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152121-30-7 molecular structure
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4-[4-(4-fluorophenyl)-5-(pyridin-4-yl)-1H-imidazol-2-yl]phenol

ChemBase ID: 72494
Molecular Formular: C20H14FN3O
Molecular Mass: 331.3430632
Monoisotopic Mass: 331.1120903
SMILES and InChIs

SMILES:
c1c(ccc(c1)c1nc([nH]c1c1ccncc1)c1ccc(cc1)O)F
Canonical SMILES:
Oc1ccc(cc1)c1nc(c([nH]1)c1ccncc1)c1ccc(cc1)F
InChI:
InChI=1S/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/h1-12,25H,(H,23,24)
InChIKey:
QHKYPYXTTXKZST-UHFFFAOYSA-N

Cite this record

CBID:72494 http://www.chembase.cn/molecule-72494.html

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NAMES AND DATABASE IDS

NAMES AND DATABASE IDS

Names Database IDs
IUPAC name
4-[4-(4-fluorophenyl)-5-(pyridin-4-yl)-1H-imidazol-2-yl]phenol
IUPAC Traditional name
4-[4-(4-fluorophenyl)-5-(pyridin-4-yl)-1H-imidazol-2-yl]phenol
Synonyms
4-(4-Fluorophenyl)-2-(4-hydroxyphenyl)-5-(4-pyridyl)-1H-imidazole
SB 202190
SB 202190
4-(4-fluorophenyl)-2-(4-hydroxyphenyl)-5-(4-pyridyl)-1h-imidazole
CAS Number
152121-30-7
MDL Number
MFCD00941964
PubChem SID
162037419
24278272
PubChem CID
5353940

DATA SOURCES

DATA SOURCES

All Sources Commercial Sources Non-commercial Sources
Data Source Data ID
PubChem 5353940 external link

CALCULATED PROPERTIES

CALCULATED PROPERTIES

JChem
Acid pKa 9.645799  H Acceptors
H Donor LogD (pH = 5.5) 3.9184663 
LogD (pH = 7.4) 4.096198  Log P 4.1013126 
Molar Refractivity 103.9327 cm3 Polarizability 38.711132 Å3
Polar Surface Area 61.8 Å2 Rotatable Bonds
Lipinski's Rule of Five true 

PROPERTIES

PROPERTIES

Physical Property Safety Information Pharmacology Properties Product Information Bioassay(PubChem)
Solubility
DMSO expand Show data source
DMSO: soluble30 mg/mL expand Show data source
Apperance
pale yellow expand Show data source
Storage Condition
-20°C expand Show data source
European Hazard Symbols
Irritant Irritant (Xi) expand Show data source
MSDS Link
Download expand Show data source
German water hazard class
3 expand Show data source
Risk Statements
36/37/38 expand Show data source
Safety Statements
26-36/37 expand Show data source
GHS Pictograms
GHS07 expand Show data source
GHS Signal Word
Warning expand Show data source
GHS Hazard statements
H315-H319-H335 expand Show data source
GHS Precautionary statements
P261-P305 + P351 + P338 expand Show data source
Personal Protective Equipment
dust mask type N95 (US), Eyeshields, Gloves expand Show data source
Storage Temperature
2-8°C expand Show data source
Target
p38 MAPK expand Show data source
Gene Information
human ... MAPK14(1432) expand Show data source
Purity
≥98% (HPLC) expand Show data source
97% expand Show data source
Salt Data
Free Base expand Show data source
Empirical Formula (Hill Notation)
C20H14FN3O expand Show data source

