Linifanib

Base Information

• Chemical Name: Linifanib
• CAS No.: 796967-16-3
• Molecular Formula: C21H18FN5O
• Molecular Weight: 375.405
• Hs Code.: 2933998090
• European Community (EC) Number: 681-638-2
• UNII: CO93X137CW
• ChEMBL ID: CHEMBL223360
• DSSTox Substance ID: DTXSID40229834
• NCI Thesaurus Code: C71759
• Nikkaji Number: J2.388.171C
• Pharos Ligand ID: JUWYAYT6Q9TY
• Wikidata: Q6554172
• Wikipedia: Linifanib
• Mol file: 796967-16-3.mol

Synonyms:1-(4-(3-amino-1H-indazol-4-yl)phenyl)-3-(2-fluoro-5-methylphenyl)urea;A 741439;A-741439;A741439;ABT 869;ABT-869;ABT869;linifanib;N-(4-(3-amino-1H-indazol-4-yl)phenyl)-N1-(2-fluoro-5-methylphenyl)urea;RG 3635;RG-3635;RG3635

Chemical Property of Linifanib

Chemical Property:

• Appearance/Colour: Solid
• Vapor Pressure: 0mmHg at 25°C
• Melting Point: 180-183 °C (dec.)
• Refractive Index: 1.766
• Boiling Point: 542.203 °C at 760 mmHg
• PKA: 13.30±0.70(Predicted)
• Flash Point: 281.715 °C
• PSA: 95.83000
• Density: 1.424 g/cm³
• LogP: 5.63080
• Storage Temp.: -20?C Freezer
• Solubility.: DMSO, Methanol
• XLogP3: 3.9
• Hydrogen Bond Donor Count: 4
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 3
• Exact Mass: 375.14953838
• Heavy Atom Count: 28
• Complexity: 541

Purity/Quality:

Linifanib ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC1=CC(=C(C=C1)F)NC(=O)NC2=CC=C(C=C2)C3=C4C(=CC=C3)NN=C4N
• Recent ClinicalTrials: Safety, Tolerability and Efficacy of Vaginal Suppositories for Treatment of the Endometriosis
• Recent EU Clinical Trials: A Dose-Escalation Study of AL-39324 Suspension versus Lucentis? for the Treatment
• Uses: Linifanib (ABT-869) is a novel, potent ATP-competitive RTK inhibitor for KDR, CSF-1R, Flt-1, Flt-3 and PDGFRβ with IC50 of 4 nM, 3 nM, 3 nM, 3 nM, and 66 nM respectively. Linifanib (ABT 869) is an oral tyrosine kinase inhibitor with antineoplasic activity. As a dual inhibitor, Linifanib, is being tested on several different cancers. An oral tyrosine kinase inhibitor with antineoplasic activity.

Technology Process of Linifanib

There total 10 articles about Linifanib 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: 84.0%

N-(2-fluoro-5-methylphenyl)-N'-[4-(4,4,5,5-tetramethyl-[1,3,2]-dioxaborolan-2-yl)phenyl]urea (796967-18-5) + 3-amino-4-chloro-1H-indazole (20925-60-4) → linifanib (796967-16-3)

Guidance literature:

With potassium phosphate; 1,1'-bis(di-tertbutylphosphino)ferrocene; palladium diacetate; In ethanol; water; at 55 ℃; for 1.5h; Inert atmosphere;

DOI:10.1021/op900208y

Reference yield: 74.8%

4-iodine-1H-indazol-3-ylamine (599191-73-8) + N-(2-fluoro-5-methylphenyl)-N'-[4-(4,4,5,5-tetramethyl-[1,3,2]-dioxaborolan-2-yl)phenyl]urea (796967-18-5) → linifanib (796967-16-3)

Guidance literature:

With dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH₂Cl₂; sodium carbonate; In ethanol; for 8h; Reflux;

Reference yield:

3-amino-4-fluorotoluene (452-84-6) → linifanib (796967-16-3)

Guidance literature:

Multi-step reaction with 2 steps

1: CH₂Cl₂ / 0 - 20 °C

2: Na₂CO₃ / Pd(dppf)Cl₂*CH₂Cl₂ / 1,2-dimethoxy-ethane; H₂O / 16 h / 85 °C

With sodium carbonate; dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH₂Cl₂; In 1,2-dimethoxyethane; dichloromethane; water; 2: Suzuki coupling;

DOI:10.1021/jm061280h

upstream raw materials:

4-iodine-1H-indazol-3-ylamine

N-(2-fluoro-5-methylphenyl)-N'-[4-(4,4,5,5-tetramethyl-[1,3,2]-dioxaborolan-2-yl)phenyl]urea

3-amino-4-fluorotoluene

2-fluoro-6-iodobenzonitrile

Refernces

• 1、 Marlow, Maria,Al-Ameedee, Mohammed,Smith, Thomas,Wheeler, Simon,Stocks, Michael J.. "Linifanib-a multi-targeted receptor tyrosine kinase inhibitor and a low molecular weight gelator". . p. 6384 - 6387. Retrieved 2015/04/14.
• 2、 -. "CRYSTALLINE CHEMOTHERAPEUTIC". Page/Page column 13. . Retrieved 2009/05/28.