3-[3-[4-(6-Chloro-1,2-benzoxazol-3-yl)piperidin-1-yl]propyl]-6-fluoro-1,2-benzoxazole | 84243-11-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并异恶唑
• 英文名称: 3-[3-[4-(6-Chloro-1,2-benzoxazol-3-yl)piperidin-1-yl]propyl]-6-fluoro-1,2-benzoxazole
• CAS: 84243-11-8
• 化学式: C₂₂H₂₁ClFN₃O₂
• 分子量: 413.879
• InChiKey: DXPMTMYUYCIASC-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.2
• 重原子数：
  29
• 可旋转键数：
  5
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  55.3
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  1-Formyl-4-(2,4-dichlorobenzoyl)piperidine oxime 在 盐酸 、 sodium hydride 、 potassium carbonate 、 potassium iodide 作用下， 以 乙醇 、 N,N-二甲基甲酰胺 为溶剂， 反应 12.0h， 生成 3-[3-[4-(6-Chloro-1,2-benzoxazol-3-yl)piperidin-1-yl]propyl]-6-fluoro-1,2-benzoxazole
  参考文献：
  名称：

  Synthesis and neuroleptic activity of 3-(1-substituted-4-piperidinyl)-1,2-benzisoxazoles

  摘要：

  The synthesis of a series of 3-(1-substituted-4-piperidinyl)-1,2-benzisoxazoles is described. The neuroleptic activity of the series was evaluated by utilizing the climbing mice assay and inhibition of [3H]spiroperidol binding. Structure-activity relationships were studied by variation of the substituent on the benzisoxazole ring with concomitant variation of four different 1-piperidinyl substituents. Maximum neuroleptic activity was realized when there was a 6-fluoro substituent on the benzisoxazole ring. The 1-piperidinyl substituent appeared less significant, although in most cases, the (1,3-dihydro-2-oxo-2H-benzimidazol-1-yl)propyl group imparted maximum potency. The most potent compound in both assays was 6-fluoro-3-[1-[3-(1,3-dihydro-2-oxo-2H-benzimidazol-1-yl) propyl]-4-piperidinyl]-1,2-benzisoxazole (11b).

  DOI：

  10.1021/jm00383a012

文献信息

• Synthesis and neuroleptic activity of 3-(1-substituted-4-piperidinyl)-1,2-benzisoxazoles
  作者：Joseph T. Strupczewski、Richard C. Allen、Beth Ann Gardner、Blaine L. Schmid、Ulrich Stache、Edward J. Glamkowski、Michael C. Jones、Daniel B. Ellis、Francis P. Huger、Robert W. Dunn

  DOI：10.1021/jm00383a012

  日期：1985.6

  The synthesis of a series of 3-(1-substituted-4-piperidinyl)-1,2-benzisoxazoles is described. The neuroleptic activity of the series was evaluated by utilizing the climbing mice assay and inhibition of [3H]spiroperidol binding. Structure-activity relationships were studied by variation of the substituent on the benzisoxazole ring with concomitant variation of four different 1-piperidinyl substituents. Maximum neuroleptic activity was realized when there was a 6-fluoro substituent on the benzisoxazole ring. The 1-piperidinyl substituent appeared less significant, although in most cases, the (1,3-dihydro-2-oxo-2H-benzimidazol-1-yl)propyl group imparted maximum potency. The most potent compound in both assays was 6-fluoro-3-[1-[3-(1,3-dihydro-2-oxo-2H-benzimidazol-1-yl) propyl]-4-piperidinyl]-1,2-benzisoxazole (11b).