您当前所在的位置:首页 > 产品中心 > 产品详细信息
209783-80-2 分子结构
点击图片或这里关闭

pyridin-3-ylmethyl N-({4-[(2-aminophenyl)carbamoyl]phenyl}methyl)carbamate

ChemBase编号:72482
分子式:C21H20N4O3
平均质量:376.4085
单一同位素质量:376.15354052
SMILES和InChIs

SMILES:
c1c(ccc(c1)C(=O)Nc1ccccc1N)CNC(=O)OCc1cnccc1
Canonical SMILES:
O=C(OCc1cccnc1)NCc1ccc(cc1)C(=O)Nc1ccccc1N
InChI:
InChI=1S/C21H20N4O3/c22-18-5-1-2-6-19(18)25-20(26)17-9-7-15(8-10-17)13-24-21(27)28-14-16-4-3-11-23-12-16/h1-12H,13-14,22H2,(H,24,27)(H,25,26)
InChIKey:
INVTYAOGFAGBOE-UHFFFAOYSA-N

引用这个纪录

CBID:72482 http://www.chembase.cn/molecule-72482.html

Collapse All Expand All

名称和登记号

名称和登记号

名称 登记号
IUPAC标准名
pyridin-3-ylmethyl N-({4-[(2-aminophenyl)carbamoyl]phenyl}methyl)carbamate
IUPAC传统名
entinostat
别名
Entinostat
SNDX-275
MS-27-275
MS-275
MS-275
Entinostat
N-[[4-[[(2-Aminophenyl)amino]carbonyl]phenyl]methyl]carbamic Acid 3-Pyridinylmethyl Ester
(Pyridin-3-yl)methyl 4-(2-Aminophenylcarbamoyl)benzylcarbamate
MS 27-275
MS 275
MS 275-27
N-(2-Aminophenyl)-4-[N-(pyridine-3-yl-methoxycarbonyl)-aminomethyl]benzamide
SNDX 275
CAS号
209783-80-2
PubChem SID
162037407
PubChem CID
4261
CHEMBL
27759
Chemspider ID
4111
KEGG ID
D09338
维基百科标题
Entinostat

数据来源

数据来源

所有数据来源 商品来源 非商品来源

理论计算性质

理论计算性质

JChem
Acid pKa 12.041615  质子受体
质子供体 LogD (pH = 5.5) 2.2447338 
LogD (pH = 7.4) 2.3060522  Log P 2.3069115 
摩尔折射率 108.2884 cm3 极化性 40.191025 Å3
极化表面积 106.34 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 expand 查看数据来源
Methanol expand 查看数据来源
外观
Yellow Solid expand 查看数据来源
熔点
158-160°C expand 查看数据来源
保存条件
-20°C expand 查看数据来源
Refrigerator expand 查看数据来源
MSDS下载
下载链接 expand 查看数据来源
作用靶点
HDAC 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

详细说明

详细说明

Selleck Chemicals Selleck Chemicals Wikipedia Wikipedia TRC TRC
Selleck Chemicals -  S1053 external link
Research Area
Description Cancer
Biological Activity
Description MS-275 is an HDAC inhibitor of HDAC1 and HDAC3 with IC50 of 0.51 μM and 1.7 μM, respectively.
Targets

HDAC1

HDAC3

IC50

0.51 μM

1.7 μM [2]

