2206-20-4

Usage

Uses

Used in Pharmaceutical Industry:
Cholestan-3-aMine, (3α,5α)is used as a selective inhibitor for the SH2 domain-containing inositol-5′-phosphatase 1 (SHIP1) enzyme. The compound has an IC50 of approximately 2.5 μM, indicating its potency in inhibiting the target enzyme. This makes it a valuable tool in the development of therapeutic strategies for conditions related to the dysregulation of SHIP1 activity.
In the context of research and drug discovery, Cholestan-3-aMine, (3α,5α)can be used as a starting point for the design and synthesis of more potent and selective SHIP1 inhibitors. These inhibitors may have potential applications in the treatment of various diseases, including certain types of cancer and immune disorders, where the modulation of SHIP1 activity is believed to play a crucial role.
Additionally, the compound may also be utilized in the study of the biological functions of SHIP1 and its role in cellular signaling pathways. This can contribute to a better understanding of the underlying mechanisms of various diseases and the development of novel therapeutic approaches.

Upstream product

• 566-88-1 dihydrocholesterone 
• 3381-53-1 3α-cholestanyl mesylate 
• 516-95-0 epicholestanol 
• 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 
• 80-97-7 Cholestanol 
• 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 

Downstream Products

• 24306-95-4 N-(5α-cholestan-3=a)-yl-formamide 
• 5457-79-4 3α-amino-5α-cholestane hydrochloride 
• 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 

Relevant academic research and scientific papers

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.

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.

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.

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.

DERIVATIVES OF STEROID BENZYLAMINES, HAVING AN ANTIPARASITIC ANTIBACTERIAL, ANTIMYCOTIC AND/OR ANTIVIRAL ACTION

The present invention relates to compounds derived from steroids of the general formula (I) wherein L represents a linker and R# represents a steroid residue, the use of compounds of the general formula (I) in medicine and for the prophylaxis a

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.

CHOLESTERYLAMINES FOR THE TREATMENT AND PREVENTION OF INFECTIOUS DISEASES

The present invention relates to the use of cholesterylamines in the preparation of pharmaceutical compositions. These pharmaceutical compositions are to be used in the medical intervention of infectious diseases, in particular diseases caused by a virus or a bacterium.

Synthesis and antimicrobial evaluation of water-soluble, dendritic derivatives of epimeric 5α-cholestan-3-amines and 5α-cholestan-3-yl aminoethanoates

To examine the effect of negatively charged steroidal amphiphiles on antimicrobial activity, two pairs of epimeric, dendritic tricarboxylato amphiphiles - 4-(2-carboxyethyl)-4-[3-(5α-cholestan-3-yl)ureido]heptanedioic acid (1) and 4-(2-carboxyethyl)-4-[3-(5α-cholestan-3-yloxycarbonylmethyl)ureido]heptanedioic acid (2) - were synthesized. A broad antimicrobial screen of 11 microbes revealed that these amphiphiles only showed good activity against a methicillin-resistant isolate of Staphylococcus aureus (MRSA) and modest activity against an unrelated strain of S. aureus. The best activity, a minimal inhibitory concentration (MIC) of 27 μM, was found for the 3β epimer of 1 against MRSA.

The effects of added ammonium chloride in the reductive amination of some carbonyl compounds over Ru and Pd catalysts

The reductive amination of acetophenone, (+)-camphor, and 5α-cholestan-3-one over Ru and Pd metals as well as their carbon-supported catalysts gave corresponding amines together with alcohols as by-products. However, we found that the corresponding amines are selectively synthesized by the addition of ammonium chloride to the reaction system with depression of the formation of alcohol, as exemplified with acetophenone. Although alcohols are usually not formed over Pd with alicyclic ketones, the alcohols formation was effectively depressed over Ru in the presence of ammonium chloride. The effects of the additive on the stereoselectivity of the formation of amines are also discussed in the cases of (+)-camphor and 5α-cholestan-3-one.

Nicotinoyl azide (NCA)-mediated Mitsunobu reaction: An expedient one-pot transformation of alcohols into azides

A practical and simple method that allows preparation of azides from alcohols is described. The process involves oxyphosphonium-type activation and it is based upon the use of nicotinoyl azide (NCA), a cheap and easily accessible azide ion source.