133550-35-3

133550-35-3 structure

Name: AG-494
Chemical Name: 2-cyano-3-(3,4-dihydroxyphenyl)-N-phenylprop-2-enamide
CAS Number: 133550-35-3
Molecular Formula: C₁₆H₁₂N₂O₃
Molecular Weight: 280.278
Catalog: Signaling Pathways Cell Cycle/DNA Damage CDK
Create Date: 2017-05-21 10:36:56
Modify Date: 2024-01-06 22:52:54
AG-494 (Tyrphostin AG 494) is a potent and selective EGFR tyrosine kinase inhibitor (IC50=0.7 μM). AG-494 inhibits the autophosphorylation of EGFR, ErbB2, HER1-2 and PDGF-R with IC50s 1.1, 39, 45 and 6 μM, respectively. AG-494 blocks Cdk2 activation and inhibits EGF-dependent DNA synthesis[1][2][3].

Name	2-cyano-3-(3,4-dihydroxyphenyl)-N-phenylprop-2-enamide
Synonyms	Tyrphostin 48 2-Propenamide, 2-cyano-3-(3,4-dihydroxyphenyl)-N-phenyl-, (2E)- HMS3266B19 (2E)-2-Cyano-3-(3,4-dihydroxyphenyl)-N-phenylacrylamide AG-494

Description	AG-494 (Tyrphostin AG 494) is a potent and selective EGFR tyrosine kinase inhibitor (IC50=0.7 μM). AG-494 inhibits the autophosphorylation of EGFR, ErbB2, HER1-2 and PDGF-R with IC50s 1.1, 39, 45 and 6 μM, respectively. AG-494 blocks Cdk2 activation and inhibits EGF-dependent DNA synthesis[1][2][3].
Related Catalog	Research Areas >> Cancer Signaling Pathways >> JAK/STAT Signaling >> EGFR Signaling Pathways >> Protein Tyrosine Kinase/RTK >> EGFR Signaling Pathways >> Cell Cycle/DNA Damage >> CDK
Target	EGFR:0.7 μM (IC50)
In Vitro	In DHER-14 cells, AG 494 inhibits Cdk2 activation and EGF-dependent DNA synthesis[2]. AG-494 significantly prevents NF-kB activation in silica-stimulated cells, and also reduces NF-kB activation in H2O2-treated cells[4]. AG-494 (3-9 μM; 5-7 days) inhibits BMP9-induced ALP activity in a dose-dependent manner[5].
References	[1]. Gazit A, et al. Tyrphostins. 2. Heterocyclic and alpha-substituted benzylidenemalononitrile tyrphostins as potent inhibitors of EGF receptor and ErbB2/neu tyrosine kinases. J Med Chem. 1991;34(6):1896-1907. [2]. Osherov N, et al. Tyrphostin AG 494 blocks Cdk2 activation. FEBS Lett. 1997;410(2-3):187-190. [3]. Osherov N, et al. Selective inhibition of the epidermal growth factor and HER2/neu receptors by tyrphostins. J Biol Chem. 1993 May 25;268(15):11134-42. [4]. Liu X, Qin J, et al. Cross-talk between EGF and BMP9 signalling pathways regulates the osteogenic differentiation of mesenchymal stem cells. J Cell Mol Med. 2013;17(9):1160-1172. [5]. Jihee Lee Kang, et al. SILICA-INDUCED NUCLEAR FACTOR- k B ACTIVATION: INVOLVEMENT OF REACTIVE OXYGEN SPECIES AND PROTEIN TYROSINE KINASE ACTIVATION. Journal of Toxicology and Environmental Health, Part A.

Density	1.4±0.1 g/cm3
Boiling Point	586.9±50.0 °C at 760 mmHg
Melting Point	249 °C(dec.)
Molecular Formula	C₁₆H₁₂N₂O₃
Molecular Weight	280.278
Flash Point	308.8±30.1 °C
Exact Mass	280.084778
PSA	93.35000
LogP	2.40
Vapour Pressure	0.0±1.7 mmHg at 25°C
Index of Refraction	1.736

Hazard Codes	C
Safety Phrases	22-24/25

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