4-[4-(4-fluorophenyl)-2-(4-nitrophenyl)-1H-imidazol-5-yl]pyridine

• ChemBase ID: 154326
• Molecular Formular: C20H13FN4O2
• Molecular Mass: 360.3412232
• Monoisotopic Mass: 360.1022539
• SMILES: c1cc(ccc1c1[nH]c(c(n1)c1ccc(cc1)F)c1ccncc1)[N+](=O)[O-]
• Canonical SMILES: Fc1ccc(cc1)c1nc([nH]c1c1ccncc1)c1ccc(cc1)[N+](=O)[O-]
• InChI: InChI=1S/C20H13FN4O2/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(8-4-15)25(26)27/h1-12H,(H,23,24)
• InChIKey: BGIYKDUASORTBB-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 4-[4-(4-fluorophenyl)-2-(4-nitrophenyl)-1H-imidazol-5-yl]pyridine; 4-[5-(4-fluorophenyl)-2-(4-nitrophenyl)-1H-imidazol-4-yl]pyridine
• IUPAC Traditional name: 4-[5-(4-fluorophenyl)-2-(4-nitrophenyl)-3H-imidazol-4-yl]pyridine; 4-[5-(4-fluorophenyl)-2-(4-nitrophenyl)-1H-imidazol-4-yl]pyridine
• Synonyms: 4-(4-Fluorophenyl)-2-(4-nitrophenyl)-5-(4-pyridyl)-1H-imidazole; PD 169316; 4-[4-(4-fluorophenyl)-2-(4-nitrophenyl)-1H-imidazol-5-yl]pyridine; 4-[5-(4-fluorophenyl)-2-(4-nitrophenyl)-1H-imidazol-4-yl]pyridine; PD-169316

Database IDs

• CAS Number: 152121-53-4
• MDL Number: MFCD12405019
• PubChem SID: 162248465; 24278156
• PubChem CID: 4712

CALCULATED PROPERTIES

• Acid pKa: 11.798662
• H Acceptors: 4
• H Donor: 1
• LogD (pH = 5.5): 4.2508125
• LogD (pH = 7.4): 4.3435416
• Log P: 4.344862
• Molar Refractivity: 109.2765 cm^3
• Polarizability: 39.916897 Å^3
• Polar Surface Area: 87.39 Å^2
• Rotatable Bonds: 4
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: DMSO: >10 mg/mL; H2O: insoluble
• Apperance: light orange solid

Safety Information

• European Hazard Symbols: Harmful (Xn)
• UN Number: 2811
• German water hazard class: 3
• Hazard Class: 6.1
• Packing Group: 3
• Risk Statements: 22-37/38-41
• Safety Statements: 26-39
• GHS Pictograms: GHS05; GHS06
• GHS Signal Word: Danger
• GHS Hazard statements: H301-H315-H318-H335
• GHS Precautionary statements: P261-P280-P301 + P310-P305 + P351 + P338
• Personal Protective Equipment: dust mask type N95 (US), Eyeshields, Faceshields, Gloves
• RID/ADR: UN 2811 6.1/PG 3
• Storage Temperature: 2-8°C

Pharmacology Properties

• Gene Information: human ... MAPK14(1432)

Product Information

• Purity: ≥98% (HPLC)
• Empirical Formula (Hill Notation): C20H13FN4O2

DETAILS

Sigma Aldrich - P9248

Biochem/physiol Actions
Potent, cell-permeable and selective p38 MAP kinase inhibitor (IC50 = 89 nM).

Toronto Research Chemicals - P217600

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 membr

REFERENCES

• Fu, Y. et al.: Bioche,. Biophys. Res. Comm., 310, 391 (2003)
• Krishnamoorthy, M. et al.: J. Biochem., 145, 177 (2003)
• Schwertz, H. et al.: Proteomics, 7, 24 (2003)