DETAILS

DETAILS

Selleck Chemicals Selleck Chemicals Sigma Aldrich Sigma Aldrich
Selleck Chemicals - S1077 external link
Research Area
Description Inflammation
Biological Activity
Description SB 202190 (FHPI) is a potent p38 MAPK inhibitor targeting p38α and p38β with IC50 of 50 nM and 100 nM, respectively.
Targets p38α p38β
IC50 50 nM 100 nM [1]
In Vitro SB 202190 significantly inhibits both basal and anti-Fas antibody-induced MAPKAPK 2 activity in a dose-dependent manner. SB202190 by itself is sufficient to induce cell death in Jurkat and HeLa cells through activation of CPP32-like caspases, which can be blocked by expression of bcl-2. SB202190-induced apoptosis is attenuated by p38β but augmented by p38α. [2] SB 202190 strongly inhibits UVB induced COX-2 protein expression in HaCaT cells, and markedly inhibits UVB induced cox-2 mRNA. [3] SB 202190 treatment inhibits the expression of albumin-induced proinflammatory (monocyte chemoattractant protein-1) and transforming growth factor (TGF)-beta1-induced profibrotic (procollagen-Ialpha1) genes over 50% in renal tubular cells (normal rat kidney-52E). [4] SB 202190 treatment induces phosphorylation of JNK in a dose- and time- dependent manner in A549 cells, induces phosphorylation of ATF-2 transcription factor, and increases AP-1 DNA binding. [6] SB 202190 treatment enhances the growth of THP-1 and MV4-11 cells. SB 202190 increases the phosphorylation of c-Raf and ERK, suggesting that Ras-Raf-MEK-mitogen-activated protein kinase (MAPK) pathway activation is involved in the leukemia cell growth induced by SB 202190. [7]
In Vivo Inhibiting p38 by administration of SB 202190 inhibits PV IgG-induced blister formation in the passive transfer mouse model. [5] In the endotoxin model of sepsis, SB 202190 treatment produces a statistically significant survival benefit compared with control. [8]
Clinical Trials
Features
Combination Therapy
Description The p38 inhibition by SB 202190 sensitizes tumor cells derived from both SN38-sensitive and -resistant HCT116 cells to Irinotecan treatment in xenograft models. [9] SB 202190 significantly decreases the Etoposide-induced ERCC1 protein levels and DNA repair capacity in etoposide-exposed NSCLC cells to sensitize lung cancer cells to Etoposide. [10]
Protocol
Kinase Assay [1]
In vitro kinase assays The p38α and p38β are assayed in 25 mM Tris-HCl, pH 7.5, containing 0.1 mM EGTA, with myelin basic protein (0.33 mg/mL) as substrate. Assays are performed either manually for 10 minutes at 30 °C in 50 μL incubations using [γ-33P]ATP, or with a Biomek 2000 Laboratory Automation Workstation in a 96-well format for 40 minutes at ambient temperature in 25 μL incubations using [γ-33P]ATP. The concentrations of ATP and magnesium acetate are 0.1 mM and 10 mM respectively. All assays are initiated with MgATP. Manual assays are terminated by spotting aliquots of incubation on to phosphocellulose paper, followed by immersion in 50 mM phosphoric acid. Robotic assays are terminated by the addition of 5 μL of 0.5 M phosphoric acid before spotting aliquots on to P30 filter mats. All papers are then washed four times in 50 mM phosphoric acid to remove ATP, once in acetone (manual incubations) or methanol (robotic incubations), and then dried and counted for radioactivity.
Cell Assay [2]
Cell Lines Jurkat, and HeLa
Concentrations Dissolved in DMSO, final concentrations ~50 μM
Incubation Time 24 hours
Methods Cells are serum-starved and then treated with different concentration of SB 202190 for 24 hours. Cell viability is assayed by either trypan blue exclusion or propidium iodide exclusion followed by flow cytometry analysis. The apoptotic nuclei are visualized by H33258 staining.
Animal Study [5]
Animal Models C57BL/6J mice injected i.d. with a sterile solution of either control IgG or PV IgG
Formulation Dissolved in DMSO, and diluted in saline
Doses 12.5 μg
Administration Administered via i.d.
References
[1] Davies SP, et al. Biochem J, 2000, 351(Pt 1), 95-105.
[2] Nemoto S, et al. J Biol Chem, 1998, 273(26), 16415-16420.
[3] Chen W, et al. Oncogene, 2001, 20(29), 3921-3926.
[4] Prakash J, et al. J Pharmacol Exp Ther, 2006, 319(1), 8-19.
[5] Berkowitz P, et al. Proc Natl Acad Sci U S A, 2006, 103(34), 12855-12860.
[6] Muniyappa H, et al. Cell Signal, 2008, 20(4), 675-683.
[7] Hirosawa M, et al. Leuk Res, 2009, 33(5), 693-699.
[8] O'Sullivan AW, et al. J Surg Res, 2009, 152(1), 46-53.
[9] Paillas S, et al. Cancer Res, 2011, 71(3), 1041-1049.
[10] Tsai MS, et al. Mol Cancer Ther, 2012, 11(3), 561-571.
Sigma Aldrich - S7067 external link
Biochem/physiol Actions
SB 202190 is a highly selective, potent and cell permeable inhibitor of p38 MAP kinase. SB 202190 binds within the ATP pocket of the active kinase (Kd = 38 nM, as measured in recombinant human p38), and selectively inhibits the p38α and β isoforms.
Legal Information
Sold for research purposes under agreement from Glaxo-Smith-Kline

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