恩他卡朋杂质10 | 158693-01-7

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 肉桂酸及其衍生物
• 中文名称: 恩他卡朋杂质10
• 英文名称: (E)-2-cyano-3-(3,4-dihydroxy-5-nitrophenyl)acrylamide
• 英文别名: Entacapone amide；(E)-2-cyano-3-(3,4-dihydroxy-5-nitrophenyl)prop-2-enamide
• CAS: 158693-01-7
• 化学式: C₁₀H₇N₃O₅
• 分子量: 249.183
• InChiKey: IZXCSWDOAKESAA-LZCJLJQNSA-N

物化性质

• 熔点：
  300-303 °C(Solv: ethanol (64-17-5))
• 沸点：
  550.3±50.0 °C(Predicted)
• 密度：
  1.665±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.4
• 重原子数：
  18
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  153
• 氢给体数：
  3
• 氢受体数：
  6

安全信息

• 危险性防范说明：
  P261,P264,P270,P271,P280,P301+P312,P302+P352,P304+P340,P305+P351+P338,P330,P332+P313,P337+P313,P362,P403+P233,P405,P501
• 危险性描述：
  H302,H315,H319,H335

反应信息

• 作为产物：
  描述：

  香草醛 在 N-甲基哌嗪 、 氢溴酸 、 硝酸 、 溶剂黄146 作用下， 以 甲醇 、 水 为溶剂， 反应 24.0h， 生成 恩他卡朋杂质10
  参考文献：
  名称：

  Arylcyanoacrylamides as inhibitors of the Dengue and West Nile virus proteases

  摘要：

  The 3-aryl-2-cyanoacrylamide scaffold was designed as core pharmacophore for inhibitors of the Dengue and West Nile virus serine proteases (NS2B-NS3). A total of 86 analogs was prepared to study the structure-activity relationships in detail. Thereby, it turned out that the electron density of the aryl moiety and the central double bond have a crucial influence on the activity of the compounds, whereas the influence of substituents of the amide residue is less relevant. The para-hydroxy substituted analog was found to be the most potent inhibitor in this series with a K(i)-value of 35.7 mu M at the Dengue and 44.6 mu M at the West Nile virus protease. The aprotinin competition assay demonstrates a direct interaction of the inhibitor molecule with active centre of the Dengue virus protease. The target selectivity was studied in a counterscreen with thrombin and found to be 2.8:1 in favor of DEN protease and 2.3:1 in favor of WNV protease, respectively. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2011.10.061

文献信息

• Stable polymorphs of (E)-N,N-diethyl-2-cyano-3-(3,4-dihydroxy-5-nitrophenyl)acrylamide
  申请人：Jaweed Mukarram Siddiqui Mohammed

  公开号：US20080004343A1

  公开（公告）日：2008-01-03

  The present invention provides stable crystalline polymorphic Form C and Form D of (E)-Entacapone, (E)-N,N-diethyl-2-cyano-3-(3,4-dihydroxy-5-henyl)acrylamide and processes for their preparation. The polymorphic Form C and Form D of (E)-Entacapone are characterized by specific Infra Red (IR) and X-ray powder diffraction peak values.

  本发明提供了(E)-恩他卡朋的稳定结晶多形体C和多形体D，以及它们的制备方法。 (E)-恩他卡朋的多形体C和多形体D具有特定的红外(IR)和X射线粉末衍射峰值。
• The synthesis and biological evaluation of some caffeic acid amide derivatives: E-2-Cyano-(3-substituted phenyl)acrylamides
  作者：Wei Zhou、Hai-bo Li、Chun-nian Xia、Xian-ming Zheng、Wei-xiao Hu

  DOI：10.1016/j.bmcl.2009.02.081

  日期：2009.4

  A series of caffeic acid amide derivatives 2-cyano-(3-substituted phenyl)acrylamides were synthesized via Knoevenogal condensation of substituted benzaldehydes with cyanoacetamides. The structure of compound 1f was determined as E-isomer by X-ray diffractive analysis. The biological screening tests in vitro showed that compound 1b has obvious inhibitory activities against human gastric carcinoma cell

