4-(4-Fluorophenyl)-2-(4-hydroxyphenyl)-5-(4-pyridyl)-1H-imidazole

Base Information

• Chemical Name: 4-(4-Fluorophenyl)-2-(4-hydroxyphenyl)-5-(4-pyridyl)-1H-imidazole
• CAS No.: 152121-30-7
• Deprecated CAS: 194615-33-3
• Molecular Formula: C20H14FN3O
• Molecular Weight: 331.349
• Hs Code.: 29333990
• European Community (EC) Number: 633-977-2
• UNII: PVX798P8GI
• DSSTox Substance ID: DTXSID7041120
• Nikkaji Number: J638.383A
• Wikidata: Q27088696,Q27164687
• Pharos Ligand ID: H3ZMJGUNM2W9
• Metabolomics Workbench ID: 130008
• ChEMBL ID: CHEMBL278041
• Mol file: 152121-30-7.mol

Synonyms:4-(4-fluorophenyl)-2-(4-hydroxyphenyl)-5-(4-pyridyl)imidazole;phenol, 4-(4-(4-fluorophenyl)-5-(4-pyridinyl)-1h-imidazol-2-yl)-;SB 202190;SB-202190;SB202190

Chemical Property of 4-(4-Fluorophenyl)-2-(4-hydroxyphenyl)-5-(4-pyridyl)-1H-imidazole

Chemical Property:

• Appearance/Colour: pale yellow
• Vapor Pressure: 1.86E-10mmHg at 25°C
• Melting Point: 240-243℃
• Refractive Index: 1.66
• Boiling Point: 565.705 °C at 760 mmHg
• PKA: 9.14±0.15(Predicted)
• Flash Point: 295.928 °C
• PSA: 61.80000
• Density: 1.311 g/cm³
• LogP: 4.65040
• Storage Temp.: 2-8°C
• Solubility.: DMSO: 30?mg/mL, soluble
• XLogP3: 3.7
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 3
• Exact Mass: 331.11209024
• Heavy Atom Count: 25
• Complexity: 415

Purity/Quality:

99%, ^*data from raw suppliers

SB 202190 ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36/37

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: C1=CC(=CC=C1C2=NC(=C(N2)C3=CC=NC=C3)C4=CC=C(C=C4)F)O
• Description: SB 202190 is a selective, potent, cell-permeable inhibitor of p38 MAP kinases, inhibiting p38α (SAPK2A, MAPK14) and p38β (SAPK2B, MAPK11) with IC50 values of 50 and 100 nM, respectively. When tested at 10 μM, SB 202190 has negligible effects on a range of other kinases, including other MAP kinases (ERKs, JNKs). Pyridinyl imidazole inhibitors, including Phenol,4-[4-(4-fluorophenyl)-5-(4-pyridinyl)-1H-imidazol-2-yl]-, directly bind p38 MAP kinases in the ATP binding pocket. Recently, SB 202190 has been used to elucidate the roles of p38 MAP kinases in inflammatory cytokine expression, nicotine-induced receptor expression, and HIV-mediated depressive disorder.
• Uses: SB 202190 is a DFG inhibitor used in the treatment of colorectal cancer. It is a highly selective, potent inhibitor of p38 MAP kinase. SB-202190 is able to promote proliferation of C6 cells in lower c oncentration but induced apoptosis in higher levels. Studies show that SB202190 can protect neural function from ischemia/reperfusion injury and regulate the activation of Bcl-2 and Bax protein after ischemia/reperfusion in rat. SB 202190 is a DFG inhibitor used in the treatment of colorectal cancer. It is a highly selective, potent inhibitor of p38 MAP kinase. SB-202190 is able to promote proliferation of C6 cells in lower concentration but induced apoptosis in higher levels. Studies show that SB202190 can protect neural function from ischemia/reperfusion injury and regulate the activation of Bcl-2 and Bax protein after ischemia/reperfusion in rat.

Technology Process of 4-(4-Fluorophenyl)-2-(4-hydroxyphenyl)-5-(4-pyridyl)-1H-imidazole

There total 9 articles about 4-(4-Fluorophenyl)-2-(4-hydroxyphenyl)-5-(4-pyridyl)-1H-imidazole 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:

4-(4-Fluoro-phenyl)-2-(4-hydroxy-phenyl)-5-pyridin-4-yl-imidazol-1-ol (152121-31-8) → 4-(4-fluorophenyl)-2-(4-hydroxyphenyl)-5-(pyridin-4-yl)-1H-imidazole (152121-30-7)

Guidance literature:

With triethyl phosphite; In N,N-dimethyl-formamide; at 100 ℃; for 2h;

DOI:10.1016/S0968-0896(96)00212-X

Reference yield:

4-fluoro-N-methoxy-N-methylbenzamide (116332-54-8) → 4-(4-fluorophenyl)-2-(4-hydroxyphenyl)-5-(pyridin-4-yl)-1H-imidazole (152121-30-7)

Guidance literature:

Multi-step reaction with 2 steps

1.1: LDA / tetrahydrofuran / -30 °C

1.2: tetrahydrofuran / -30 - 0 °C

2.1: Cu(OAc)2; NH₄OAc; HOAc / 4 h / 115 °C

With copper diacetate; ammonium acetate; acetic acid; lithium diisopropyl amide; In tetrahydrofuran;

DOI:10.1016/S0960-894X(01)00498-X

Reference yield:

4-((tert-butyldimethylsilyloxy)methyl)pyridine (117423-41-3) → 4-(4-fluorophenyl)-2-(4-hydroxyphenyl)-5-(pyridin-4-yl)-1H-imidazole (152121-30-7)

Guidance literature:

Multi-step reaction with 2 steps

1.1: LDA / tetrahydrofuran / -30 °C

1.2: tetrahydrofuran / -30 - 0 °C

2.1: Cu(OAc)2; NH₄OAc; HOAc / 4 h / 115 °C

With copper diacetate; ammonium acetate; acetic acid; lithium diisopropyl amide; In tetrahydrofuran;

DOI:10.1016/S0960-894X(01)00498-X

upstream raw materials:

4-(4-Fluoro-phenyl)-2-(4-hydroxy-phenyl)-5-pyridin-4-yl-imidazol-1-ol

4-hydroxy-benzaldehyde

2-(tert-butyldimethyl-silyloxy)-1-(4-fluorophenyl)-2-pyridin-4-yl-ethanone

4-fluoro-N-methoxy-N-methylbenzamide

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