3-[({4-[4-({[1-(2-Chlorophenyl)ethoxy]carbonyl}amino)-3-methyl-1,2-oxazol-5-yl]phenyl}methyl)sulfanyl]propanoic acid

Base Information

• Chemical Name: 3-[({4-[4-({[1-(2-Chlorophenyl)ethoxy]carbonyl}amino)-3-methyl-1,2-oxazol-5-yl]phenyl}methyl)sulfanyl]propanoic acid
• CAS No.: 355025-24-0
• Molecular Formula: C23H23ClN2O5S
• Molecular Weight: 474.963
• Hs Code.: 29349990
• UNII: 83W49JT69B
• DSSTox Substance ID: DTXSID90438772
• Wikidata: Q27163117
• Pharos Ligand ID: DNSWU6N6HKHS
• ChEMBL ID: CHEMBL361501
• Mol file: 355025-24-0.mol

Synonyms:3-(4-(4-((1-(2-chlorophenyl)ethoxy)carbonyl amino)-3-methyl-5-isoxazolyl) benzylsulfanyl) propanoic acid;Debio 0719;Debio 0719-425;Ki16425

Chemical Property of 3-[({4-[4-({[1-(2-Chlorophenyl)ethoxy]carbonyl}amino)-3-methyl-1,2-oxazol-5-yl]phenyl}methyl)sulfanyl]propanoic acid

Chemical Property:

• Melting Point: 59.5-60.5 °C
• Boiling Point: 623.7 °C at 760 mmHg
• PKA: 4.32±0.10(Predicted)
• Flash Point: 331 °C
• PSA: 126.96000
• Density: 1.353 g/cm³
• LogP: 6.39400
• Storage Temp.: 2-8°C
• Solubility.: DMSO: 16 mg/mL
• XLogP3: 4.5
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 7
• Rotatable Bond Count: 10
• Exact Mass: 474.1016207
• Heavy Atom Count: 32
• Complexity: 619

Purity/Quality:

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

Ki 16425 ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC1=NOC(=C1NC(=O)OC(C)C2=CC=CC=C2Cl)C3=CC=C(C=C3)CSCCC(=O)O
• Description: Lysophosphatidic acid (LPA) is a bioactive lipid mediator that signals through five distinct G protein-coupled receptors (LPA1-5). Ki16425 is a LPA receptor antagonist with selectivity for LPA1 and LPA3. It exhibits Ki values of 0.34, 6.5, and 0.93 μM for the human LPA1, LPA2, and LPA3 receptors, respectively, as determined by measuring inositol phosphate production in RH7777-transfected cells. Ki1642, at 10 μM, significantly blocks the response of a variety of cancer cell lines to LPA-induced cell migration.
• Uses: Ki 16425 has been used as a chemical inhibitor to study the regulation of LPA (lysophosphatidic acid) on LPAR(LPA receptor) subtypes. Ki16425 is a competitive, potent and reversible antagonist to LPA1, LPA2 and LPA3.

Technology Process of 3-[({4-[4-({[1-(2-Chlorophenyl)ethoxy]carbonyl}amino)-3-methyl-1,2-oxazol-5-yl]phenyl}methyl)sulfanyl]propanoic acid

There total 13 articles about 3-[({4-[4-({[1-(2-Chlorophenyl)ethoxy]carbonyl}amino)-3-methyl-1,2-oxazol-5-yl]phenyl}methyl)sulfanyl]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: 87.0%

methyl 3-({4-[4-({[1-(2-chlorophenyl)ethoxy]carbonyl}amino)-3-methyl-5-isoxazolyl] benzyl}sulfanyl)propanoate → (+/-)-Ki16425 (355025-24-0)

Guidance literature:

With lithium hydroxide monohydrate; water; In tetrahydrofuran; at 20 ℃; for 4h;

DOI:10.1016/j.bmcl.2012.05.012

Reference yield:

methyl 5-(4-(hydroxymethyl)phenyl)-3-methylisoxazole-4-carboxylate (1384485-33-9) → (+/-)-Ki16425 (355025-24-0)

Guidance literature:

Multi-step reaction with 5 steps

1: tetrachloromethane; triphenylphosphine / dichloromethane / 0.33 h / 20 - 50 °C

2: lithium hydroxide monohydrate; water / tetrahydrofuran / 19 h / 20 °C

3: diphenyl phosphoryl azide; triethylamine / toluene / 0.5 h / 120 °C

4: tetra-(n-butyl)ammonium iodide; triethylamine / dichloromethane / 2 h / 50 °C

5: lithium hydroxide monohydrate; water / tetrahydrofuran / 4 h / 20 °C

With tetrachloromethane; lithium hydroxide monohydrate; diphenyl phosphoryl azide; water; tetra-(n-butyl)ammonium iodide; triethylamine; triphenylphosphine; In tetrahydrofuran; dichloromethane; toluene; 3: Curtius rearrangement;

DOI:10.1016/j.bmcl.2012.05.012

Reference yield:

methyl 5-(4-(chloromethyl)phenyl)-3-methylisoxazole-4-carboxylate (1384485-34-0) → (+/-)-Ki16425 (355025-24-0)

Guidance literature:

Multi-step reaction with 4 steps

1: lithium hydroxide monohydrate; water / tetrahydrofuran / 19 h / 20 °C

2: diphenyl phosphoryl azide; triethylamine / toluene / 0.5 h / 120 °C

3: tetra-(n-butyl)ammonium iodide; triethylamine / dichloromethane / 2 h / 50 °C

4: lithium hydroxide monohydrate; water / tetrahydrofuran / 4 h / 20 °C

With lithium hydroxide monohydrate; diphenyl phosphoryl azide; water; tetra-(n-butyl)ammonium iodide; triethylamine; In tetrahydrofuran; dichloromethane; toluene; 2: Curtius rearrangement;

DOI:10.1016/j.bmcl.2012.05.012

upstream raw materials:

methyl 3-(4-((tert-butyldimethylsilyloxy)methyl)phenyl)-prop-2-ynoate

methyl 5-(4-((tert-butyldimethylsilyloxy)methyl)phenyl)-3-methylisoxazole-4-carboxylate

methyl 5-(4-(hydroxymethyl)phenyl)-3-methylisoxazole-4-carboxylate

methyl 5-(4-(chloromethyl)phenyl)-3-methylisoxazole-4-carboxylate

Refernces

• 1、 -. "Novel isoxazole and thiazole compounds and use thereof as drugs". . . Retrieved 2008/06/13.