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

Base Information

• Chemical Name: 4-(4-Fluorophenyl)-2-(4-methylsulfinylphenyl)-5-(4-pyridyl)-1H-imidazole
• CAS No.: 152121-47-6
• Molecular Formula: C21H16FN3OS
• Molecular Weight: 377.442
• Hs Code.: 29333990
• European Community (EC) Number: 688-252-3
• UNII: OU13V1EYWQ
• DSSTox Substance ID: DTXSID2040577
• Nikkaji Number: J654.606D
• Wikipedia: SB_203580
• Wikidata: Q7389023
• NCI Thesaurus Code: C179071
• Pharos Ligand ID: 12QG2TP71AWM
• Metabolomics Workbench ID: 121243
• ChEMBL ID: CHEMBL10
• Mol file: 152121-47-6.mol

Synonyms:4-(4-fluorophenyl)-2-(4-methylsulfinylphenyl)-5-(4-pyridyl)-1H-imidazole;pyridine, 4-(5-(4-fluorophenyl)-2-(4-(methylsulfinyl)phenyl)-1H-imidazol-4-yl)-;SB 203580;SB-203580;SB203580

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

Chemical Property:

• Appearance/Colour: White to off-white solid
• Vapor Pressure: 2E-14mmHg at 25°C
• Melting Point: 144-146
• Refractive Index: 1.714
• Boiling Point: 615.6 °C at 760 mmHg
• PKA: 9.60±0.10(Predicted)
• Flash Point: 326.1 °C
• PSA: 77.85000
• Density: 1.42 g/cm³
• LogP: 5.54790
• Storage Temp.: −20°C
• Solubility.: DMSO: 50 mg/mL
• XLogP3: 3.2
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 4
• Exact Mass: 377.09981148
• Heavy Atom Count: 27
• Complexity: 500

Purity/Quality:

99% ^*data from raw suppliers

SB 203580 ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xn
• Hazard Codes: Xn
• Statements: 22-41
• Safety Statements: 26-39

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: CS(=O)C1=CC=C(C=C1)C2=NC(=C(N2)C3=CC=NC=C3)C4=CC=C(C=C4)F
• Description: SB 203580 (152121-47-6) is a potent and selective inhibitor of p38 MAP kinase, IC50=50 and 500 nM for p38 and p38β2 respectively.1 No other kinases (in a panel of 30) were significantly inhibited including p38γ and δ at 10 μM.2?A potent inhibitor of inflammatory cytokine production (IC50=15-25 mg/kg in mice and rats) in animal models of arthritis, bone resorption, endotoxin shock and immune function.3
• Uses: A pyridinyl imidazole which acts as a specific inhibitor of p38 MAP kinase. Does not inhibit the MAP kinase homologs JNK and p42 MAP kinase A p38 MAPK inhibitor with an IC50 range of 0.3-0.5 μM and blocks PKB phosphorylation with an IC50 range of 3-5 μM. MDCK cells were treated with SB 203580 to study the role of MAPK signaling in inducing hypertonicity of cell membrane and potassium depletion.16 It was used to inhibit MAPK signaling in mouse cortical neurons17 and human hepatocellular carcinoma cell lines.18

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

There total 9 articles about 4-(4-Fluorophenyl)-2-(4-methylsulfinylphenyl)-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: 78.0%

conc. NH4 OH + K2 S2 O8 + 4-(4-Fluorophenyl)-2-(4-methylthiophenyl)-5-(pyridin-4-yl)-1H-imidazole (152121-44-3) → 4-[4-(4-fluorophenyl)-2-(4-methylsulfinylphenyl)-1H-imidazol-5-yl]pyridine (152121-47-6)

Guidance literature:

In water; acetic acid;

Reference yield: 78.0%

4-(4-Fluorophenyl)-2-(4-methylphiophenyl)-5-(4-pyridyl)-1H-imidazole + conc. NH4 OH + K2 S2 O8 + 4-(4-Fluorophenyl)-2-(4-methylthiophenyl)-5-(pyridin-4-yl)-1H-imidazole (152121-44-3) → 4-[4-(4-fluorophenyl)-2-(4-methylsulfinylphenyl)-1H-imidazol-5-yl]pyridine (152121-47-6)

Guidance literature:

In water; acetic acid;

Reference yield: 78.0%

4-(4-Fluorophenyl)-2-(4-methylthiophenyl)-5-(pyridin-4-yl)-1H-imidazole (152121-44-3) → 4-[4-(4-fluorophenyl)-2-(4-methylsulfinylphenyl)-1H-imidazol-5-yl]pyridine (152121-47-6)

Guidance literature:

With dipotassium peroxodisulfate; acetic acid; for 18h;

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

upstream raw materials:

4-(4-Fluorophenyl)-2-(4-methylthiophenyl)-5-(pyridin-4-yl)-1H-imidazole

pyridine-4-methanol

4-fluorobenzoyl chloride

4-fluoro-N-methoxy-N-methylbenzamide