N-[9a,11a-dimethyl-1-(6-methylheptan-2-yl)-1H,2H,3H,3aH,3bH,4H,5H,7H,8H,9H,9aH,9bH,10H,11H,11aH-cyclopenta[a]phenanthren-7-ylidene]hydroxylamine

Base Information

• Chemical Name: N-[9a,11a-dimethyl-1-(6-methylheptan-2-yl)-1H,2H,3H,3aH,3bH,4H,5H,7H,8H,9H,9aH,9bH,10H,11H,11aH-cyclopenta[a]phenanthren-7-ylidene]hydroxylamine
• CAS No.: 22033-87-0
• Molecular Formula: C27H45NO
• Molecular Weight: 399.66
• European Community (EC) Number: 896-756-1
• NCI Thesaurus Code: C174604
• Wikipedia: Olesoxime
• Mol file: 22033-87-0.mol

Synonyms:cholest-4-en-3-one, oxime;olesoxime;TRO19622

Chemical Property of N-[9a,11a-dimethyl-1-(6-methylheptan-2-yl)-1H,2H,3H,3aH,3bH,4H,5H,7H,8H,9H,9aH,9bH,10H,11H,11aH-cyclopenta[a]phenanthren-7-ylidene]hydroxylamine

Chemical Property:

• Vapor Pressure: 1.56E-12mmHg at 25°C
• Melting Point: 145-148 ºC
• Refractive Index: 1.583
• Boiling Point: 510 °C at 760 mmHg
• PKA: 12.27±0.70(Predicted)
• Flash Point: 341 °C
• PSA: 32.59000
• Density: 1.10g/cm³
• LogP: 7.85800
• Storage Temp.: −20°C
• Solubility.: DMSO: >10mg/mL
• XLogP3: 8.8
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 5
• Exact Mass: 399.350115059
• Heavy Atom Count: 29
• Complexity: 663

Purity/Quality:

98%,99%, ^*data from raw suppliers

TRO 19622 ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(C)CCCC(C)C1CCC2C1(CCC3C2CCC4=CC(=NO)CCC34C)C
• Isomeric SMILES: CC(C)CCCC(C)C1CCC2C1(CCC3C2CCC4=C/C(=N\O)/CCC34C)C
• Recent ClinicalTrials: Safety and Efficacy of TRO19622 as add-on Therapy to Riluzole Versus Placebo in Treatment of Patients Suffering From ALS
• Recent EU Clinical Trials: Multicenter, open-label, single-arm study to evaluate long term safety, tolerability, and effectiveness of 10mg/kg BID olesoxime in patients with Spinal Muscular Atrophy
• Description: TRO19622 (22033-87-0) is a neuroregenerative and neuroprotective agent acting at components of the mitochondrial permeability transition pore (MPTP).1?Rescues motor neurons from axotomy-induced cell death and promotes nerve regeneration following sciatic nerve crush in mice. Reduces ROS and NLRP3 inflammasome activation in a mouse model of intracerebral hemorrhage.2?Inhibits MPTP opening and protects neurons from apoptosis.3?Induces oligodendrocyte maturation in culture and promotes myelin regeneration?in vivo?in a rodent model.4
• Uses: TRO 19622 interacts with mitochondria proteins and is able to promote neuron survival under stress conditions. It is a potential drug for treating amyotrophic lateral sclerosis (ALS). TRO 19622 is a neuroregenerative and neuroprotective agent. This is a research product for neuroscience. TRO 19622 has been used as a mitochondrial permeability transition pore inhibitor in mouse neurons2. TRO 19622 is also known to stimulate myelin repair in rat models of demyelination3.

Technology Process of N-[9a,11a-dimethyl-1-(6-methylheptan-2-yl)-1H,2H,3H,3aH,3bH,4H,5H,7H,8H,9H,9aH,9bH,10H,11H,11aH-cyclopenta[a]phenanthren-7-ylidene]hydroxylamine

There total 2 articles about N-[9a,11a-dimethyl-1-(6-methylheptan-2-yl)-1H,2H,3H,3aH,3bH,4H,5H,7H,8H,9H,9aH,9bH,10H,11H,11aH-cyclopenta[a]phenanthren-7-ylidene]hydroxylamine which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 90.0%

Cholest-4-en-3-one (601-57-0) → cholest-4-en-3-one oxime (22033-87-0)

Guidance literature:

With hydroxylamine hydrochloride; sodium acetate; In methanol; water; at 60 ℃;

DOI:10.1021/jo9812429

Reference yield:

→ Cholesten-(4)-on-(3)-oxim (22033-87-0,66514-00-9,66538-08-7)

Guidance literature:

Cholest-4-en-3-on, Hydroxylamin-hydrochlorid, Natriumacetat, A., Δ;

Reference yield: 80.0%

cholest-4-en-3-one oxime (22033-87-0) → Cholest-4-en-3-one (601-57-0)

Guidance literature:

With benzeneseleninic anhydride; In tetrahydrofuran;

upstream raw materials:

Cholest-4-en-3-one

Downstream raw materials:

Cholest-4-en-3-one

4-aza-A-homocholest-4a-en-3-one

(5aR,5bS,7aR,8R,10aS,10bS)-5a,7a-dimethyl-8-((R)-6-methylheptan-2-yl)-4,5,5a,5b,6,7,7a,8,9,10,10a,10b,11,12-tetradecahydrocyclopenta[5,6]naphtho[1,2-d]azepin-2(3H)-one

C₃₉H₅₄NOP

Refernces

• 1、 Hutchins, Robert O.,Rao, Samala J.,Adams, Jeffrey,Hutchins, Marygail K.. "Stereoselective hydride reductions of cyclic α,β-unsaturated n-diphenylphosphinyl imines to protected allylic amines". . p. 8077 - 8080. Retrieved 2007/10/03.