| Identification | Back Directory | [Name]
VUF 5574 | [CAS]
280570-45-8 | [Synonyms]
VUF 5574
N-(2-METHOXYPHENYL)-N-[2-(3-PYRIDINYL)-4-QUINAZOLINYL]-UREA
1-(2-Methoxy-phenyl)-3-(2-pyridin-3-yl-quinazolin-4-yl)-urea
N-(2-METHOXYPHENYL)-N'-[2-(3-PYRINDINYL)-4-QUINAZOLINYL]-UREA
Urea, N-(2-methoxyphenyl)-N'-[2-(3-pyridinyl)-4-quinazolinyl]- | [Molecular Formula]
C21H17N5O2 | [MDL Number]
MFCD06691423 | [MOL File]
280570-45-8.mol | [Molecular Weight]
371.39 |
| Chemical Properties | Back Directory | [Melting point ]
257-258 °C | [Boiling point ]
444.8±45.0 °C(Predicted) | [density ]
1.360±0.06 g/cm3(Predicted) | [storage temp. ]
Store at RT | [solubility ]
DMSO: 1.5 mg/mL, soluble | [form ]
solid | [pka]
-2.06±0.43(Predicted) | [color ]
white | [InChI]
1S/C21H17N5O2/c1-28-18-11-5-4-10-17(18)24-21(27)26-20-15-8-2-3-9-16(15)23-19(25-20)14-7-6-12-22-13-14/h2-13H,1H3,(H2,23,24,25,26,27) | [InChIKey]
YRAFEJSZTVWUMD-UHFFFAOYSA-N | [SMILES]
COc1ccccc1NC(=O)Nc2nc(nc3ccccc23)-c4cccnc4 |
| Hazard Information | Back Directory | [Description]
VUF 5574 is an antagonist of the adenosine A3 receptor (Ki = 4.03 nM for the recombinant human receptor). It is greater than 2,500-fold selective for adenosine A3 over A1 and A2A receptors. VUF 5574 (100 nM) decreases phosphorylation of ERK1/2 induced by adenosine in isolated porcine coronary artery smooth muscle cells. It increases oxygen-glucose deprivation-induced reductions in the amplitude of field excitatory postsynaptic potentials (EPSPs) in a rat hippocampal slice model of ischemia when used at a concentration of 100 nM. VUF 5574 (2 μg, intracisternal) reduces sodium nitroprusside-induced heart rate increases in rats. | [Uses]
VUF 5574 is an adenosine A3 receptor antagonist. | [Biological Activity]
Potent, selective, competitive antagonist for the human adenosine A 3 receptor (K i = 4 nM). Displays ≥ 2500-fold selectivity over A 1 and A 2A receptors. | [IC 50]
Recombinant Human Adenosine A3 receptor (A3R): 4.03 nM (Ki) | [References]
[1] JACQUELINE E. VAN MUIJLWIJK-KOEZEN. Isoquinoline and Quinazoline Urea Analogues as Antagonists for the Human Adenosine A3 Receptor[J]. Journal of Medicinal Chemistry, 2000, 43 11: 2227-2238. DOI: 10.1021/jm000002u
[2] JIANZHONG SHEN. Cell-signaling evidence for adenosine stimulation of coronary smooth muscle proliferation via the A1 adenosine receptor.[J]. Circulation research, 2005, 97 6: 574-582. DOI: 10.1161/01.res.0000181159.83588.4b
[3] ANNA MARIA PUGLIESE. A3 adenosine receptor antagonists delay irreversible synaptic failure caused by oxygen and glucose deprivation in the rat CA1 hippocampus in vitro[J]. British Journal of Pharmacology, 2009, 147 5: 524-532. DOI: 10.1038/sj.bjp.0706646
[4] MAHMOUD M. EL-MAS. Role of adenosine A2A receptor signaling in the nicotine-evoked attenuation of reflex cardiac sympathetic control[J]. Toxicology and applied pharmacology, 2011, 254 3: Pages 229-237. DOI: 10.1016/j.taap.2011.04.014 |
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