3-(4-((3-Phenoxybenzyl)amino)phenyl)propanoic acid

Base Information

• Chemical Name: 3-(4-((3-Phenoxybenzyl)amino)phenyl)propanoic acid
• CAS No.: 885101-89-3
• Molecular Formula: C22H21NO3
• Molecular Weight: 347.414
• European Community (EC) Number: 632-965-4
• UNII: 4T77GYP2CS
• ChEMBL ID: CHEMBL207881
• DSSTox Substance ID: DTXSID70237088
• Nikkaji Number: J2.945.288A
• Pharos Ligand ID: N7SA8ZVAG8UY
• Wikidata: Q27077960
• Mol file: 885101-89-3.mol

Synonyms:GW9508

Chemical Property of 3-(4-((3-Phenoxybenzyl)amino)phenyl)propanoic acid

Chemical Property:

• Vapor Pressure: 0mmHg at 25°C
• Boiling Point: 538.439°C at 760 mmHg
• Flash Point: 279.438°C
• PSA: 58.56000
• Density: 1.223g/cm³
• LogP: 5.18120
• Storage Temp.: Store at RT
• Solubility.: DMSO: >20mg/mL
• XLogP3: 4.7
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 8
• Exact Mass: 347.15214353
• Heavy Atom Count: 26
• Complexity: 414

Purity/Quality:

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

GW9508 ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xn,N
• Hazard Codes: Xn,N
• Statements: 22-37/38-41-50/53
• Safety Statements: 26-39-60-61

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1=CC=C(C=C1)OC2=CC=CC(=C2)CNC3=CC=C(C=C3)CCC(=O)O
• Description: GW9508 (885101-89-3) is a selective agonist at the free fatty acid receptor, FFA1/4, (GPR40 and GPR120).1 Displays anti-allodynic and anti-hyperalgesic effects in mouse inflammatory and neuropathic pain models.2 Inhibits LPA-induced proliferation of DU145 and PC-3 cells.3 Decreases hepatic lipid accumulation in a high fat diet steatosis mouse model.4 Promotes brown adipose tissue thermogenesis.5
• Uses: GW9508 is a GPR40 full agonist, used to regulate glucose in rats. Can be applied to the treatment of diabetes type 2. GPR120 selective and potent agonist also used in the treatment of diabetes type 2 due to GPR120’s ability to mediate GLP-1 secretion, insulin sensitization and anti-obesity effects. GW9508, a selective FFA1/GPR40 agonist, may be used to differentiate and characterize the free fatty acid receptor FFA1/GPR40. GW9508 is used to study the role of FFA1/GPR40 receptors in processes such as the free fatty acid enhancement of glucose-stimulated insulin release and type 2 diabetes. GW9508 is used to study the process by which FFA1/GPR40 receptors protect from ovariectomy-induced bone loss in vivo though inhibition of osteoclast differentiation and suppress complete Freund′s adjuvant (CFA)-Induced inflammatory chronic pain.

Technology Process of 3-(4-((3-Phenoxybenzyl)amino)phenyl)propanoic acid

There total 2 articles about 3-(4-((3-Phenoxybenzyl)amino)phenyl)propanoic 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: 86.0%

3-(4-aminophenyl)propionic acid (2393-17-1) + 3-Phenoxybenzaldehyde (39515-51-0) → 4-[[(3-phenoxyphenyl)methyl]amino]benzenepropranoic acid (885101-89-3)

Guidance literature:

3-(4-aminophenyl)propionic acid; 3-Phenoxybenzaldehyde; In 1,2-dichloro-ethane; at 100 ℃; for 0.166667h; microwave irradiation;

With sodium tris(acetoxy)borohydride; In 1,2-dichloro-ethane; at 20 ℃; for 1h;

With water; In 1,2-dichloro-ethane;

Reference yield:

3-(4-nitrophenyl)propionic acid (16642-79-8) + 3-Phenoxybenzaldehyde (39515-51-0) → 4-[[(3-phenoxyphenyl)methyl]amino]benzenepropranoic acid (885101-89-3)

Guidance literature:

Multistep reaction;

DOI:10.1016/j.bmcl.2006.12.084

Reference yield:

4-[[(3-phenoxyphenyl)methyl]amino]benzenepropranoic acid (885101-89-3) + 3-azidopropylamine (88192-19-2) → C25H27N5O2

Guidance literature:

With 1,1'-carbonyldiimidazole; In dichloromethane;

upstream raw materials:

3-(4-aminophenyl)propionic acid

3-Phenoxybenzaldehyde

3-(4-nitrophenyl)propionic acid

Refernces

• 1、 Tikhonova, Irina G.,Chi, Shing Sum,Neumann, Susanne,Thomas, Craig J.,Raaka, Bruce M.,Costanzi, Stefano,Gershengorn, Marvin C.. "Bidirectional, iterative approach to the structural delineation of the functional "chemoprint" in GPR40 for agonist recognition". . p. 2981 - 2989. Retrieved 2007.
• 2、 Garrido, Dulce M.,Corbett, David F.,Dwornik, Kate A.,Goetz, Aaron S.,Littleton, Thomas R.,McKeown, Steve C.,Mills, Wendy Y.,Smalley Jr., Terrence L.,Briscoe, Celia P.,Peat, Andrew J.. "Synthesis and activity of small molecule GPR40 agonists". . p. 1840 - 1845. Retrieved 2007/10/03.