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356559-20-1 分子结构
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6-[2-tert-butyl-5-(6-methylpyridin-2-yl)-1H-imidazol-4-yl]quinoxaline

ChemBase编号:72700
分子式:C21H21N5
平均质量:343.42494
单一同位素质量:343.1796957
SMILES和InChIs

SMILES:
c1(ccc2c(c1)nccn2)c1[nH]c(nc1c1cccc(n1)C)C(C)(C)C
Canonical SMILES:
Cc1cccc(n1)c1nc([nH]c1c1ccc2c(c1)nccn2)C(C)(C)C
InChI:
InChI=1S/C21H21N5/c1-13-6-5-7-16(24-13)19-18(25-20(26-19)21(2,3)4)14-8-9-15-17(12-14)23-11-10-22-15/h5-12H,1-4H3,(H,25,26)
InChIKey:
DKPQHFZUICCZHF-UHFFFAOYSA-N

引用这个纪录

CBID:72700 http://www.chembase.cn/molecule-72700.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
6-[2-tert-butyl-5-(6-methylpyridin-2-yl)-1H-imidazol-4-yl]quinoxaline
6-[2-tert-butyl-4-(6-methylpyridin-2-yl)-1H-imidazol-5-yl]quinoxaline
IUPAC传统名
6-[2-tert-butyl-5-(6-methylpyridin-2-yl)-1H-imidazol-4-yl]quinoxaline
6-[2-tert-butyl-5-(6-methylpyridin-2-yl)-3H-imidazol-4-yl]quinoxaline
别名
6-[2-tert-butyl-5-(6-methyl-pyridin-2-yl)-1H-imidazol-4-yl]-quinoxaline
SB-525334
SB 525334
6-[2-(1,1-Dimethylethyl)-5-(6-methyl-2-pyridinyl)-1H-imidazol-4-yl]quinoxaline
SB-525334
CAS号
356559-20-1
MDL号
MFCD11045307
PubChem SID
162037621
PubChem CID
9967941

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 9967941 external link

理论计算性质

理论计算性质

JChem
Acid pKa 11.831985  质子受体
质子供体 LogD (pH = 5.5) 3.8246043 
LogD (pH = 7.4) 4.0002885  Log P 4.00306 
摩尔折射率 100.3888 cm3 极化性 43.104168 Å3
极化表面积 67.35 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: ≥20 mg/mL expand 查看数据来源
外观
yellow solid 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
有害性(Harmful) 有害性(Harmful) (Xn) expand 查看数据来源
联合国危险货物编号
2811 expand 查看数据来源
MSDS下载
下载链接 expand 查看数据来源
下载链接 expand 查看数据来源
德国WGK号
3 expand 查看数据来源
联合国危险货物等级
6.1 expand 查看数据来源
联合国危险货物包装类别(PG)
3 expand 查看数据来源
危险公开号
22-36/37/38 expand 查看数据来源
安全公开号
26 expand 查看数据来源
GHS危险品标识
GHS06 expand 查看数据来源
GHS警示词
Danger expand 查看数据来源
GHS危险声明
H301-H315-H319-H335-H413 expand 查看数据来源
GHS警示性声明
P261-P301 + P310-P305 + P351 + P338 expand 查看数据来源
个人保护装置
dust mask type N95 (US), Eyeshields, Faceshields, Gloves expand 查看数据来源
RID/ADR
UN 2811 6.1/PG 3 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
ALK 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
质检报告
下载链接 expand 查看数据来源
Empirical Formula (Hill Notation)
C21H21N5 expand 查看数据来源

