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186392-40-5 分子结构
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(2R,3S)-3-[(5-chloro-1H-indol-2-yl)formamido]-2-hydroxy-N,N-dimethyl-4-phenylbutanamide

ChemBase编号:73187
分子式:C21H22ClN3O3
平均质量:399.87068
单一同位素质量:399.13496926
SMILES和InChIs

SMILES:
c1(ccc2c(c1)cc([nH]2)C(=O)N[C@H]([C@H](C(=O)N(C)C)O)Cc1ccccc1)Cl
Canonical SMILES:
Clc1ccc2c(c1)cc([nH]2)C(=O)N[C@H]([C@H](C(=O)N(C)C)O)Cc1ccccc1
InChI:
InChI=1S/C21H22ClN3O3/c1-25(2)21(28)19(26)17(10-13-6-4-3-5-7-13)24-20(27)18-12-14-11-15(22)8-9-16(14)23-18/h3-9,11-12,17,19,23,26H,10H2,1-2H3,(H,24,27)/t17-,19+/m0/s1
InChIKey:
HINJNZFCMLSBCI-PKOBYXMFSA-N

引用这个纪录

CBID:73187 http://www.chembase.cn/molecule-73187.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
(2R,3S)-3-[(5-chloro-1H-indol-2-yl)formamido]-2-hydroxy-N,N-dimethyl-4-phenylbutanamide
IUPAC传统名
(2R,3S)-3-[(5-chloro-1H-indol-2-yl)formamido]-2-hydroxy-N,N-dimethyl-4-phenylbutanamide
别名
CP-91149
2-Methyl-2-[3-[(3S)-1-[[4-(1-methylethyl)phenyl]acetyl]-3-piperidinyl]phenoxy]propanoic Acid
CP 775146
(S)-2-[3-[1-[(4-Isopropylphenyl)acetyl]piperidin-3-yl]phenoxy]-2-methylpropionic Acid
PF-06340672
CP-775146
5-Chloro-N-[(1S,2R)-3-(dimethylamino)-2-hydroxy-3-oxo-1-(phenylmethyl)propyl]-1H-indole-2-carboxamide
CP-91149
CAS号
186392-40-5
702680-17-9
MDL号
MFCD00954145
PubChem SID
162038107
PubChem CID
9843900

