N-(1-hydroxy-1-phenylpropan-2-yl)-N,2,2,3,3-pentamethylcyclopropane-1-carboxamide | 1043455-55-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: N-(1-hydroxy-1-phenylpropan-2-yl)-N,2,2,3,3-pentamethylcyclopropane-1-carboxamide
• CAS: 1043455-55-5
• 化学式: C₁₈H₂₇NO₂
• 分子量: 289.418
• InChiKey: GKGDGKWBRPGVHU-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  21
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.61
• 拓扑面积：
  40.5
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  2,2,3,3-四甲基环丙烷羧酸酰氯 、 2-(甲基氨基)-1-苯基-1-丙醇 在 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 3.0h， 以89%的产率得到N-(1-hydroxy-1-phenylpropan-2-yl)-N,2,2,3,3-pentamethylcyclopropane-1-carboxamide
  参考文献：
  名称：

  Synthesis and anticonvulsant activity of aromatic tetramethylcyclopropanecarboxamide derivatives

  摘要：

  As part of our ongoing research on potential new antiepileptic drugs (AEDs), a series of tetramethylcyclopropanecarboxamide derivatives containing benzene ring were designed, synthesized, and evaluated for anticonvulsant activities in the murine maximal electroshock (MES) and subcutaneous pentylenetetrazole (scMet) seizure tests. The most potent compound emerging from this study was N-(2,2,3,3-tetramethylcyclopropanecarboxamide)-p-phenyl-sulfonamide (21), possessing an ED50 value of 26 mg/kg in the rat-MES test and a remarkable PI (PI = TD50/ED50) value above 19. The better anticonvulsant potency of compound 21 and its wider safety margin compared to valproic acid (VPA) and zonisamide make it a potential candidate to become a new AED second-generation to VPA. (C) 2008 Published by Elsevier Ltd.

  DOI：

  10.1016/j.bmc.2008.03.051

文献信息

• Synthesis and anticonvulsant activity of aromatic tetramethylcyclopropanecarboxamide derivatives
  作者：Jakob Avi Shimshoni、Meir Bialer、Boris Yagen

  DOI：10.1016/j.bmc.2008.03.051

  日期：2008.6

  As part of our ongoing research on potential new antiepileptic drugs (AEDs), a series of tetramethylcyclopropanecarboxamide derivatives containing benzene ring were designed, synthesized, and evaluated for anticonvulsant activities in the murine maximal electroshock (MES) and subcutaneous pentylenetetrazole (scMet) seizure tests. The most potent compound emerging from this study was N-(2,2,3,3-tetramethylcyclopropanecarboxamide)-p-phenyl-sulfonamide (21), possessing an ED50 value of 26 mg/kg in the rat-MES test and a remarkable PI (PI = TD50/ED50) value above 19. The better anticonvulsant potency of compound 21 and its wider safety margin compared to valproic acid (VPA) and zonisamide make it a potential candidate to become a new AED second-generation to VPA. (C) 2008 Published by Elsevier Ltd.