  通过取代苯甲醛与氰基乙酰胺的Knoevenogal缩合反应，合成了一系列咖啡酸酰胺衍生物2-氰基-（3-取代的苯基）丙烯酰胺。通过X射线衍射分析确定化合物1f的结构为E-异构体。体外生物筛选试验表明，化合物1b对人胃癌细胞系BGC-823，人鼻咽癌细胞系KB和人肝癌细胞系BEL-7402具有明显的抑制活性，IC 50值为5.6μg/ mL，13.1μg。 / mL和12.5μg/ mL。还提出了一些初步的构效关系（SAR），这可能为进一步研究提供指导。
• COMPOSITIONS AND METHODS FOR THE TREATMENT OF PARKINSON'S DISEASE
  申请人：Kandula Mahesh

  公开号：US20150126591A1

  公开（公告）日：2015-05-07

  The invention relates to the compounds of formula I or its pharmaceutical acceptable salts, as well as polymorphs, solvates, enantiomers, stereoisomers and hydrates thereof. The pharmaceutical compositions comprising an effective amount of compounds of formula I, and methods for the treatment of Parkinson's disease may be formulated for oral, buccal, rectal, topical, transdermal, transmucosal, intravenous, parenteral administration, syrup, or injection. Such compositions may be also used for the treatment of Huntington's disease, Alzheimer's disease, Multiple Sclerosis, Lateral Sclerosis, Neural Motor disorders.

  本发明涉及公式I化合物或其药学可接受的盐，以及其多晶形、溶剂合物、对映体、立体异构体和水合物。含有公式I化合物的有效量的药物组合物，以及用于帕金森病的治疗方法，可以制成口服、颊下、直肠、局部、经皮、经黏膜、静脉、肌肉注射、糖浆或注射剂。这样的组合物也可用于治疗亨廷顿病、阿尔茨海默病、多发性硬化症、侧索硬化症、神经运动障碍。
• Stabile polymorphic form of (E)-N,N-diethyl-2-cyano-3-(3,4-dihydroxy-5-nitrophenyl) acrylamide and the process for its preparation
  申请人：ORION-YHTYMÄ OY

  公开号：EP0426468A2

  公开（公告）日：1991-05-08

  Stable and crystallographically essentially pure polymorphic form A of (E)-N,N-diethyl-2-cyano-3-(3,4-dihydroxy-­5-nitro-phenyl)acrylamide may be prepared by crystallizing crude synthesis product from lower aliphatic carboxylic acid such as formic or acetic acid with a catalytic amount of hydrochloric or hydrobromic acid added. The product is a potent inhibitor of catechol-O-methyl-transferase enzyme (COMT).

  通过将低级脂肪族羧酸（如甲酸或乙酸）的粗合成产物结晶，并加入催化量的盐酸或氢溴酸，可制备出稳定的、结晶学上基本纯的多晶型 A (E)-N,N-二乙基-2-氰基-3-(3,4-二羟基-5-硝基苯基)丙烯酰胺。该产品是儿茶酚-O-甲基转移酶（COMT）的强效抑制剂。
• Catechol derivatives, their physiologically acceptable salts, esters and their use in the treatment of tissue damage induced by lipid peroxidation
  申请人：ORION-YHTYMÄ OY

  公开号：EP0444899A2

  公开（公告）日：1991-09-04

  Known and new catechol derivatives may be used as medicinal antioxidants in the prevention or treatment of tissue damage induced by lipid peroxidation. The conditions and diseases which may be treated are for example heart diseases, rheumatoid arthritis, cancer, inflammatory diseases, a rejection reaction in organ transplants, ischemia, cancer and aging.

  已知的和新的儿茶酚衍生物可用作药用抗氧化剂，用于预防或治疗脂质过氧化引起的组织损伤。可治疗的病症和疾病包括心脏病、风湿性关节炎、癌症、炎症性疾病、器官移植中的排异反应、缺血、癌症和衰老等。