In Vitro MS-275 shows inhibitory to HDACs by 2′-amino group. MS-275 induces accumulation of p21 WAF1/CIP1 and gelsolin in K562 cell. MS-275 could reduce S-phase cells and induce G1-phase cells in A2780 cell. MS-275 inhibits the proliferation of human tumor cell lines including A2780, Calu-3, HL-60, K562, St-4, HT-29, KB-3-1, Capan-1, 4-1St and HCT-15 with IC50 from 41.5 nM to 4.71 μM, which due to HAD-inhibition. [1] MS-275 is not sensitive to other HDACs (4, 6, 8 and 10) with IC50 about/above 100 μM. [2] MS-275 shows great inhibition to human leukemia and lymphoma cells, including U937, HL-60, K562, and Jurkat. MS-275 also decreases expression of cyclin D1 and the antiapoptotic proteins Mcl-1 and XIAP. [3]
In Vivo MS-275 exhibits great antitumor activity against human tumor xenografts except HCT-15 at 49 mg/kg. [1] MS-275 demonstrates promising therapeutic potential in both solid and hematologic malignancies, as well as regulation of physiologic and aberrant gene expression. [4] MS-275, combination with IL-2, has great antitumor activity to renal cell carcinoma xenograft model, which due to decreased T regulatory cells and increased splenocytes. [5]
Clinical Trials MS-275 is currently in Phase I/II clinical trials in recurrent advanced non-small cell lung cancer, combining with 5-azacytidine.
Features
Protocol
Kinase Assay [6]
Standard HDAC Assays Rat liver enzyme is diluted 1:6 with HDAC buffer. Recombinant human HDACs are diluted 1:4 in HDAC buffer. For standard HDAC assays, 60 μL of HDAC buffer is mixed with 10 μL of diluted enzyme solution at 30 °C. The HDAC reaction is started by adding 30 μL substrate solution in HDAC buffer followed by 30 min of incubation at 30 °C. The reaction is stopped by adding 100 μL trypsin solutions (10 mg/ml trypsin in 50 mM Tris-HCl [pH 8.0], 100 mM NaCl, 2 μM TSA). After a 20 min incubation period at 30 °C, the release of AMC is monitored by measuring the fluorescence at 460 nm (λex = 390 nm). Fluorescence intensity is calibrated using free AMC. For standard time course experiments, 20 pmol of substrate is used in the initial 100 μL HDAC reaction. Km and Vmax values are determined by measuring the fluorescence AMC generated by enzymatic cleavage of 2–50 pmol of substrate. The experimental data are analyzed using a Hanes plot. The AMC signals are recorded against a blank with buffer and substrate but without the enzyme.
Cell Assay [2]
Cell Lines A2780, Calu-3, HL-60, K562, St-4, HT-29, KB-3-1, Capan-1, 4-1St and HCT-15 cells
Concentrations ~ 10 μM
Incubation Time 3 days
Methods

Cancer cells (5 × 103) are seeded into each well of 96-well plates and cultured with graded concentrations of MS-275 for 3 days. The cells are stained with 0.1 mg/mL neutral red for 1 hour in a CO2-incubator, and, after aspiration of the medium, OD540 of the neutral red solubilized with 50 μL of ethanol and 150 μL of 0.1 M Na2HPO4 is measured. The IC50 value is determined by plotting growth inhibition of the cells against the logarithm of the drug concentration.

Animal Study [1]
Animal Models A2780, HT-29, HTC-15, KB-3-1, 4-1St, St-4, Capan-1 and Calu-3 cells are injected subcutaneously into the flank of nude mice.
Formulation Dissolved with 0.05 N HCl, 0.1% Tween 80
Doses 12.3, 24.5 and 49 mg/kg
Administration Administered orally once daily 5 days per week for 4 weeks
References
[1] Saito A, et al. Proc Natl Acad Sci U S A, 1999, 96(8), 4592-4597.
[2] Sugawara T, et al. 95th AACR, Orlando, 2004, Abst#2451
[3] Rosato RR, et al. Cancer Res, 2003, 63(13), 3637-3645.
[4] Zhang ZY, et al. Neurosci, 2010, 169, 370-377.
[5] Kato Y, Clin Cancer Res, 2007, 13(15), 4538-4546.
[6] Wegener D, et al. Chem Biol, 2003, 10(1), 61-68.
Toronto Research Chemicals -  E559300 external link
Entinostat is an emerging HDACi (histone deacetylase inhibitor). Entinostat is used for treatment of solid tumors and hematologic malignancies.

参考文献

参考文献

供应商提供 Google Scholar IconGoogle Scholar PubMed iconPubMed Google Books IconGoogle Books
正在搜索,请耐心等待...(如果遇到网页错误或者长时间没有结果,请刷新页面[F5])

专利

专利

PubChem iconPubChem Patent Google Patent Search IconGoogle Patent

互联网资源

互联网资源

百度图标百度 google iconGoogle