N'-(2-(1,3-dioxoisoindolin-2-yl)acetoxy)-4-methylbenzimidamide | 892006-05-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吲哚及其衍生物
• 英文名称: N'-(2-(1,3-dioxoisoindolin-2-yl)acetoxy)-4-methylbenzimidamide
• CAS: 892006-05-2
• 化学式: C₁₈H₁₅N₃O₄
• 分子量: 337.335
• InChiKey: SUALJGGBOYOQKF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.45
• 重原子数：
  25.0
• 可旋转键数：
  4.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.11
• 拓扑面积：
  102.06
• 氢给体数：
  1.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  N'-(2-(1,3-dioxoisoindolin-2-yl)acetoxy)-4-methylbenzimidamide 以 乙二醇二甲醚 为溶剂， 反应 16.0h， 生成 N-[3-(p-tolyl)-1,2,4-oxadiazol-5-yl-methyl]phthalimide
  参考文献：
  名称：

  Synthesis, characterization and interaction mechanism of new oxadiazolo-phthalimides as peripheral analgesics. IV

  摘要：

  The synthesis, characterization and spectroscopic studies of compounds 6a-g with analgesic activity is described. A new model of interaction between the drug and the enzyme is suggested. Application of the Resonance Valence Bond theory led us to propose. for the first time, an entirely new mechanism involving an electron transfer from the amino acid residue of the enzyme to the drug. Theoretical studies of various transition states involved in the interaction mechanism employing the semi-empirical molecular orbital calculations (AMI method) have been carried out. This article also deals with an extensive study of the structure-activity relationships of seven oxadiazolo-phthalimides 6a-g. (C) 2003 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/s0022-2860(03)00418-6
• 作为产物：
  描述：

  邻苯二甲酰甘氨酸 、 4-甲基苯甲酰胺肟 在 N,N'-二环己基碳二亚胺 作用下， 以 乙二醇二甲醚 为溶剂， 反应 30.0h， 生成 N'-(2-(1,3-dioxoisoindolin-2-yl)acetoxy)-4-methylbenzimidamide
  参考文献：
  名称：

  Synthesis, characterization and interaction mechanism of new oxadiazolo-phthalimides as peripheral analgesics. IV

  摘要：

  The synthesis, characterization and spectroscopic studies of compounds 6a-g with analgesic activity is described. A new model of interaction between the drug and the enzyme is suggested. Application of the Resonance Valence Bond theory led us to propose. for the first time, an entirely new mechanism involving an electron transfer from the amino acid residue of the enzyme to the drug. Theoretical studies of various transition states involved in the interaction mechanism employing the semi-empirical molecular orbital calculations (AMI method) have been carried out. This article also deals with an extensive study of the structure-activity relationships of seven oxadiazolo-phthalimides 6a-g. (C) 2003 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/s0022-2860(03)00418-6

文献信息

• New phthalimide derivatives with potent analgesic activity: II
  作者：Roberto Antunes、Hildson Batista、R.M. Srivastava、G. Thomas、C.C. Araujo

  DOI：10.1016/s0960-894x(98)00558-7

  日期：1998.11

  Seven new phthalimide derivatives (9a-g) with 1,2,4-oxadiazol-5-yl methyl group attached to nitrogen have been synthesized from N-phthaloylglycine 6 and arylamidoximes 7a-g. All of these showed potent analgesic effect with acetic acid induced "writhing" test in mice. One of the better compounds (ID50 = 2.2 mg/Kg i.p.) has been found to be 9a which also demonstrates analgesic activity against inflammatory

  由N-邻苯二甲酰基甘氨酸6和芳酰胺基肟7a-g合成了七个新的具有与氮相连的1,2,4-恶二唑-5-基甲基的邻苯二甲酰亚胺衍生物（9a-g）。所有这些都显示了乙酸引起的小鼠“扭体”试验的有效镇痛作用。发现更好的化合物之一（ID50 = 2.2 mg / Kg ip）为9a，它也显示出抗炎性疼痛的镇痛活性。