenylthio)cholestane afforded 3α- and 3β-deuteriocholestane, respectively, demonstrating that the reaction proceeds with retention of configuration.The method may thus be employed for the stereospecific preparation of deuterated products from organosulfur compounds.Arguments are presented in support of a tentative mechanism involving an oxidative addition-reductive elimination sequence via a nickel hydride intermediate.