(E)-2-cyano-3-(4-hydroxy-3,5-diisopropylphenyl)-N-(3-phenylpropyl)acrylamide

Product Name(E)-2-cyano-3-(4-hydroxy-3,5-diisopropylphenyl)-N-(3-phenylpropyl)acrylamide
CAS168835-82-3
MFC25H30N2O2
MW390.52
EINECS
MOL File168835-82-3.mol

Chemical Properties

Melting point	126 °C
Boiling point	590.6±50.0 °C(Predicted)
Density	1.100±0.06 g/cm3(Predicted)
storage temp.	-20°C
solubility	Soluble in DMSO.
pka	10.30±0.36(Predicted)
form	powder
color	white to beige
Stability	Stable for 1 year from date of purchase as supplied. Solutions in DMSO may be stored at -20° for up to 3 months.
InChI	1S/C25H30N2O2/c1-17(2)22-14-20(15-23(18(3)4)24(22)28)13-21(16-26)25(29)27-12-8-11-19-9-6-5-7-10-19/h5-7,9-10,13-15,17-18,28H,8,11-12H2,1-4H3,(H,27,29)/b21-13+
InChIKey	JANPYFTYAGTSIN-FYJGNVAPSA-N
SMILES	N(CCCc2ccccc2)C(=O)\C(=C\c1cc(c(c(c1)C(C)C)O)C(C)C)\C#N
CAS DataBase Reference	168835-82-3

Safety Information

WGK Germany	WGK 3
HS Code	2926.90.4801
Storage Class	11 - Combustible Solids
Hazard Classifications	Eye Irrit. 2 Skin Irrit. 2 STOT SE 3

Usage And Synthesis

Description

SU-1498 (168835-82-3) is a potent, reversible, selective inhibitor of VEGFR-2, also known as Flk-1 (IC50 = 700 nM). Inhibition of VEGFR-2 blocks angiogenesis in both in vitro and in vivo models. Cell permeable.

Uses

SU 1498 is an inhibitor of VEGF receptor kinase.

Definition

ChEBI: SU1498 is a monocarboxylic acid amide obtained by formal condensation of the carboxy group of (2E)-2-cyano-3-[4-hydroxy-3,5-di(propan-2-yl)phenyl]prop-2-enoic acid with the amino group of 3-phenylpropylamine. It has a role as a vascular endothelial growth factor receptor antagonist. It is an enamide, a member of phenols, a nitrile, a monocarboxylic acid amide and a secondary carboxamide.

Biochem/physiol Actions

SU1498 is a potent and selective inhibitor of the VEGFR2 receptor kinase, Flk-1 with an IC50 value of 700 nM. SU1498 is a very weak inhibitor of PDGFR-kinase, EGFR-kinase and HER-2 kinase with IC50 values > 50 μM. SU1498 has been used to study the role of VEGFR2 (Flk-1) in a variety of biological activities including angiogenesis, tumor growth inhibition, and stem cell proliferation.

IC 50

Flk-1: 700 nM (IC₅₀)

References

[1] SU JIN CHO. Retinoic acid and erythropoietin maintain alveolar development in mice treated with an angiogenesis inhibitor.[J]. American Journal of Respiratory Cell and Molecular Biology, 2005, 33 6: 622-628. DOI:10.1165/rcmb.2005-0050oc
[2] YINGXIAO WANG. Interplay between integrins and FLK-1 in shear stress-induced signaling.[J]. American journal of physiology. Cell physiology, 2002, 283 5: C1540-7. DOI:10.1152/ajpcell.00222.2002
[3] L M STRAWN. Flk-1 as a target for tumor growth inhibition.[J]. Cancer research, 1996, 56 15: 3540-3545.

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