3-<3-<4-(5-fluoro-1,2-benzisoxazol-3-yl)-1-piperidinyl>propyl>-2-methylindole | 84243-06-1

• 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: 3-<3-<4-(5-fluoro-1,2-benzisoxazol-3-yl)-1-piperidinyl>propyl>-2-methylindole
• 英文别名: 3-{3-[4-(5-fluoro-1,2-benzisoxazol-3-yl)piperidyl]propyl}-2-methylindole；5-fluoro-3-[1-[3-(2-methyl-1H-indol-3-yl)propyl]piperidin-4-yl]-1,2-benzoxazole
• CAS: 84243-06-1
• 化学式: C₂₄H₂₆FN₃O
• 分子量: 391.488
• InChiKey: GCEAGUQGMMAULH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.3
• 重原子数：
  29
• 可旋转键数：
  5
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  45.1
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  1-[4-(5-氟-1,2-苯并异恶唑-3-基)-1-哌啶基]-乙酮 在 盐酸 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 20.0h， 生成 3-<3-<4-(5-fluoro-1,2-benzisoxazol-3-yl)-1-piperidinyl>propyl>-2-methylindole
  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

• STRUPCZEWSKI, J. T.;ALLEN, R. C.;GARDNER, B. A.;SCHMID, B. L.;STACHE, U.;+, J. MED. CHEM., 1985, 28, N 6, 761-769
  作者：STRUPCZEWSKI, J. T.、ALLEN, R. C.、GARDNER, B. A.、SCHMID, B. L.、STACHE, U.、+

  DOI：——

  日期：——
• US4352811A
  申请人：——

  公开号：US4352811A

  公开（公告）日：1982-10-05
• 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).