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ChemicalBook--->CAS DataBase List--->193001-14-8

193001-14-8

193001-14-8 Structure

193001-14-8 Structure
IdentificationBack Directory
[Name]

5-((7-(BENZYLOXY)QUINAZOLIN-4-YL)AMINO)-4-FLUORO-2-METHYLPHENOL
[CAS]

193001-14-8
[Synonyms]

CS-744
ZM323881
KDR/FLK-1 INHIBITOR V
VEGF RECEPTOR 2 KINASE INHIBITOR V
5-((7-(BENZYLOXY)QUINAZOLIN-4-YL)AMINO)-4-FLUORO-2-METHYLPHENOL
4-Fluoro-2-methyl-5-[[7-(phenylmethoxy)-4-quinazolinyl]amino]phenol
Phenol, 4-fluoro-2-methyl-5-[[7-(phenylmethoxy)-4-quinazolinyl]amino]-
[Molecular Formula]

C22H18FN3O2
[MDL Number]

MFCD09037564
[MOL File]

193001-14-8.mol
[Molecular Weight]

375.4
Chemical PropertiesBack Directory
[Boiling point ]

543.6±50.0 °C(Predicted)
[density ]

1.342±0.06 g/cm3(Predicted)
[storage temp. ]

Store at -20°C
[solubility ]

Soluble in DMSO
[form ]

White to off-white solid.
[pka]

9.99±0.23(Predicted)
Hazard InformationBack Directory
[Definition]

ChEBI: ZM 323881 is a member of the class of quinazolines carrying 2-fluoro-4-methyl-5-hydroxyanilino and benzyloxy substituents at positions 4 and 7 respectively. It has a role as a vascular endothelial growth factor receptor antagonist. It is a benzyl ether, an aromatic ether, a member of quinazolines, a secondary amino compound, a substituted aniline, a halophenol, a member of monofluorobenzenes, an organic cation and a fluorophenol. It is a conjugate base of a ZM 323881(1+).
[Biological Activity]

zm323881 inhibits vegf-a-induced endothelial cell proliferation (ic50 = 8 nm) and vegf-r2 tyrosine phosphorylation (ic50 < 2 nm).vascular endothelial growth factor (vegf) increases vascular permeability and angiogenesis in many pathological conditions, such as cancer, arthritis, and diabetes. vegf activates vegf-receptor 1 (vegf-r1) and vegf-receptor 2 (vegf-r2) that autophosphorylate to initiate a signaling cascade resulting in angiogenesis and increased microvascular permeability. zm323881 is a potent and selective inhibitor of vegf-r2 tyrosine kinase.
[in vitro]

zm323881 was found to inhibit vegf-a-induced endothelial cell proliferation (ic50 = 8 nm) and vegf-r2 tyrosine phosphorylation in vitro (ic50 < 2 nm) [1].
[in vivo]

vegf-amediated increases in vascular permeability in perfused mesenteric microvessels in vivo were reversibly abolished by both zm323881 and the class iii receptor tyrosine kinase inhibitor ptk787/zk222584, suggesting that vegf-r2 phosphorylation is necessary for vegf-a-mediated increases in microvascular permeability in vivo [1].
[target]

VEGFR-2/KDR
[References]

[1] whittles ce, pocock tm, wedge sr, kendrew j, hennequin lf, harper sj, bates do. zm323881, a novel inhibitor of vascular endothelial growth factor-receptor-2 tyrosine kinase activity. microcirculation. 2002;9(6):513-22.
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