2-[6-(2-Methyl-[1,3]dioxolan-2-yl)-hexyl]-isoindole-1,3-dione | 85328-48-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 异吲哚及其衍生物
• 英文名称: 2-[6-(2-Methyl-[1,3]dioxolan-2-yl)-hexyl]-isoindole-1,3-dione
• 英文别名: N-[6-(2-Methyl-1,3-dioxolan-2-yl)hexyl]phthalimide；2-[6-(2-methyl-1,3-dioxolan-2-yl)hexyl]isoindole-1,3-dione
• CAS: 85328-48-9
• 化学式: C₁₈H₂₃NO₄
• 分子量: 317.385
• InChiKey: ZTCDCMLNXHCGHC-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  23
• 可旋转键数：
  7
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.56
• 拓扑面积：
  55.8
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  2-[6-(2-Methyl-[1,3]dioxolan-2-yl)-hexyl]-isoindole-1,3-dione 在 光气 、 高氯酸 、 potassium carbonate 、 一水合肼 、 三乙胺 作用下， 以 四氢呋喃 为溶剂， 反应 11.0h， 生成 4-(diphenylmethyl)-1-<<(7-oxooctyl)imino>methyl>piperidine
  参考文献：
  名称：

  Antisecretory activity of human, dog, and rat metabolites of fenoctimine

  摘要：

  Fenoctimine (1a), a nonanticholinergic inhibitor of gastric acid secretion in dogs and rats, was evaluated as a gastric antisecretory agent in humans. In humans it exhibited weak antisecretory activity and caused anticholinergic-like side effects such as dry mouth and nasal passages. Studies of the metabolic fate of fenoctimine in humans, dogs, and rats provided structures of the resultant metabolites. These were synthesized and tested for antisecretory and anticholinergic activity. The human metabolites were all less active than fenoctimine as antisecretory agents, and some displayed significant anticholinergic activity. These results suggest that the unexpectedly weak effect of fenoctimine as a gastric antisecretory agent in humans, as well as anticholinergic effects, may be due to its extensive metabolism, which is different from that seen in dog and rat.

  DOI：

  10.1021/jm00388a025
• 作为产物：
  描述：

  N-(5-溴戊基)邻苯二甲酰亚胺 在 盐酸 、 sodium ethanolate 、 对甲苯磺酸 、 溶剂黄146 作用下， 以 乙醇 、 水 、 苯 为溶剂， 反应 6.5h， 生成 2-[6-(2-Methyl-[1,3]dioxolan-2-yl)-hexyl]-isoindole-1,3-dione
  参考文献：
  名称：

  Antisecretory activity of human, dog, and rat metabolites of fenoctimine

  摘要：

  Fenoctimine (1a), a nonanticholinergic inhibitor of gastric acid secretion in dogs and rats, was evaluated as a gastric antisecretory agent in humans. In humans it exhibited weak antisecretory activity and caused anticholinergic-like side effects such as dry mouth and nasal passages. Studies of the metabolic fate of fenoctimine in humans, dogs, and rats provided structures of the resultant metabolites. These were synthesized and tested for antisecretory and anticholinergic activity. The human metabolites were all less active than fenoctimine as antisecretory agents, and some displayed significant anticholinergic activity. These results suggest that the unexpectedly weak effect of fenoctimine as a gastric antisecretory agent in humans, as well as anticholinergic effects, may be due to its extensive metabolism, which is different from that seen in dog and rat.

  DOI：

  10.1021/jm00388a025

文献信息

• Antisecretory 4-diphenylmethyl-1-[(oxoalkyl)imino]methyl-piperidines and
  申请人：McNeilab, Inc.

  公开号：US04370335A1

  公开（公告）日：1983-01-25

  4-Diphenyl-1-[(oxo and oxo-related alkyl)imino]methyl-piperidine derivatives are disclosed which are useful for the inhibition of gastric acid secretion.

  本文披露了4-二苯基-1-[(氧化和氧化相关烷基)亚胺基]甲基-哌啶衍生物，其可用于抑制胃酸分泌。
• 4-Diphenylmethyl-1-(oxoalkyl)imino)methyl-piperidines and their derivatives
  申请人：McNeilab, Inc.

  公开号：EP0087853A2

  公开（公告）日：1983-09-07

  4-diphenyl-1-[(oxo and oxo-related alkyl)imino]methylpiperidine derivatives are disclosed which are useful for the inhibition of gastric acid secretion.

  本研究公开了可用于抑制胃酸分泌的 4-二苯基-1-[（氧代和氧代相关烷基）亚氨基]甲基哌啶衍生物。
• US4370335A
  申请人：——

  公开号：US4370335A

  公开（公告）日：1983-01-25
• Antisecretory activity of human, dog, and rat metabolites of fenoctimine
  作者：Malcolm K. Scott、Henry I. Jacoby、Antoinette C. Bonfilio、Thomas W. Corcoran、Iris S. Lopez

  DOI：10.1021/jm00388a025

  日期：1987.5

  Fenoctimine (1a), a nonanticholinergic inhibitor of gastric acid secretion in dogs and rats, was evaluated as a gastric antisecretory agent in humans. In humans it exhibited weak antisecretory activity and caused anticholinergic-like side effects such as dry mouth and nasal passages. Studies of the metabolic fate of fenoctimine in humans, dogs, and rats provided structures of the resultant metabolites. These were synthesized and tested for antisecretory and anticholinergic activity. The human metabolites were all less active than fenoctimine as antisecretory agents, and some displayed significant anticholinergic activity. These results suggest that the unexpectedly weak effect of fenoctimine as a gastric antisecretory agent in humans, as well as anticholinergic effects, may be due to its extensive metabolism, which is different from that seen in dog and rat.