2206-20-4

Basic information

• Product Name: Cholestan-3-aMine, (3α,5α)-
• Synonyms: Cholestan-3-aMine, (3α,5α)-;3-a-aMinocholestane (3AC);3alpha-Aminocholestane;5alpha-Cholestan-3alpha-amine;3α-Aminocholestane;(3α,5α)-Cholestan-3-amine
• CAS NO: 2206-20-4
• Molecular Formula: C₂₇H₄₉N
• Molecular Weight: 387.68466
• Mol File: 2206-20-4.mol
• Article Data: 12

Chemical Properties

• Melting Point: 104.5-105.5℃ (methanol )
• Boiling Point: 160 °C(Press: 0.1 Torr)
• Appearance: /
• Density: 0.930±0.06 g/cm3(Predicted)
• PKA: 10.94±0.70(Predicted)
• CAS DataBase Reference: Cholestan-3-aMine, (3α,5α)-(CAS DataBase Reference)
• NIST Chemistry Reference: Cholestan-3-aMine, (3α,5α)-(2206-20-4)
• EPA Substance Registry System: Cholestan-3-aMine, (3α,5α)-(2206-20-4)

Safety Data

• Hazardous Substances Data: 2206-20-4(Hazardous Substances Data)

Usage

Uses

3α-Aminocholestane is a selective SH2 domain-containing inositol-5′-phosphatase 1 (SHIP1) inhibitor with an IC50 of ~2.5 μM.

Upstream product

• 80-97-7 Cholestanol 
• 3381-51-9 (3S,5S,8R,9S,10S,13R,14S,17R)-10,13-dimethyl-17-((R)-6-methylheptan-2-yl)hexadecahydro-1H-cyclopenta[a]phenanthren-3-yl methanesulfonate 
• 3381-53-1 3α-cholestanyl mesylate 
• 516-95-0 epicholestanol 
• 15067-20-6 3α-azido-5α-cholestane 
• 2735-21-9 anti-oxime of 5α-cholestan-3-one 
• 3381-52-0 3β-(toluene-4-sulfonyloxy)-5α-cholestane 
• 566-88-1 dihydrocholesterone 

Downstream Products

• 261786-55-4 N-(5α-cholestan-3α-yl)-4,4-bis(3-chloro-4-methoxy-5-methoxycarbonylphenyl)-3-butenamide 
• 85858-35-1 3α-(N-toluene-p-sulphonamido)cholestan 
• 24306-95-4 N-(5α-cholestan-3=a)-yl-formamide 
• 5457-79-4 3α-amino-5α-cholestane hydrochloride 

Relevant articles and documents

Asymmetric reductive amination of cycloalkanones, IV: Synthesis of optically active trans-3-substituted cyclohexanimes

-

Predictable Selectivity in Remote C?H Oxidation of Steroids: Analysis of Substrate Binding Mode

Predictability is a key requirement to encompass late-stage C?H functionalization in synthetic routes. However, prediction (and control) of reaction selectivity is usually challenging, especially for complex substrate structures and elusive transformations such as remote C(sp3)?H oxidation, as it requires distinguishing a specific C?H bond from many others with similar reactivity. Developed here is a strategy for predictable, remote C?H oxidation that entails substrate binding to a supramolecular Mn or Fe catalyst followed by elucidation of the conformation of the host-guest adduct by NMR analysis. These analyses indicate which remote C?H bonds are suitably oriented for the oxidation before carrying out the reaction, enabling prediction of site selectivity. This strategy was applied to late-stage C(sp3)?H oxidation of amino-steroids at C15 (or C16) positions, with a selectivity tunable by modification of catalyst chirality and metal.

Evaluation of steroidal amines as lipid raft modulators and potential anti-influenza agents

The influenza A virus (IFV) possesses a highly ordered cholesterol-rich lipid envelope. A specific composition and structure of this membrane raft envelope are essential for viral entry into cells and virus budding. Several steroidal amines were investigated for antiviral activity against IFV. Both, a positively charged amino function and the highly hydrophobic (C log P ≥ 5.9) ring system are required for IC50 values in the low μM range. An amino substituent is preferential to an azacyclic A-ring. We showed that these compounds either disrupt or augment membrane rafts and in some cases inactivate the free virus. Some of the compounds also interfere with virus budding. The antiviral selectivity improved in the series 3-amino, 3-aminomethyl, 3-aminoethyl, or by introducing an OH function in the A-ring. Steroidal amines show a new mode of antiviral action in directly targeting the virus envelope and its biological functions.