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(3R)-3-cyclopentyl-3-(4-{7H-pyrrolo[2,3-d]pyrimidin-4-yl}-1H-pyrazol-1-yl)propanenitrile

ChemBase编号:73153
分子式:C17H18N6
平均质量:306.36502
单一同位素质量:306.15929461
SMILES和InChIs

SMILES:
n1cnc2c(c1c1cn(nc1)[C@@H](C1CCCC1)CC#N)cc[nH]2
Canonical SMILES:
N#CC[C@@H](n1ncc(c1)c1ncnc2c1cc[nH]2)C1CCCC1
InChI:
InChI=1S/C17H18N6/c18-7-5-15(12-3-1-2-4-12)23-10-13(9-22-23)16-14-6-8-19-17(14)21-11-20-16/h6,8-12,15H,1-5H2,(H,19,20,21)/t15-/m1/s1
InChIKey:
HFNKQEVNSGCOJV-OAHLLOKOSA-N

引用这个纪录

CBID:73153 http://www.chembase.cn/molecule-73153.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
(3R)-3-cyclopentyl-3-(4-{7H-pyrrolo[2,3-d]pyrimidin-4-yl}-1H-pyrazol-1-yl)propanenitrile
IUPAC传统名
(3R)-3-cyclopentyl-3-(4-{7H-pyrrolo[2,3-d]pyrimidin-4-yl}pyrazol-1-yl)propanenitrile
别名
Ruxolitinib
INCB018424
(βR)-β-Cyclopentyl-4-(7H-pyrrolo[2,3-d]pyrimidin-4-yl)-1H-pyrazole-1-propanenitrile
INCB 018424
(R)-Ruxolitinib
CAS号
941678-49-5
PubChem SID
162038073
PubChem CID
25126798

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 25126798 external link

理论计算性质

理论计算性质

JChem
Acid pKa 13.89365  质子受体
质子供体 LogD (pH = 5.5) 2.1799238 
LogD (pH = 7.4) 2.4738674  Log P 2.4793217 
摩尔折射率 98.0065 cm3 极化性 34.707794 Å3
极化表面积 83.18 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

安全信息 药理学性质 产品相关信息 生物活性(PubChem)
保存条件
-20°C expand 查看数据来源
MSDS下载
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作用靶点
JAK expand 查看数据来源
成盐信息
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质检报告
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详细说明

详细说明

Selleck Chemicals Selleck Chemicals TRC TRC
Selleck Chemicals -  S1378 external link
Protocol
Kinase Assay [2]
Biochemical assays The kinase domains of human JAK1 (837-1142), JAK2 (828-1132), JAK3 (781-1124), and Tyk2 (873-1187) are cloned by PCR with N-terminal epitope tags. Recombinant proteins are expressed using Sf21 cells and baculovirus vectors and purified with affinity chromatography. JAK kinase assays used a homogeneous time-resolved fluorescence assay with the peptide substrate (-EQEDEPEGDYFEWLE). Each enzyme reaction is carried out with INCB018424 or control, JAK enzyme, 500 nM peptide, adenosine triphosphate (ATP; 1 mM), and 2.0% dimethyl sulfoxide (DMSO) for 1 hour. The 50% inhibitory concentration (IC50) is calculated as the compound concentration required for inhibition of 50% of the fluorescent signal. Biochemical assays for CHK2 and c-MET enzymes are performed using standard conditions (Michaelis constant [Km] ATP) with recombinantly expressed catalytic domains from each protein and synthetic peptide substrates. An additional panel of kinase assays (Abl, Akt1, AurA, AurB, CDC2, CDK2, CDK4, CHK2, c-kit, c-Met, GFR, EphB4, ERK1, ERK2, FLT-1, HER2, IGF1R, IKKα, IKKβ, JAK2, JAK3, JNK1, Lck, MEK1, p38α, p70S6K, PKA, PKCα, Src, and ZAP70) is performed using standard conditions using 200 nM INCB018424. Significant inhibition is defined as more than or equal to 30% (average of duplicate assays) compared with control values.
Cell Assay [2]
Cell Lines Ba/F3-EpoR-JAK2V617F or HEL cells
Concentrations 0-4 nM
Incubation Time 48 hours
Methods Ba/F3-EpoR-JAK2V617F or HEL cells are seeded at 2000/well of white bottom 96-well plates, treated with INCB018424 from DMSO stocks (0.2% final DMSO concentration), and incubated for 48 hours at 37 °C with 5% CO2. Viability is measured by cellular ATP determination using the Cell-Titer Glo luciferase reagent or viable cell counting. Values are transformed to percent inhibition relative to vehicle control, and IC50 curves are fitted according to nonlinear regression analysis of the data.
Animal Study [2]
Animal Models 6- to 8-week-old female BALB/c mice with Ba/F3-JAK2V617F tumors
Formulation 5% dimethyl acetamide, 0.5% methocellulose
Doses 180 mg/kg
Administration Oral gavage
References
[1] Williams WV, et al. Ann Rheum Dis. 2008, 67(Suppl II), 62.
[2] Quintás-Cardama A, et al.Blood. 2010, 115(15), 3109-3117.
Toronto Research Chemicals -  R702000 external link
Ruxolitinib is a selective Janus tyrosine kinase (JAK1 and JAK2) inhibitor used in the treatment of myeloproliferative neoplasms and psoriasis.

参考文献

参考文献

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专利

专利

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