2-(5-methyl-2,3-dioxoindolin-1-yl)-N-phenylacetamide | 1020957-54-3

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: 2-(5-methyl-2,3-dioxoindolin-1-yl)-N-phenylacetamide
• 英文别名: 2-(5-methyl-2,3-dioxoindol-1-yl)-N-phenylacetamide
• CAS: 1020957-54-3
• 化学式: C₁₇H₁₄N₂O₃
• 分子量: 294.31
• InChiKey: KNLPCPORAUZNEM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  22
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  66.5
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  2-hydroxyimino-N-p-tolyl-acetamide 在 硫酸 、 potassium carbonate 作用下， 以 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 1.0h， 生成 2-(5-methyl-2,3-dioxoindolin-1-yl)-N-phenylacetamide
  参考文献：
  名称：

  Structure-based design, synthesis, and anticonvulsant activity of isatin-1-N-phenylacetamide derivatives

  摘要：

  In an effort to develop the potent anticonvulsant agents, a series of novel isatin-1-N-phenylacetamide derivatives was synthesized and screened for their in vivo anticonvulsant activity against maximal electroshock test and evaluated for their neurotoxicity by the rotarod test at the same dose levels. Ten compounds exhibited the anticonvulsant activity. 2-(5-Methyl-2,3-dioxoindolin-1-yl)-N-phenylacetamide (4b) was found to be the most potent compound of the series with an ED50 of 91.3 mg/kg, TD50 of > 1,000 mg/kg, a higher protective index (PI = TD50/ED50, > 11) was gained than the reference drug phenobarbital and carbamazepine. The essential structural features responsible for interaction with receptor site are established within a suggested pharmacophore.

  DOI：

  10.1007/s00044-013-0811-1

文献信息

• Shp-2 Inhibitors, Pharmaceutical Compositons Comprising Them and Their Use For Treating Phosphatase-Mediated Diseases
  申请人：Hellmuth Klaus

  公开号：US20080194563A1

  公开（公告）日：2008-08-14

  The present invention relates to small molecule protein tyrosine phosphatase inhibitors, especially Shp-2 inhibitors, of formula (I) and/or (II), and to pharmaceutical compositions comprising them. The invention is also directed to the use of said compounds for the treatment of phosphatase-mediated diseases, especially cancer and metastasis. The invention further concerns a method for treating a proliferative disease, a genetic disorder, an autoimmune disease, an angiogenic disorder or cancer in a patient in need of such treatment, comprising administering to said patient a therapeutically effective amount of at least one compound of formula (I) and/or (II).

  本发明涉及小分子蛋白酪氨酸磷酸酶抑制剂，特别是Shp-2抑制剂，其化学式为(I)和/或(II)，以及包含它们的制药组合物。该发明还涉及使用所述化合物治疗磷酸酶介导的疾病，特别是癌症和转移。本发明还涉及一种治疗增殖性疾病、遗传性疾病、自身免疫性疾病、血管生成障碍或癌症的方法，包括向该患者施用至少一种化合物(I)和/或(II)的治疗有效量。
• US7868185B2
  申请人：——

  公开号：US7868185B2

  公开（公告）日：2011-01-11
• Structure-based design, synthesis, and anticonvulsant activity of isatin-1-N-phenylacetamide derivatives
  作者：Chao Xie、Li-Ming Tang、Fu-Nan Li、Li-Ping Guan、Cheng-Yan Pan、Si-Hong Wang

  DOI：10.1007/s00044-013-0811-1

  日期：2014.5

  In an effort to develop the potent anticonvulsant agents, a series of novel isatin-1-N-phenylacetamide derivatives was synthesized and screened for their in vivo anticonvulsant activity against maximal electroshock test and evaluated for their neurotoxicity by the rotarod test at the same dose levels. Ten compounds exhibited the anticonvulsant activity. 2-(5-Methyl-2,3-dioxoindolin-1-yl)-N-phenylacetamide (4b) was found to be the most potent compound of the series with an ED50 of 91.3 mg/kg, TD50 of > 1,000 mg/kg, a higher protective index (PI = TD50/ED50, > 11) was gained than the reference drug phenobarbital and carbamazepine. The essential structural features responsible for interaction with receptor site are established within a suggested pharmacophore.