Kartogenin

Base Information

• Chemical Name: Kartogenin
• CAS No.: 4727-31-5
• Molecular Formula: C20H15NO3
• Molecular Weight: 317.344
• Hs Code.: 2924299090
• European Community (EC) Number: 803-978-4
• UNII: Q93BBN11CP
• DSSTox Substance ID: DTXSID30385074
• Nikkaji Number: J3.342.662C
• Wikidata: Q27287128
• Metabolomics Workbench ID: 144472
• ChEMBL ID: CHEMBL3185782
• Mol file: 4727-31-5.mol

Synonyms:2-(4-biphenylylcarbamoyl)benzoic acid;kartogenin

Chemical Property of Kartogenin

Chemical Property:

• Melting Point: 272 °C
• Boiling Point: 464.4±38.0 °C(Predicted)
• PKA: 3.45±0.36(Predicted)
• PSA: 66.40000
• Density: 1.289±0.06 g/cm3(Predicted)
• LogP: 4.37710
• Storage Temp.: room temp
• Solubility.: DMSO: >15mg/mL
• XLogP3: 4.2
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 4
• Exact Mass: 317.10519334
• Heavy Atom Count: 24
• Complexity: 436

Purity/Quality:

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

Kartogenin ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xn,N
• Hazard Codes: Xn,N
• Statements: 22-36-50/53
• Safety Statements: 60-61

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1=CC=C(C=C1)C2=CC=C(C=C2)NC(=O)C3=CC=CC=C3C(=O)O
• Description: Kartogenin potently induces differentiation of human mesenchymal stem cells into chondrocytes with an EC50 value of 100 nM. Kartogenin induces chondrogenesis by binding the actin-binding protein, filamin A, which disrupts its interaction with the transcription factor core-binding factor β subunit (CBFβ). When dissociated from filamin A, CBFβ translocates to the nucleus and forms a transcriptional complex with the runt-related transcription factor RUNX1, which enables chondrocyte differentiation. Kartogenin has been shown to promote cartilage repair in a mouse model of osteoarthritis and to protect against cytokine-induced damage in osteoarthritic bovine articular chondrocytes in vitro.
• Uses: Kartogenin is a potent, selective, and non-cytotoxic downstream RUNX1 and RUNX2 modulator. Kartogenin causes mesenchymal stem cells found in joints to differentiate into chondrocyte cells that can build cartilage where it has been destroyed.

Technology Process of Kartogenin

There total 1 articles about Kartogenin 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:

→ kartogenin (4727-31-5)

Guidance literature:

Reference yield:

kartogenin (4727-31-5) + ethylamine (75-04-7,85404-22-4) → C22H20N2O2

Guidance literature:

kartogenin; ethylamine; With N-ethyl-N,N-diisopropylamine; In N,N-dimethyl-formamide; for 0.5h;

With benzotriazol-1-yloxyl-tris-(pyrrolidino)-phosphonium hexafluorophosphate; In N,N-dimethyl-formamide; at 20 ℃; for 6h;

Reference yield:

methanol (67-56-1) + kartogenin (4727-31-5) → methyl 2-([1,1’-biphenyl]-4-ylcarbamoyl)benzoate

Guidance literature:

With dmap; dicyclohexyl-carbodiimide; In dichloromethane; dimethyl sulfoxide; at 0 - 20 ℃; for 12.5h;

Refernces

• 1、 -. "NOVEL IMMUNOMODULATOR AND ANTI-INFLAMMATORY COMPOUNDS". Page/Page column 37. . Retrieved 2011/11/13.
• 2、 -. "Therapeutic and diagnostic ligand systems comprising transport molecule binding properties and medicaments containing the same". . . Retrieved 2008/06/13.