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

Base Information

• Chemical Name: 4-(4-Fluorophenyl)-2-(4-nitrophenyl)-5-(4-pyridyl)-1H-imidazole
• CAS No.: 152121-53-4
• Molecular Formula: C20H13FN4O2
• Molecular Weight: 360.347
• Hs Code.: 2933399990
• European Community (EC) Number: 633-972-5
• UNII: GX3Y2V80CV
• DSSTox Substance ID: DTXSID8042684
• Nikkaji Number: J1.342.800J
• Wikidata: Q27088275
• Pharos Ligand ID: 1W1SNXBP55ND
• ChEMBL ID: CHEMBL17331
• Mol file: 152121-53-4.mol

Synonyms:2-(4-nitrophenyl)-4-(4-fluorophenyl)-5-(4-pyridinyl)-1H-imidazole;4-(4-fluorophenyl)-2-(4-nitrophenyl)-5-(4-pyridyl)-1H-imidazole;PD 169316;PD-169316;PD168316;PD169316

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

Chemical Property:

• Appearance/Colour: Light yellow liquid
• Boiling Point: 583.1 °C at 760 mmHg
• PKA: 9.09±0.10(Predicted)
• Flash Point: 306.4 °C
• PSA: 87.39000
• Density: 1.345 g/cm³
• LogP: 5.37620
• Storage Temp.: 2-8°C
• Solubility.: DMSO: >10mg/mL
• XLogP3: 3.9
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 3
• Exact Mass: 360.10225383
• Heavy Atom Count: 27
• Complexity: 495

Purity/Quality:

99% ^*data from raw suppliers

PD 169316 ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xn
• Hazard Codes: Xn
• Statements: 22-37/38-41
• Safety Statements: 26-39

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)[N+](=O)[O-]
• Description: p38 is a member of the mitogen-activated protein kinase (MAPK) superfamily of enzymes that play an important role in signal transduction. PD 169316 is a selective inhibitor of p38 MAPK. It inhibits p38 MAPK with an IC50 of 89 nM, whereas the IC50s are >100-fold higher for extracellular signal-regulated kinase (ERK) and >1,000-fold higher for protein kinase A (PKA) and PKCα. PD 169316 inhibits apoptosis of neuronal and non-neuronal cells deprived of specific trophic factors such as potassium or nerve growth factor.
• Uses: PD 169316 is a highly selective, potent inhibitor of p38 MAP kinase. PD 169316 inhibits transforming growth factor β-induced Smad signaling in human ovarian cancer cells. PD 169316 acts as an an endogenous suppressor of apoptosis by mimicking CD9, a membrane tetraspanin. Studies show that PD 169316 reduces myocardial ischemia/reperfusion induced voltage-dependent anion channel(VDAC) phosphorylation PD 169316 has been used for the inhibition of p38 enzyme in human hepatocytes. It has been used in culture media to promote embryoid bodies differentiation.

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

There total 7 articles about 4-(4-Fluorophenyl)-2-(4-nitrophenyl)-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:

1-(4-fluorophenyl)-2-pyridin-2-yl-ethane-1,2-dione oxime + 4-nitrobenzaldehdye (555-16-8) → 4-(4-fluorophenyl)-2-(4-nitrophenyl)-5-(4-pyridyl)-1H-imidazole (152121-53-4)

Guidance literature:

Reference yield:

pyridine-4-methanol (586-95-8) → 4-(4-fluorophenyl)-2-(4-nitrophenyl)-5-(4-pyridyl)-1H-imidazole (152121-53-4)

Guidance literature:

Multi-step reaction with 3 steps

1: 97 percent / imidazole / dimethylformamide / 18 h / Ambient temperature

2: 1.) LDA / 1.) THF, hexane, -20 deg C, 45 min, 2.) THF, hexane, from -20 deg C to RT, 2.5 h

3: NH₄OAc, Cu(OAc)2*H₂O, CH₃CO₂H / 0.67 h / 98 °C

With 1H-imidazole; copper diacetate; ammonium acetate; acetic acid; lithium diisopropyl amide; In N,N-dimethyl-formamide;

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

Reference yield:

4-fluorobenzoyl chloride (403-43-0) → 4-(4-fluorophenyl)-2-(4-nitrophenyl)-5-(4-pyridyl)-1H-imidazole (152121-53-4)

Guidance literature:

Multi-step reaction with 3 steps

1: 100 percent / Et₃N / CH₂Cl₂ / 0.5 h

2: 1.) LDA / 1.) THF, hexane, -20 deg C, 45 min, 2.) THF, hexane, from -20 deg C to RT, 2.5 h

3: NH₄OAc, Cu(OAc)2*H₂O, CH₃CO₂H / 0.67 h / 98 °C

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

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

upstream raw materials:

4-nitrobenzaldehdye

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

pyridine-4-methanol

4-fluorobenzoyl chloride

Downstream raw materials:

2-(4-Aminophenyl)-4-(4-fluorophenyl)-5-(pyridin-4-yl)-1H-imidazole

Refernces

• 1、 -. "Treatment for CNS injuries". . . Retrieved 2008/06/13.
• 2、 -. "Pyrimidinyl imidazoles". . . Retrieved 2008/06/13.