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405554-55-4 分子结构
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[2-(4-{5-[(1E)-1-(hydroxyimino)-2,3-dihydro-1H-inden-5-yl]-4-(pyridin-4-yl)-1H-imidazol-2-yl}phenoxy)ethyl]dimethylamine

ChemBase编号:72908
分子式:C27H27N5O2
平均质量:453.53558
单一同位素质量:453.21647513
SMILES和InChIs

SMILES:
n1c(c([nH]c1c1ccc(cc1)OCCN(C)C)c1ccc2c(c1)CC/C/2=N\O)c1ccncc1
Canonical SMILES:
O/N=C/1\CCc2c1ccc(c2)c1[nH]c(nc1c1ccncc1)c1ccc(cc1)OCCN(C)C
InChI:
InChI=1S/C27H27N5O2/c1-32(2)15-16-34-22-7-3-19(4-8-22)27-29-25(18-11-13-28-14-12-18)26(30-27)21-5-9-23-20(17-21)6-10-24(23)31-33/h3-5,7-9,11-14,17,33H,6,10,15-16H2,1-2H3,(H,29,30)/b31-24+
InChIKey:
MLSAQOINCGAULQ-QFMPWRQOSA-N

引用这个纪录

CBID:72908 http://www.chembase.cn/molecule-72908.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
[2-(4-{5-[(1E)-1-(hydroxyimino)-2,3-dihydro-1H-inden-5-yl]-4-(pyridin-4-yl)-1H-imidazol-2-yl}phenoxy)ethyl]dimethylamine
IUPAC传统名
[2-(4-{4-[(1E)-1-(hydroxyimino)-2,3-dihydroinden-5-yl]-5-(pyridin-4-yl)-3H-imidazol-2-yl}phenoxy)ethyl]dimethylamine
别名
SB 590885
SB590885
CAS号
405554-55-4
PubChem SID
162037828
PubChem CID
11316960

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 价格
Selleck Chemicals
S2220 external link 加入购物车 请登录
数据来源 数据ID
PubChem 11316960 external link

理论计算性质

理论计算性质

JChem
Acid pKa 8.433906  质子受体
质子供体 LogD (pH = 5.5) 0.84019864 
LogD (pH = 7.4) 2.621574  Log P 3.3556507 
摩尔折射率 143.7071 cm3 极化性 54.187893 Å3
极化表面积 86.63 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
作用靶点
B-Raf expand 查看数据来源
成盐信息
Free Base expand 查看数据来源

详细说明

详细说明

Selleck Chemicals Selleck Chemicals
Selleck Chemicals -  S2220 external link
Research Area
Description Cancer
Biological Activity
Description SB590885 is a potent B-Raf inhibitor with Ki of 0.16 nM.
Targets B-Raf
IC50 0.16 nM (Ki) [1]
In Vitro SB590885 displays significant selectivity for B-Raf over c-Raf with Ki of 0.16 nM over 1.72 nM. SB-590885 is a more potent inhibitor than the previously described Raf/VEGFR kinase inhibitor BAY 439006 (Ki = 38 nM for mutant B-Raf, 6 nM for c-Raf). SB590885 displays potent selectivity over 46 other kinases. Unlike the multi-kinase inhibitor BAY43-9006, SB590885 stabilizes the oncogenic B-Raf kinase domain in an active configuration. In Colo205, HT29, A375P, SKMEL28, and MALME-3M cells expressing oncogenic B-RafV600E, SB590885 treatment potently inhibits ERK phosphorylation with EC50 of 28 nM, 58 nM, 290 nM, 58 nM, and 190 nM, respectively, and consistently, inhibits the proliferation with EC50 of 0.1 μM, 0.87 μM, 0.37 μM, 0.12 μM, and 0.15 μM, respectively. SB590885 decreases anchorage-independent growth of melanoma cell lines in a BRAF mutant-selective manner. [1] SB590885 displays high affinity for B-Raf with Kd of 0.3 nM. [2] Most of the melanoma cell lines that harbor the BRAF V600E mutation and lack CDK4 mutations (451Lu, WM35, and WM983) are highly sensitive to SB590885 with IC50 of <1 μm.="" increased="" levels="" of="" cyclin="" d1="" resulting="" from="" genomic="" amplification="" mediate="" sb590885="" resistance="" in="" b-raf="" v600e-mutated="" melanomas.="">[3]
In Vivo Administration of SB590885 potently decreases tumorigenesis in murine xenografts established from mutant B-Raf-expressing A375P melanoma cells, and modestly inhibits tumor growth. [1]
Clinical Trials
Features SB590885 displays significant selectivity for B-Raf over c-Raf.
Protocol
Cell Assay [1]
Cell Lines Colo205, HT29, A375P, SKMEL28, and MALME-3M
Concentrations Dissolved in DMSO, final concentrations ~10 μM
Incubation Time 72 hours
Methods Cells are treated with increasing concentrations of SB590885 and incubated for 72 hours. Viable cells are quantified using CellTiter-Glo reagent and luminescence detection on a Victor 2V plate reader. Cells are prepared for cell cycle analysis on a Becton Dickinson FACScan. Data is acquired and analyzed using CellQuest v3.3 software.
Animal Study [1]
Animal Models Female nude mice injected s.c. with of A375P cells
Formulation Dissolved in vehicle [2% N,N-dimethylacetamide, 2% Cremophor EL, and 96% acidified water (pH f4–5)]
Doses 50 mg/kg/day
Administration Injection i.p.
References
[1] King AJ, et al. Cancer Res, 2006, 66(23), 11100-11105.
[2] Takle AK, et al. Bioorg Med Chem Lett, 2006, 16(2), 378-381.
[3] Smalley KS, et al. Mol Cancer Ther, 2008, 7(9), 2876-2883.

参考文献

参考文献

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专利

专利

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