Avasimibe

Base Information

• Chemical Name: Avasimibe
• CAS No.: 166518-60-1
• Molecular Formula: C29H43NO4S
• Molecular Weight: 501.731
• Hs Code.: 2935009090
• UNII: 28LQ20T5RC
• DSSTox Substance ID: DTXSID80168117
• Nikkaji Number: J805.047C
• Wikipedia: Avasimibe
• Wikidata: Q27254327
• NCI Thesaurus Code: C75252
• Pharos Ligand ID: TCM1L6BJKGBV
• Metabolomics Workbench ID: 149780
• ChEMBL ID: CHEMBL101309
• Mol file: 166518-60-1.mol

Synonyms:2,6-bis(1-methylethyl)phenyl ((2,4,6-tris(1-methylethyl)phenyl)acetyl)sulfamate;avasimibe;avasimibe sodium;CI 1011;CI-1011

Chemical Property of Avasimibe

Chemical Property:

• Melting Point: 178-180° (Lee); mp 169.5-170.4° (Dozeman)
• Refractive Index: 1.529
• PKA: 1.97±0.70(Predicted)
• PSA: 80.85000
• Density: 1.072 g/cm³
• LogP: 8.75780
• Storage Temp.: room temp
• Solubility.: DMSO: ≥40mg/mL
• XLogP3: 8.2
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 10
• Exact Mass: 501.29128003
• Heavy Atom Count: 35
• Complexity: 734

Purity/Quality:

99% ^*data from raw suppliers

Avasimibe ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(C)C1=C(C(=CC=C1)C(C)C)OS(=O)(=O)NC(=O)CC2=C(C=C(C=C2C(C)C)C(C)C)C(C)C
• Uses: Avasimibe is a selective inhibitor of Cholesterol Acyltransferase 1 and CYP2C9. Avasimibe is known to induce apoptosis of glioma cell lines as a model of glioblastoma. Avasimibe has been used as an inhibitor of acyl-coenzyme A: cholesterol acyltransferase (ACAT) in Huh7.5.1 cells for testing its combination with direct-acting antivirals (DAAs) and to test its effect on lipid droplet accumulation in acidosis-adapted cancer cells. It may be used as an inhibitor of ACAT to assess cholesterol esterification in Trypanosoma cruzi.

Technology Process of Avasimibe

There total 6 articles about Avasimibe 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: 80.0%

2,4,6-triisopropylphenylacetyl chloride (52629-47-7) + sulfamate de diisopropyl-2,6 phenyle (92050-02-7) → avasimibe (166518-60-1)

Guidance literature:

With TEA; In tetrahydrofuran;

DOI:10.1021/jm960674d

Reference yield:

2,4,6-triisopropylbenzoyl chloride (57199-00-5) → avasimibe (166518-60-1)

Guidance literature:

Multi-step reaction with 6 steps

1: 98 percent / LAH

2: 97 percent / PBr₃ / diethyl ether

3: dimethylsulfoxide

4: aq. H₂SO₄

5: (COCl)2

6: 80 percent / TEA / tetrahydrofuran

With lithium aluminium tetrahydride; oxalyl dichloride; TEA; sulfuric acid; phosphorus tribromide; In tetrahydrofuran; diethyl ether; dimethyl sulfoxide;

DOI:10.1021/jm960674d

Reference yield:

[2,4,6-tris(1-methylethyl)phenyl]methanol (4276-88-4) → avasimibe (166518-60-1)

Guidance literature:

Multi-step reaction with 5 steps

1: 97 percent / PBr₃ / diethyl ether

2: dimethylsulfoxide

3: aq. H₂SO₄

4: (COCl)2

5: 80 percent / TEA / tetrahydrofuran

With oxalyl dichloride; TEA; sulfuric acid; phosphorus tribromide; In tetrahydrofuran; diethyl ether; dimethyl sulfoxide;

DOI:10.1021/jm960674d

upstream raw materials:

2,4,6-triisopropylphenylacetyl chloride

sulfamate de diisopropyl-2,6 phenyle

2,4,6-triisopropylbenzoyl chloride

[2,4,6-tris(1-methylethyl)phenyl]methanol

Refernces