851895-78-8

Basic information

• Product Name: (3beta)-3-(Acetyloxy)-17-(1H-benzimidazol-1-yl)androsta-5,16-diene-16-carboxaldehyde
• Synonyms: (3beta)-3-(Acetyloxy)-17-(1H-benzimidazol-1-yl)androsta-5,16-diene-16-carboxaldehyde;(3S,8R,9S,10R,13S,14S)-17-(1H-benzo[d]iMidazol-1-yl)-16-forMyl-10,13-diMethyl-2,3,4,7,8,9,10,11,12,13,14,15-dodecahydro-1H-cyclopenta[a]phenanthren-3-yl acetate;(3S,8R,9S,10R,13S)-17-(1H-benzo[d]imidazol-1-yl)-16-formyl-10,13-dimethyl-2,3,4,7,8,9,10,11,12,13,14,15-dodecahydro-1H-cyclopenta[a]phenanthren-3-yl acetate
• CAS NO: 851895-78-8
• Molecular Formula: C₂₉H₃₄N₂O₃
• Molecular Weight: 458.59186
• Mol File: 851895-78-8.mol
• Article Data: 11

Chemical Properties

• Melting Point: 227-230℃
• Appearance: /
• Density: 1.30
• CAS DataBase Reference: (3beta)-3-(Acetyloxy)-17-(1H-benzimidazol-1-yl)androsta-5,16-diene-16-carboxaldehyde(CAS DataBase Reference)
• NIST Chemistry Reference: (3beta)-3-(Acetyloxy)-17-(1H-benzimidazol-1-yl)androsta-5,16-diene-16-carboxaldehyde(851895-78-8)
• EPA Substance Registry System: (3beta)-3-(Acetyloxy)-17-(1H-benzimidazol-1-yl)androsta-5,16-diene-16-carboxaldehyde(851895-78-8)

Safety Data

• Hazardous Substances Data: 851895-78-8(Hazardous Substances Data)

Usage

General Description

The chemical compound (3beta)-3-(Acetyloxy)-17-(1H-benzimidazol-1-yl)androsta-5,16-diene-16-carboxaldehyde is a steroidal derivative that contains a benzimidazole group. It is a synthetic compound with potential biological activity and may be used in research and drug development. The molecule's structure includes a steroid backbone with an acetyloxy group at position 3 and a benzimidazole group attached at position 17, as well as a carboxaldehyde functional group at position 16. The specific properties and potential uses of this compound would depend on further research and testing.

Upstream product

• 51-17-2 benzoimidazole 
• 1865-56-1 3β-acetoxy-17-chloro-16-formylandrost-5,16-diene 

Downstream Products

• 1441046-97-4 3β-acetoxy-17-(1H-benzimidazol-1-yl)-16-(((3,4-dimethoxyphenyl)amino)methyl)-androsta-5,16-diene 
• 1441046-96-3 3β-acetoxy-17-(1H-benzimidazol-1-yl)-16-((EZ)-((3,4-dimethoxyphenyl)imino)methyl)androsta-5,16-diene 
• 1441046-92-9 3β-acetoxy-17-(1H-benzimidazol-1-yl)-16-((EZ)-(phenylimino)methyl)androsta-5,16-diene 
• 1441047-09-1 3β-(6-(cyclohex-3-enecaboxylic acid)carboxylate)-17-(1H-benzimidazol-1-yl)-androsta-5,16-diene 
• 1441047-08-0 3β-(3-(oxycarbonyl)phenylacetic acid)-17-(1H-benzimidazol-1-yl)-androsta-5,16-diene 
• 1441047-00-2 3β-tosyloxy-17-(1H-benzimidazol-1-yl)-androsta-5,16-diene 
• 1441046-98-5 3β-hydroxy-17-(1H-benzimidazol-1-yl)-16-(((3,4-dimethoxyphenyl)amino)methyl)-androsta-5,16-diene 
• 1441046-94-1 3β-hydroxy-17-(1H-benzimidazol-1-yl)-16-((phenylamino)methyl)-androsta-5,16-diene 
• 1441046-93-0 3β-acetoxy-17-(1H-benzimidazol-1-yl)-16-((phenylamino)-methyl)androsta-5,16-diene 
• 851983-85-2 Galeterone 
• 851895-79-9 3β-acetoxy-17-(1H-benzimidazol-1-yl)-androsta-5,16-diene 

Relevant articles and documents

Synthesis of Heterocyclic-Substituted Novel Hydroxysteroids with Regioselective and Stereoselective Reactions

Polyhydroxy steroids bearing the 3β,5α,6β-trihydroxy pattern were synthesized from different heterocyclic-substituted unsaturated steroid by an easy and simple method with high yields. The endocyclic double bond of thiophene-substituted and quinoline-substituted steroids were converted to the trans-diaxial diol by the regioselective and stereoselective reactions with m-chloroperoxybenzoic acid in the basic medium.

Novel dehydroepiandrosterone benzimidazolyl derivatives as 5α-reductase isozymes inhibitors

5α-R isozymes (types 1 and 2) play an important role in prostate gland development because they are responsible for intraprostatic dihydrotestosterone (DHT) levels when the physiological serum testosterone (T) concentration is low. In this study, we synthesized seven novel dehydroepiandrosterone derivatives with benzimidazol moiety at C-17, and determined their effect on the activity of 5α-reductase types 1 and 2. The derivatives with an aliphatic ester at C-3 of the dehydroepiandrosterone scaffold induced specific inhibition of 5α-R1 activity, whereas those with a cycloaliphatic ester (cyclopropyl, cyclobutyl, or cyclopentyl ring) or an alcohol group at C-3 inhibited the activity of both isozymes. Derivatives with a cyclohexyl or cycloheptyl ester at C-3 showed no inhibitory activity. In pharmacological experiments, derivatives with esters having an alcohol or the aliphatic group or one of the three smaller cycloaliphatic rings at C-3 decreased the diameter of male hamster flank organs, with the cyclobutyl and cyclopentyl esters exhibiting higher effect. With exception of the cyclobutyl and cyclopentyl esters, these compounds reduced the weight of the prostate and seminal vesicles.

Discovery and development of galeterone (TOK-001 or VN/124-1) for the treatment of all stages of prostate cancer

In our effort to discover potent and specific inhibitors of 17α-hydroxylase/17,20-lyase (CYP17), the key enzyme which catalyzes the biosynthesis of androgens from progestins, 3β-(hydroxy)-17-(1H-benzimidazole-1-yl)androsta-5,16-diene (Galeterone or TOK-001, formerly called VN/124-1) was identified as a selective development candidate which modulates multiple targets in the androgen receptor (AR) signaling pathway. This drug annotation summarizes the mechanisms of action, scientific rationale, medicinal chemistry, pharmacokinetic properties, and human efficacy data for galeterone, which has successfully completed phase II clinical development in men with castration resistant (advanced) prostate cancer (CRPC). Phase III clinical studies in CRPC patients are scheduled to begin in early 2015.