152121-30-7

Basic information

• Product Name: Phenol,4-[4-(4-fluorophenyl)-5-(4-pyridinyl)-1H-imidazol-2-yl]-
• Synonyms: C₂₀H₁₄FN₃O;4-(4-Fluorophenyl)-2-(4-hydroxyphenyl)-5-(4-pyridyl)-1H-imidazole
• CAS NO: 152121-30-7
• Molecular Formula: C₂₀H₁₄FN₃O
• Molecular Weight: 331.3431
• Product Categories: Inhibitors;inhibitor
• Mol File: 152121-30-7.mol
• Article Data: 7

Chemical Properties

• Melting Point: 240-243℃
• Boiling Point: 565.705 °C at 760 mmHg
• Flash Point: 295.928 °C
• Appearance: pale yellow
• Density: 1.311 g/cm³
• Vapor Pressure: 1.86E-10mmHg at 25°C
• Refractive Index: 1.66
• Storage Temp.: 2-8°C
• Solubility: DMSO: 30?mg/mL, soluble
• PKA: 9.14±0.15(Predicted)
• Stability: Stable for 2 years from date of purchase as supplied. Solutions in DMSO may be stored at -20° for up to 2 months.
• CAS DataBase Reference: Phenol,4-[4-(4-fluorophenyl)-5-(4-pyridinyl)-1H-imidazol-2-yl]-(CAS DataBase Reference)
• NIST Chemistry Reference: Phenol,4-[4-(4-fluorophenyl)-5-(4-pyridinyl)-1H-imidazol-2-yl]-(152121-30-7)
• EPA Substance Registry System: Phenol,4-[4-(4-fluorophenyl)-5-(4-pyridinyl)-1H-imidazol-2-yl]-(152121-30-7)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36/37
• WGK Germany: 3
• RTECS: SL4584000
• Hazardous Substances Data: 152121-30-7(Hazardous Substances Data)

Usage

Description

Phenol,4-[4-(4-fluorophenyl)-5-(4-pyridinyl)-1H-imidazol-2-yl]-, also known as SB 202190, is a potent, reversible, competitive, and cell-permeable inhibitor of p38 MAP kinase. It is a member of the class of imidazoles with specific substitutions at positions 2, 4, and 5, making it a selective inhibitor for p38 MAP kinases. SB 202190 has been used to study the roles of p38 MAP kinases in various biological processes and has shown potential in treating certain conditions.

Uses

Used in Pharmaceutical Industry:
Phenol,4-[4-(4-fluorophenyl)-5-(4-pyridinyl)-1H-imidazol-2-yl]is used as a DFG inhibitor for the treatment of colorectal cancer. It acts as a highly selective and potent inhibitor of p38 MAP kinase, promoting cell proliferation at lower concentrations and inducing apoptosis at higher levels.
Used in Neuroprotection:
In the field of neuroscience, Phenol,4-[4-(4-fluorophenyl)-5-(4-pyridinyl)-1H-imidazol-2-yl]is used to protect neural function from ischemia/reperfusion injury. It has been shown to regulate the activation of Bcl-2 and Bax proteins after ischemia/reperfusion in rats, potentially offering neuroprotective benefits.
Used in Inflammatory Research:
Phenol,4-[4-(4-fluorophenyl)-5-(4-pyridinyl)-1H-imidazol-2-yl]is utilized as a research tool to elucidate the roles of p38 MAP kinases in inflammatory cytokine expression. Its ability to inhibit p38 MAP kinases allows researchers to study the effects of these kinases on the immune response and inflammation.
Used in HIV-Mediated Depressive Disorder Research:
In the field of psychiatric research, Phenol,4-[4-(4-fluorophenyl)-5-(4-pyridinyl)-1H-imidazol-2-yl]is used to investigate the involvement of p38 MAP kinases in HIV-mediated depressive disorders. By inhibiting these kinases, researchers can gain insights into the molecular mechanisms underlying the development of depressive symptoms in HIV patients.
Used in Cellular Signaling Studies:
Phenol,4-[4-(4-fluorophenyl)-5-(4-pyridinyl)-1H-imidazol-2-yl]is employed as a research tool to study the roles of p38 MAP kinases in cellular signaling pathways, such as nicotine-induced receptor expression. This helps researchers understand the molecular basis of various cellular processes and the potential therapeutic applications of targeting these pathways.

Biological Activity

A highly selective, potent and cell-permeable inhibitor of p38 MAP kinase. Binds within the ATP pocket of the active kinase (K d = 38 nM, as measured in recombinant human p38), and selectively inhibits the p38 α and β isoforms (IC 50 = 50 and 100 nM at SAPK2a/p38 and SAPK2b/p38 β 2 respectively). Also available as part of the MAPK Inhibitor Tocriset? .

Biochem/physiol Actions

Cell permeable: yes

References

1) Young et al. (1997), Pyridinyl imidazole inhibitors of p38 mitogen-activated protein kinase bind in the ATP site; J. Biol. Chem., 272 12116 2) Davies et al. (2000), Specificity and mechanism of action of some commonly used protein kinase inhibitors; Biochem. J., 351 95 3) Manthey et al. (1998), SB202190, a selective inhibitor of p38 mitogen-activated protein kinase, is a powerful regulator of LPS-induced mRBAs in monocytes; J. Leukoc. Biol., 64 409 4) Nemoto et al. (1998), Induction of apoptosis by SB202190 through inhibition of p38β mitogen-activated protein kinase; J. Biol. Chem., 273 16415

InChI:InChI=1/C20H14FN3O/c21-16-5-1-13(2-6-16)18-19(14-9-11-22-12-10-14)24-20(23-18)15-3-7-17(25)8-4-15/h1-12,23-24H

Upstream product

• 152121-31-8 4-(4-Fluoro-phenyl)-2-(4-hydroxy-phenyl)-5-pyridin-4-yl-imidazol-1-ol 
• 123-08-0 4-hydroxy-benzaldehyde 
• 152122-41-3 2-(tert-butyldimethyl-silyloxy)-1-(4-fluorophenyl)-2-pyridin-4-yl-ethanone 
• 116332-54-8 4-fluoro-N-methoxy-N-methylbenzamide 
• 117423-41-3 4-((tert-butyldimethylsilyloxy)methyl)pyridine 
• 108-89-4 picoline 
• 6576-05-2 1-(4-fluorophenyl)-2-(4-pyridyl)ethanone 
• 403-43-0 4-fluorobenzoyl chloride 

Relevant articles and documents

Treatment for CNS injuries

The present invention is directed to the use of 2,4,5-trisubstituted imidazole compounds and compositions in the treatment of CNS injuries to the brain.

Substituted imidazoles as glucagon receptor antagonists

A modestly active, nonselective triarylimidazole lead was optimized for binding affinity with the human glucagon receptor. This led to the identification of a 2- and/or 4-alkyl or alkyloxy substituent on the imidazole C4-aryl group as a structural determinant for significant enhancement in binding with the glucagon receptor (e.g., 41, IC50 = 0.053 μM) and selectivity (> 1000 ×) over p38 MAP kinase in this class of compounds.

Pyridyl imidazoles

Novel 2,4,5-triaryl imidazole compounds and compositions for use in therapy.