详细说明

详细说明

Selleck Chemicals Selleck Chemicals Sigma Aldrich Sigma Aldrich TRC TRC
Selleck Chemicals -  S1476 external link
Research Area
Description Cancer
Biological Activity
Description SB 525334 is a potent and selective inhibitor of TGF-β1 (ALK5) with IC50 of 14.3 nM.
Targets TGF-β1 (ALK5)
IC50 14.3 nM [1]
In Vitro SB 525334 shows no inhibition in the enzymes ALK2, 3, and 6, with IC50 values > 10 μM. SB 525334 blocks phosphorylation induced by TGF-β1 and nuclear translocation of Smad2/3 in renal proximal tubule cells. SB 525334 also inhibits the increased mRNA expression levels of plasminogen activator inhibitor-1 (PAI-1) and procollagen α1(I) induced by TGF-β1 in A498 renal epithelial carcinoma cells at 1 μM). [1]SB 525334 (1 μM) attenuates the heightened sensitivity to TGF-β1 exhibited by pulmonary artery smooth muscle cells (PASMCs) from patients with familial forms of idiopathic pulmonary arterial hypertension (PAH). [2]
In Vivo SB 525334 (10 mg/kg/day) decreases the renal mRNA levels of PAI-1, procollagen α1(I), and procollagen α1(III) in a nephritis-induced renal fibrosis rat model. Furthermore, PAN-induced proteinuria is significantly inhibited by SB 525334 (10 mg/kg/day). [1]SB 525334 may also be efficacious in mesenchymal tumors. SB 525334 (10 mg/kg/day) significantly decreases uterine mesenchymal tumor incidence, multiplicity, and size in Eker rats. [3]SB 525334 significantly reverses pulmonary arterial pressure and inhibits right ventricular hypertrophy in a rat model of PAH. This is revealed by a significant reduction in pulmonary arteriole muscularization induced by monocrotaline (used to induce PAH) after treatment with SB 525334 (3 or 30 mg/kg). [2]In a Bleomycin-induced pulmonary fibrosis mice model, SB 525334 (10 mg/kg or 30 mg/kg) attenuates the histopathological alterations in the lung, and significantly decreased mRNA expression of Type I and III procollagen and fibronectin. SB 525334 also attenuates Smad2/3 nuclear translocation, myofibroblast proliferation, deposition of Type I collagen, and decreases CTGF-expressing cells. [4]
Clinical Trials
Features
Protocol
Kinase Assay [1]
Kinase assay to determine the potency and selectivity of SB 525334 In order to determine the potency of SB 525334, purified GST-tagged kinase domain of ALK5 is incubated with purified GST-tagged full-length Smad3 in the presence of 33P-γATP and different concentrations of SB 525334. The readout is radioactively labeled Smad3.To determine the selectivity of SB 525334, purified GST-tagged kinase domain of ALK2 and ALK4 are incubated with GST-tagged full-length Smad1 and Smad3, respectively, in the presence of different concentrations of SB 525334. IC50 values are calculated.
Cell Assay [1]
Cell Lines Human renal proximal tubule epithelial (RPTE) cells
Concentrations 1 μM
Incubation Time 1 hour
Methods RPTE cells are seeded on microscope slides. The following day, the cells are starved for 24 hours to dosing by removal of the serum and epidermal growth factor. Cells are treated with either 10 ng/mL TGF-β1, 1 μM SB 525334, or a combination of both. Slides are pretreated with SB 525334 or starve media for 3 hours prior to a 1-hour incubation at 37 °C with TGF-β1 or starve media.The cells are then fixed and permeabilized. The slides are blocked with BSA, incubated with a mouse anti-Smad2/3 primary antibody followed by an anti-mouse IgG fluorescein secondary antibody. The slides are then viewed in a confocal microscope and nuclear signal intensity is analyzed.
Animal Study [3]
Animal Models Bleomycin-induced pulmonary fibrosis in female Eker rats
Formulation 200 mg/L in drinking water
Doses Estimated dose of 10 mg/kg/day
Administration Oral (in drinking water)
References
[1] Grygielko ET, et al. J Pharmacol Exp Ther, 2005, 313(3), 943-951.
[2] Thomas M, et al. Am J Pathol, 2009, 174(2), 380-389.
[3] Laping NJ, et al. Clin Cancer Res, 2007, 13(10), 3087-3899.
[4] Higashiyama H, et al. Exp Mol Pathol, 2007, 83(1), 39-46.
Sigma Aldrich -  S8822 external link
Biochem/physiol Actions
SB-525334 is a potent activin receptor-like kinase (ALK5)/ type I TGFβ-receptor kinase inhibitor with IC50 = 14.3 nM.
Toronto Research Chemicals -  S154700 external link
SB-525334 is a potent activin receptor-like kinase (ALK5)/ type I TGFβ-receptor kinase inhibitor with IC50 = 14.3 nM.

参考文献

参考文献

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