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 9843900 external link

理论计算性质

理论计算性质

JChem
Acid pKa 12.074857  质子受体
质子供体 LogD (pH = 5.5) 2.3835182 
LogD (pH = 7.4) 2.38351  Log P 2.3835185 
摩尔折射率 108.5775 cm3 极化性 42.705753 Å3
极化表面积 85.43 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 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
Methanol expand 查看数据来源
外观
Off-White Solid expand 查看数据来源
white to off-white powder expand 查看数据来源
熔点
70-76°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
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
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
危险公开号
22 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
H302 expand 查看数据来源
保存温度
2-8°C 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)
C21H22ClN3O3 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 -  S2717 external link
Research Area
Description Cancer
Biological Activity
Description CP-91149 is a selective glycogen phosphorylase (GP) inhibitor with IC50 of 0.13 μM.
Targets GP
IC50 0.13 μM [1]
In Vitro CP-91149 displays 200-fold higher inhibitory activity against human liver glycogen phosphorylase a (HLGPa) than caffeine (IC50 = 26 μM). CP-91149 (10-100 μM) inhibits glucagon-stimulated glycogenolysis in isolated rat hepatocytes in a dose-dependent manner, and in primary human hepatocytes with IC50 of ~2.1 μM. [1] CP-91149 also potently inhibits the activities of human muscle phosphorylase a and b with IC50 of 0.2 μM and ~0.3 μM, respectively. CP-91149 treatment at 2.5 μM induces inactivation of phosphorylase and sequential activation of glycogen synthase in hepatocytes, and increases glycogen synthesis by 7-fold at 5 mM glucose and by 2-fold at 20 mM glucose. CP-91149 can partially counteract the effects of phosphorylase overexpression. [2] CP-91149 also potently inhibits brain GP with IC50 of 0.5 μM in A549 cells. CP-91149 treatment at 10-30 μM causes significant glycogen accumulation in A549 and HSF55 cells. CP-91149 treatment increases G1-phase cells with a significant reduction of the S-phase population in HSF55 cells, correlated with increased expression of p21 and p27. [3] CP-91149 also promotes the dephosphorylation and activation of GS (glycogen synthase) in non-engineered or GP-overexpressing cultured human muscle cells, but exclusively in glucose-deprived cells. [4]
In Vivo Oral administration of CP-91149 to diabetic ob/ob mice at 25-50 mg/kg causes rapid (3 hours) glucose lowering by 100-120 mg/dl without producing hypoglycemia, resulting from inhibition of glycogenolysis in vivo. CP-91149 treatment does not lower glucose levels in normoglycemic, nondiabetic mice. [1] In the non-fasted Goto-Kakizaki (GK) rats, administration of CP-91149 in combination with CS-917 suppresses hepatic glycogen reduction by CS-917 and decreases plasma glucose more than single administration of CS-917. [5]
Clinical Trials
Features
Combination Therapy
Description HLGPa inhibition by CP-91149 is synergistic with caffeine and theophylline, as caffeine or theophylline increases the potency (IC50) of CP-91149 from 1 μM to 0.14 μM. [1]
Protocol
Kinase Assay [1]
Phosphorylase enzyme assay Human liver glycogen phosphorylase a (HLGPa, 85 ng) activity is measured in the direction of glycogen synthesis by the release of phosphate from glucose-1-phosphate at 22°C in 100 μL of buffer containing 50 mM Hepes (pH 7.2), 100 mM KCl, 2.5 mM EGTA, 2.5 mM MgCl2, 0.5 mM glucose-1-phosphate, and 1 mg/mL glycogen. Phosphate is measured at 620 nm, 20 minutes after the addition of 150 μL of 1 M HCl containing 10 mg/mL ammonium molybdate and 0.38 mg/mL malachite green. Increasing concentrations of CP-91149 are added to the assay in 5 μL of 14% DMSO.
Cell Assay [3]
Cell Lines HSF55 and T98G
Concentrations Dissolved in DMSO, final concentrations ~50 μM
Incubation Time 72 hours
Methods Cells are exposed to various concentrations of CP-91149 for 72hours. Viability is determined with manual cell counts following staining with trypan blue exclusion assay. Cells are fixed with 70% ethanol. DNA is stained with propidium iodide and the intensity of fluorescence is measured using a Becton-Dickinson flow cytometer at 488nm for excitation and at 650nm for emission. The cell cycle profile is analyzed using Modifit’s Sync Wizard.
Animal Study [1]
Animal Models Obese, diabetic male C57BL/6J-Lep(ob/ob) mice and their lean, nondiabetic C57BL/6J-?/+ littermates
Formulation Formulated in vehicle consisting of either 0.25% (wt/vol) methyl cellulose in water or 0.1% Pluronic P105 Block Copolymer Surfactant in 0.1% saline
Doses ~50 mg/kg
Administration Orally
References
[1] Martin WH, et al. Proc Natl Acad Sci U S A, 1998, 95(4), 1776-1781.
[2] Aiston S, et al. J Biol Chem, 2001, 276(26), 23858-23866.
[3] Schnier JB, et al. Biochem Biophys Res Commun, 2003, 309(1), 126-134.
[4] Lerín C, et al. Biochem J, 2004, 378(Pt 3), 1073-1077.
[5] Yoshida T, et al. J Pharmacol Sci, 2011, 115(3), 329-335.
Sigma Aldrich -  PZ0104 external link
Biochem/physiol Actions
CP-91149 is a selective glycogen phosphorylase inhibitor.
Legal Information
Sold for research purposes under agreement from Pfizer Inc.
Toronto Research Chemicals -  C781355 external link
A potent and selective PPARα agonist. It exhibits hypolipidemic activity in vivo.

参考文献

参考文献

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