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152121-30-7 分子结构
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4-[4-(4-fluorophenyl)-5-(pyridin-4-yl)-1H-imidazol-2-yl]phenol

ChemBase编号:72494
分子式:C20H14FN3O
平均质量:331.3430632
单一同位素质量:331.1120903
SMILES和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

引用这个纪录

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

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名称和登记号

名称和登记号

名称 登记号
IUPAC标准名
4-[4-(4-fluorophenyl)-5-(pyridin-4-yl)-1H-imidazol-2-yl]phenol
IUPAC传统名
4-[4-(4-fluorophenyl)-5-(pyridin-4-yl)-1H-imidazol-2-yl]phenol
别名
SB 202190
4-(4-Fluorophenyl)-2-(4-hydroxyphenyl)-5-(4-pyridyl)-1H-imidazole
SB 202190
CAS号
152121-30-7
MDL号
MFCD00941964
PubChem SID
24278272
162037419
PubChem CID
5353940

数据来源

数据来源

所有数据来源 商品来源 非商品来源
数据来源 数据ID
PubChem 5353940 external link

理论计算性质

理论计算性质

JChem
Acid pKa 9.645799  质子受体
质子供体 LogD (pH = 5.5) 3.9184663 
LogD (pH = 7.4) 4.096198  Log P 4.1013126 
摩尔折射率 103.9327 cm3 极化性 38.711132 Å3
极化表面积 61.8 Å2 可自由旋转的化学键
里宾斯基五规则 true 

分子性质

分子性质

理化性质 安全信息 药理学性质 产品相关信息 生物活性(PubChem)
溶解度
DMSO expand 查看数据来源
DMSO: soluble30 mg/mL expand 查看数据来源
外观
pale yellow expand 查看数据来源
保存条件
-20°C expand 查看数据来源
欧盟危险性物质标志
刺激性(Irritant) 刺激性(Irritant) (Xi) expand 查看数据来源
MSDS下载
下载链接 expand 查看数据来源
德国WGK号
3 expand 查看数据来源
危险公开号
36/37/38 expand 查看数据来源
安全公开号
26-36/37 expand 查看数据来源
GHS危险品标识
GHS07 expand 查看数据来源
GHS警示词
Warning expand 查看数据来源
GHS危险声明
H315-H319-H335 expand 查看数据来源
GHS警示性声明
P261-P305 + P351 + P338 expand 查看数据来源
个人保护装置
dust mask type N95 (US), Eyeshields, Gloves expand 查看数据来源
保存温度
2-8°C expand 查看数据来源
作用靶点
p38 MAPK expand 查看数据来源
相关基因信息
human ... MAPK14(1432) expand 查看数据来源
纯度
≥98% (HPLC) expand 查看数据来源
成盐信息
Free Base expand 查看数据来源
Empirical Formula (Hill Notation)
C20H14FN3O expand 查看数据来源

详细说明

详细说明

Sigma Aldrich Sigma Aldrich Selleck Chemicals Selleck Chemicals
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
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.

专利

专利

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