Tyrphostin B42

Base Information

• Chemical Name: Tyrphostin B42
• CAS No.: 133550-30-8
• Molecular Formula: C17H14N2O3
• Molecular Weight: 294.31
• Hs Code.: 29269090
• European Community (EC) Number: 664-282-2
• DSSTox Substance ID: DTXSID5040960
• Nikkaji Number: J1.541.147C,J412.923G
• Wikidata: Q27074341
• NCI Thesaurus Code: C1778
• Pharos Ligand ID: SUDMV8HNLTDZ
• ChEMBL ID: CHEMBL56543
• Mol file: 133550-30-8.mol

Synonyms:AG 490;AG-490;AG490;alpha-cyano-(3,4-dihydroxy)-N-benzylcinnamide;n-benzyl-3,4-dihydroxy-benzylidenecyanoacetamide;tyrphostin AG-490;tyrphostin B42

Chemical Property of Tyrphostin B42

Chemical Property:

• Appearance/Colour: Yellow solid
• Vapor Pressure: 9.95E-16mmHg at 25°C
• Melting Point: 215
• Refractive Index: 1.678
• Boiling Point: 615.21 °C at 760 mmHg
• PKA: 8.75±0.10(Predicted)
• Flash Point: 325.867 °C
• PSA: 93.35000
• Density: 1.337 g/cm³
• LogP: 2.71208
• Storage Temp.: −20°C
• Solubility.: ethanol: 5 mg/mL
• XLogP3: 2.4
• Hydrogen Bond Donor Count: 3
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 4
• Exact Mass: 294.10044231
• Heavy Atom Count: 22
• Complexity: 460

Purity/Quality:

99% ^*data from raw suppliers

TyrphostinB42 ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi,N,T
• Statements: 36/37/38-50-25
• Safety Statements: 26-36-61-45

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: C1=CC=C(C=C1)CNC(=O)C(=CC2=CC(=C(C=C2)O)O)C#N
• Isomeric SMILES: C1=CC=C(C=C1)CNC(=O)/C(=C/C2=CC(=C(C=C2)O)O)/C#N
• Description: AG-490 (133550-30-8) is a potent inhibitor of the JAK2 tyrosine kinase. In acute lymphoblastic leukemia (ALL) cells, which abundantly express JAK-2, AG-490 dose-dependently blocked cell growth, induced apoptosis and inhibited DNA synthesis. Blocks the growth of all pre-B ALL cells with no effect on normal B or T cells. Does not significantly inhibit other kinases such as Lck, Lyn, Btk, Syk and Src. Reduces liver injury in LPS-induced shock.3 AG-490 is a useful tool for exploring the role of JAK2/STAT3 pathway in physiologic processes.4
• Uses: AG 490 is a potent epidermal growth factor receptor kinase autophosphorylation inhibitor with an IC50 of 100 nM and 56.8 μM for EGFR and JAK, respectively. Tyrphostin AG has been used to block IL-6 cytokine signaling to study its effects on glial cell reactivity5. AG 490 has also been used as a JAK2 inhibitor in human umbilical vein endothelial cells6.

Technology Process of Tyrphostin B42

There total 4 articles about Tyrphostin B42 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: 79.0%

N-Benzylcyanoacetamide (10412-93-8) + 3,4-dihydroxybenzaldehyde (139-85-5) → tyrphostin B42 (133550-30-8,134036-52-5)

Guidance literature:

DOI:10.1021/jm00110a022

Reference yield:

benzylamine (100-46-9) → tyrphostin B42 (133550-30-8,134036-52-5)

Guidance literature:

Multi-step reaction with 2 steps

1: 67 percent / acetonitrile / 4 h / Heating

2: 36 percent / piperidine / 3 h / Heating

With piperidine; In acetonitrile; 1: Acylation / 2: Condensation;

DOI:10.1021/jm990199u

Reference yield:

benzylamine (100-46-9) → tyrphostin B42 (133550-30-8,134036-52-5)

Guidance literature:

Multi-step reaction with 2 steps

1: 38 percent / 16 h / 100 °C

2: 79 percent

DOI:10.1021/jm00110a022

upstream raw materials:

N-Benzylcyanoacetamide

3,4-dihydroxybenzaldehyde

benzylamine

Refernces

• 1、 -. "Antiangiogenic combination therapy for the treatment of cancer". . . Retrieved 2008/06/13.
• 2、 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.