Tyrphostin B48

Base Information

• Chemical Name: Tyrphostin B48
• CAS No.: 139087-53-9
• Molecular Formula: C₁₆H₁₂N₂O₃
• Molecular Weight: 280.283
• European Community (EC) Number: 810-936-9
• DSSTox Substance ID: DTXSID201018515
• Nikkaji Number: J412.915F,J623.663D
• Wikidata: Q76304050
• NCI Thesaurus Code: C1785
• Pharos Ligand ID: S8TGXXVVGSPJ
• ChEMBL ID: CHEMBL56731
• Mol file: 139087-53-9.mol

Synonyms:(E)-isomer of AG 494;AG 494;AG-494;alpha-cyano-(3,4-dihydroxy)-N-phenylcinnamide;tyrphostin AG-494;tyrphostin B48

Chemical Property of Tyrphostin B48

Chemical Property:

• Boiling Point: 586.9°Cat760mmHg
• Flash Point: 308.8°C
• PSA: 84.56000
• Density: 1.416g/cm³
• LogP: 2.62528
• Storage Temp.: −20°C
• Solubility.: DMSO: soluble
• XLogP3: 2.7
• Hydrogen Bond Donor Count: 3
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 3
• Exact Mass: 280.08479225
• Heavy Atom Count: 21
• Complexity: 446

Purity/Quality:

98%min ^*data from raw suppliers

AG 494 ^*data from reagent suppliers

Safty Information:

• Safety Statements: 22-24/25

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1=CC=C(C=C1)NC(=O)C(=CC2=CC(=C(C=C2)O)O)C#N
• Isomeric SMILES: C1=CC=C(C=C1)NC(=O)/C(=C/C2=CC(=C(C=C2)O)O)/C#N
• Uses: AG 494 is a potent inhibitor of epidermal growth factor receptor (EGF-R). AG 494 has been found to inhibit cell growth even past the restriction point when receptor activation is no longer necessary; in particular AG 494 causes cells to arrest at late G1 and and during S phase.

Technology Process of Tyrphostin B48

There total 2 articles about Tyrphostin B48 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: 69.0%

cyanoacetanilide (621-03-4) + 3,4-dihydroxybenzaldehyde (139-85-5) → α-cyano-(3,4-dihydroxy)-N-phenylcinnamide (133550-35-3,139087-53-9)

Guidance literature:

DOI:10.1021/jm00110a022

Reference yield:

aniline (62-53-3) → α-cyano-(3,4-dihydroxy)-N-phenylcinnamide (133550-35-3,139087-53-9)

Guidance literature:

Multi-step reaction with 2 steps

1: 17 percent / 16 h / 100 °C

2: 69 percent

DOI:10.1021/jm00110a022

upstream raw materials:

cyanoacetanilide

3,4-dihydroxybenzaldehyde

aniline

Refernces

• 1、 Gazit, Aviv,Osherov, Nir,Posner, Israel,Yaish, Pnina,Poradosu, Enrique,et al.. "Tyrphostins. 2. Heterocyclic and α-Substituted Benzylidenemalonitrile Tyrphostins as Potent Inhibitors of EGF Receptor and ErbB2/neu Tyrosine Kinases". . p. 1896 - 1907. Retrieved 2007/10/02.