1-(2-Methoxyphenyl)-3-(2-pyridin-3-ylquinazolin-4-yl)urea

Base Information

• Chemical Name: 1-(2-Methoxyphenyl)-3-(2-pyridin-3-ylquinazolin-4-yl)urea
• CAS No.: 280570-45-8
• Molecular Formula: C₂₁H₁₇N₅O₂
• Molecular Weight: 371.398
• DSSTox Substance ID: DTXSID00398737
• Nikkaji Number: J1.372.036C
• Wikidata: Q27089203
• Pharos Ligand ID: A71DAD7RN3X6
• ChEMBL ID: CHEMBL70880
• Mol file: 280570-45-8.mol

Synonyms:VUF 5574;280570-45-8;VUF5574;VUF-5574;1-(2-methoxyphenyl)-3-(2-pyridin-3-ylquinazolin-4-yl)urea;CHEMBL70880;3-(2-methoxyphenyl)-1-(2-pyridin-3-ylquinazolin-4-yl)urea;1-(2-Methoxyphenyl)-3-(2-(pyridin-3-yl)quinazolin-4-yl)urea;NCGC00016084-01;Lopac-V-5888;D01AAI;Lopac0_001247;SCHEMBL935642;GTPL3280;DTXSID00398737;YRAFEJSZTVWUMD-UHFFFAOYSA-N;BDBM50088475;AKOS000749577;CCG-205321;NCGC00016084-02;NCGC00016084-03;NCGC00016084-04;NCGC00016084-05;NCGC00094488-01;NCGC00094488-02;NCGC00094488-03;NCGC00094488-04;MS-25980;HY-103189;CS-0025280;EU-0101247;EC-000.2112;V 5888;SR-01000076193;J-016958;SR-01000076193-1;Q27089203;1-(2-Methoxy-phenyl)-3-(2-pyridin-3-yl-quinazolin-4-yl)-urea;N-(2-Methoxyphenyl)-N'-[2-(3-pyridinyl)-4-quinazolinyl]-urea;N-(2-Methoxyphenyl)-N'-[2-(3-pyrindinyl)-4-quinazolinyl]-urea

Chemical Property of 1-(2-Methoxyphenyl)-3-(2-pyridin-3-ylquinazolin-4-yl)urea

Chemical Property:

• Vapor Pressure: 4.14E-08mmHg at 25°C
• Melting Point: 257-258 °C
• Refractive Index: 1.725
• Boiling Point: 444.8 °C at 760 mmHg
• PKA: -2.06±0.43(Predicted)
• Flash Point: 222.8 °C
• PSA: 89.03000
• Density: 1.36 g/cm³
• LogP: 4.49040
• Storage Temp.: Store at RT
• Solubility.: DMSO: 1.5 mg/mL, soluble
• XLogP3: 3
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 4
• Exact Mass: 371.13822480
• Heavy Atom Count: 28
• Complexity: 519

Purity/Quality:

99% ^*data from raw suppliers

VUF 5574 ^*data from reagent suppliers

Safty Information:

• Safety Statements: 22-24/25

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: COC1=CC=CC=C1NC(=O)NC2=NC(=NC3=CC=CC=C32)C4=CN=CC=C4
• 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.

Technology Process of 1-(2-Methoxyphenyl)-3-(2-pyridin-3-ylquinazolin-4-yl)urea

There total 4 articles about 1-(2-Methoxyphenyl)-3-(2-pyridin-3-ylquinazolin-4-yl)urea which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 77.0%

1-Isocyanato-2-methoxy-benzene (700-87-8) + 4-amino-2-(pyridin-3-yl)quinazoline (273408-90-5) → VUF 5574 (280570-45-8)

Guidance literature:

In acetonitrile; at 30 - 50 ℃;

DOI:10.1021/jm000002u

Reference yield:

pyridine-3-carbonitrile (100-54-9,121697-66-3,1232169-17-3,68271-95-4) → VUF 5574 (280570-45-8)

Guidance literature:

Multi-step reaction with 2 steps

1.1: sodium hydride / tetrahydrofuran / 0 °C

1.2: 86 percent / tetrahydrofuran / 20 h / Heating

2.1: 77 percent / acetonitrile / 30 - 50 °C

With sodium hydride; In tetrahydrofuran; acetonitrile; 1.1: Deprotonation / 1.2: Cycloaddition / 2.1: Addition;

DOI:10.1021/jm000002u

Reference yield:

anthranilic acid nitrile (1885-29-6) → VUF 5574 (280570-45-8)

Guidance literature:

Multi-step reaction with 2 steps

1.1: sodium hydride / tetrahydrofuran / 0 °C

1.2: 86 percent / tetrahydrofuran / 20 h / Heating

2.1: 77 percent / acetonitrile / 30 - 50 °C

With sodium hydride; In tetrahydrofuran; acetonitrile; 1.1: Deprotonation / 1.2: Cycloaddition / 2.1: Addition;

DOI:10.1021/jm000002u

upstream raw materials:

1-Isocyanato-2-methoxy-benzene

4-amino-2-(pyridin-3-yl)quinazoline

pyridine-3-carbonitrile

anthranilic acid nitrile

Refernces

• 1、 Van Muijlwijk-Koezen, Jacqueline E.,Timmerman, Henk,Van Der Goot, Henk,Menge, Wiro M. P. B.,Von Drabbe Künzel, Jacobien Frijtag,De Groote, Miriam,Ijzerman, Adriaan P.. "Isoquinoline and quinazoline urea analogues as antagonists for the human-adenosine A3 receptor". . p. 2227 - 2238. Retrieved 2007/10/03.