(E)-3-(2-chloro-4-((3-(2,6-dichlorophenyl)-5-isopropylisoxazol-4-yl)methoxy)styryl)benzoic acid

Base Information

• Chemical Name: (E)-3-(2-chloro-4-((3-(2,6-dichlorophenyl)-5-isopropylisoxazol-4-yl)methoxy)styryl)benzoic acid
• CAS No.: 278779-30-9
• Deprecated CAS: 292047-56-4
• Molecular Formula: C₂₈H₂₂Cl₃NO₄
• Molecular Weight: 542.846
• European Community (EC) Number: 631-072-7
• UNII: SR225WUZ0H
• DSSTox Substance ID: DTXSID101017083
• Nikkaji Number: J1.383.256K
• Wikidata: Q27077943
• Pharos Ligand ID: H765T5R2ZN93
• ChEMBL ID: CHEMBL318457
• Mol file: 278779-30-9.mol

Synonyms:GW 4064;GW-4064;GW4064

Chemical Property of (E)-3-(2-chloro-4-((3-(2,6-dichlorophenyl)-5-isopropylisoxazol-4-yl)methoxy)styryl)benzoic acid

Chemical Property:

• Vapor Pressure: 0mmHg at 25°C
• Refractive Index: 1.654
• Boiling Point: 702.054 °C at 760 mmHg
• PKA: 4.13±0.10(Predicted)
• Flash Point: 378.389 °C
• PSA: 72.56000
• Density: 1.367 g/cm³
• LogP: 8.87280
• Storage Temp.: Desiccate at +4°C
• Solubility.: DMSO: soluble10mg/mL, clear
• XLogP3: 8.3
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 8
• Exact Mass: 541.061441
• Heavy Atom Count: 36
• Complexity: 742

Purity/Quality:

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

GW 4064 ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xn
• Hazard Codes: Xn
• Statements: 22-36
• Safety Statements: 26

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: CC(C)C1=C(C(=NO1)C2=C(C=CC=C2Cl)Cl)COC3=CC(=C(C=C3)C=CC4=CC(=CC=C4)C(=O)O)Cl
• Isomeric SMILES: CC(C)C1=C(C(=NO1)C2=C(C=CC=C2Cl)Cl)COC3=CC(=C(C=C3)/C=C/C4=CC(=CC=C4)C(=O)O)Cl
• Uses: A novel nonsteroidal FXR nuclear receptor agonist A novel nonsteroidal FXR nuclear receptor agonist. GW4064 has been used:to investigate its ability to protect the livers of mice from lipopolysaccharide (LPS)-induced inflammation and apoptosisto examine its capability to inhibit mucosal injury in ileum caused by lipopolysaccharide (LPS)to treat ileal explants

Technology Process of (E)-3-(2-chloro-4-((3-(2,6-dichlorophenyl)-5-isopropylisoxazol-4-yl)methoxy)styryl)benzoic acid

There total 7 articles about (E)-3-(2-chloro-4-((3-(2,6-dichlorophenyl)-5-isopropylisoxazol-4-yl)methoxy)styryl)benzoic acid 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: 98.0%

3-(2,6-dichlorophenyl)-4-(3'-carbomethoxy-2-chloro-stilben-4-yl)-oxymethyl-5-isopropyl-isoxazole (933799-50-9) → (E)-3-(2-chloro-4-((3-(2,6-dichlorophenyl)-5-isopropylisoxazol-4-yl)methoxy)styryl)benzoic acid (1089660-72-9,278779-30-9)

Guidance literature:

With lithium hydroxide; In tetrahydrofuran; at 20 ℃; for 24h;

DOI:10.1021/jm0002127

Reference yield:

C29H24Cl3NO4 (278779-31-0) → 3-[2-[2-chloro-4-[[3-(2,6-dichlorophenyl)-5-(1-methylethyl)-4-isoxazolyl]methoxy]phenyl]ethenyl]-benzoic acid (1089660-72-9,278779-30-9)

Guidance literature:

With water; sodium hydroxide; In tetrahydrofuran; methanol; at 100 - 120 ℃; for 0.138889h; Microwave irradiation;

DOI:10.1016/j.bmcl.2009.04.047

Reference yield:

2,6-dichlorobenzaldoxime (25185-95-9) → (E)-3-(2-chloro-4-((3-(2,6-dichlorophenyl)-5-isopropylisoxazol-4-yl)methoxy)styryl)benzoic acid (1089660-72-9,278779-30-9)

Guidance literature:

Multi-step reaction with 5 steps

1.1: NCS / dimethylformamide / 1 h / 20 °C

1.2: 3.1 g / NaOMe / tetrahydrofuran; methanol / 16 h / 20 °C

2.1: 93 percent / DIBAL-H / tetrahydrofuran / 16 h / 20 °C

3.1: 63 percent / TPP; DIAD / CH₂Cl₂ / 4 h / 20 °C

4.1: 86 percent / NaH / tetrahydrofuran / 5 h / 20 °C

5.1: 98 percent / aq. LiOH / tetrahydrofuran / 24 h / 20 °C

With lithium hydroxide; N-chloro-succinimide; di-isopropyl azodicarboxylate; thiamine diphosphate; sodium hydride; diisobutylaluminium hydride; In tetrahydrofuran; dichloromethane; N,N-dimethyl-formamide; 1.1: Oxidation / 1.2: Condensation / 2.1: Reduction / 3.1: Mitsunobu reaction / 4.1: Horner-Emmons reaction / 5.1: Hydrolysis;

DOI:10.1021/jm0002127

upstream raw materials:

3-(2,6-dichlorophenyl)-4-(3'-carbomethoxy-2-chloro-stilben-4-yl)-oxymethyl-5-isopropyl-isoxazole

2,6-dichlorobenzaldoxime

2,6-dichlorobenzaldehyde

[3-(2,6-dichlorophenyl)-5-(propan-2-yl)-1,2-oxazol-4-yl]methanol

Downstream raw materials:

(E)-2-methoxy-2-oxoethyl 3-(2-chloro-4-((3-(2,6-dichlorophenyl)-5-isopropylisoxazol-4-yl)methoxy)styryl)benzoate

(E)-3-(2-chloro-4-((3-(2,6-dichlorophenyl)-5-isopropylisoxazol-4-yl)methoxy) styryl)benzohydrazide

Refernces

• 1、 -. "Assays for ligands for nuclear receptors". Page/Page column 16. . Retrieved 2010/11/30.