[2-(3-Aminomethyl-5-cyclopropyl-[1,2,4]triazol-4-yl)-5-chloro-phenyl]-(2-chloro-phenyl)-methanone | 83520-23-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: [2-(3-Aminomethyl-5-cyclopropyl-[1,2,4]triazol-4-yl)-5-chloro-phenyl]-(2-chloro-phenyl)-methanone
• CAS: 83520-23-4
• 化学式: C₁₉H₁₆Cl₂N₄O
• 分子量: 387.268
• InChiKey: UNGKSEWLRBVQJZ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.14
• 重原子数：
  26.0
• 可旋转键数：
  5.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.21
• 拓扑面积：
  73.8
• 氢给体数：
  1.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  [2-(3-Aminomethyl-5-cyclopropyl-[1,2,4]triazol-4-yl)-5-chloro-phenyl]-(2-chloro-phenyl)-methanone 在 一水合肼 作用下， 以 乙醇 、 N,N-二甲基甲酰胺 、 苯 为溶剂， 反应 2.0h， 生成 2-Amino-N-{4-[4-chloro-2-(2-chloro-benzoyl)-phenyl]-5-cyclopropyl-4H-[1,2,4]triazol-3-ylmethyl}-acetamide
  参考文献：
  名称：

  Amino acid amide derivatives of 2-[3-(aminomethyl)-4H-1,2,4-triazol-4-yl]benzophenones, a novel class of annulated peptidoaminobenzophenones

  摘要：

  A series of the title compounds was prepared via condensation of the 3-(aminomethyl)triazolylbenzophenone (5) with N-protected amino acids, followed by deprotection, amination of the 3-[(chloroacetamido)methyl]triazolylbenzophenone (6a,b), or reduction of the relevant azide derivative (6c). Some of the title compounds were also derived directly from the quinazolines 3 or 4 by acid-induced rearrangement, followed by deprotection. These new amino acid amide derivatives of the triazolylbenzophenones (2) were evaluated for central nervous system (CNS) activity. Members of this class of compounds exhibited a high level of CNS activities. For example, 2',5-dichloro-2-[3-[(glycylamino)methyl]-5-methyl-4H-1,2,4-triazol-4-yl] benzophenone (2c) was as active as triazolam, with an ED50 of 0.58 mg/kg (mice, po), against antifighting activity in the foot shock-induced fighting test. Other triazolylbenzophenone derivatives (2a-f) showed similar pharmacological activities.

  DOI：

  10.1021/jm00354a015
• 作为产物：
  描述：

  乙基(Z)-2-(((苄氧基)羰基)氨基)-N-(4-氯-2-(2-氯苯甲酰基)苯基)乙酰亚胺 在 六甲基磷酰三胺 、 氢溴酸 、 一水合肼 、 溶剂黄146 作用下， 以 乙醇 、 乙腈 为溶剂， 反应 12.0h， 生成 [2-(3-Aminomethyl-5-cyclopropyl-[1,2,4]triazol-4-yl)-5-chloro-phenyl]-(2-chloro-phenyl)-methanone
  参考文献：
  名称：

  Amino acid amide derivatives of 2-[3-(aminomethyl)-4H-1,2,4-triazol-4-yl]benzophenones, a novel class of annulated peptidoaminobenzophenones

  摘要：

  A series of the title compounds was prepared via condensation of the 3-(aminomethyl)triazolylbenzophenone (5) with N-protected amino acids, followed by deprotection, amination of the 3-[(chloroacetamido)methyl]triazolylbenzophenone (6a,b), or reduction of the relevant azide derivative (6c). Some of the title compounds were also derived directly from the quinazolines 3 or 4 by acid-induced rearrangement, followed by deprotection. These new amino acid amide derivatives of the triazolylbenzophenones (2) were evaluated for central nervous system (CNS) activity. Members of this class of compounds exhibited a high level of CNS activities. For example, 2',5-dichloro-2-[3-[(glycylamino)methyl]-5-methyl-4H-1,2,4-triazol-4-yl] benzophenone (2c) was as active as triazolam, with an ED50 of 0.58 mg/kg (mice, po), against antifighting activity in the foot shock-induced fighting test. Other triazolylbenzophenone derivatives (2a-f) showed similar pharmacological activities.

  DOI：

  10.1021/jm00354a015