Basic information Safety Supplier Related

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

Basic information Safety Supplier Related

5-((7-(BENZYLOXY)QUINAZOLIN-4-YL)AMINO)-4-FLUORO-2-METHYLPHENOL Basic information

Product Name:
5-((7-(BENZYLOXY)QUINAZOLIN-4-YL)AMINO)-4-FLUORO-2-METHYLPHENOL
Synonyms:
  • 5-((7-(BENZYLOXY)QUINAZOLIN-4-YL)AMINO)-4-FLUORO-2-METHYLPHENOL
  • KDR/FLK-1 INHIBITOR V
  • VEGF RECEPTOR 2 KINASE INHIBITOR V
  • ZM323881
  • 4-Fluoro-2-methyl-5-[[7-(phenylmethoxy)-4-quinazolinyl]amino]phenol
  • CS-744
  • Phenol, 4-fluoro-2-methyl-5-[[7-(phenylmethoxy)-4-quinazolinyl]amino]-
CAS:
193001-14-8
MF:
C22H18FN3O2
MW:
375.4
Mol File:
Mol File
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5-((7-(BENZYLOXY)QUINAZOLIN-4-YL)AMINO)-4-FLUORO-2-METHYLPHENOL Chemical Properties

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)
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5-((7-(BENZYLOXY)QUINAZOLIN-4-YL)AMINO)-4-FLUORO-2-METHYLPHENOL Usage And Synthesis

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.

5-((7-(BENZYLOXY)QUINAZOLIN-4-YL)AMINO)-4-FLUORO-2-METHYLPHENOLSupplier

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5-((7-(BENZYLOXY)QUINAZOLIN-4-YL)AMINO)-4-FLUORO-2-METHYLPHENOL(193001-14-8)Related Product Information