5-bromo-1,2,3,3a,8,8a-hexahydro-1,3a,8-trimethylpyrrolo[2,3-b]indole | 138590-85-9

• 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: 5-bromo-1,2,3,3a,8,8a-hexahydro-1,3a,8-trimethylpyrrolo[2,3-b]indole
• 英文别名: 7-bromo-3,4,8b-trimethyl-2,3a-dihydro-1H-pyrrolo[2,3-b]indole
• CAS: 138590-85-9
• 化学式: C₁₃H₁₇BrN₂
• 分子量: 281.195
• InChiKey: PJFSATAJQZIYRT-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  16
• 可旋转键数：
  0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.54
• 拓扑面积：
  6.5
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  5-bromo-1,2,3,3a,8,8a-hexahydro-1,3a,8-trimethylpyrrolo[2,3-b]indole 、 sodium methylate 在 copper(l) iodide 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 2.0h， 生成 (+/-)-esermethole
  参考文献：
  名称：

  一种新颖高效的全合成（±）-毒扁豆碱

  摘要：

  Wittig烯烃化-Claisen重排方案在全合成（±）-毒扁豆碱中的应用。

  DOI：

  10.1016/j.tetlet.2009.03.012
• 作为产物：
  描述：

  1,3a,8-trimethyl-1,2,3,3a,8,8a-hexahydropyrrolo[2,3-b]indole 在 N-溴代丁二酰亚胺(NBS) 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 2.0h， 生成 5-bromo-1,2,3,3a,8,8a-hexahydro-1,3a,8-trimethylpyrrolo[2,3-b]indole
  参考文献：
  名称：

  一种新颖高效的全合成（±）-毒扁豆碱

  摘要：

  Wittig烯烃化-Claisen重排方案在全合成（±）-毒扁豆碱中的应用。

  DOI：

  10.1016/j.tetlet.2009.03.012

文献信息

• Alpha-oxopyrrolo[2,3-B]indole acetic acids, esters, amides and related
  申请人：Hoechst-Roussel Pharmaceuticals Incorporated

  公开号：US05173497A1

  公开（公告）日：1992-12-22

  This invention relates to compounds of the formula ##STR1## where X is --NH, oxygen, N-loweralkyl, or N-arylloweralkyl; R.sub.1 is hydrogen, loweralkyl, cycloalkyl, aryl, arylloweralkyl, loweralkylene, haloloweralkyl, heteroaryl selected from the group consisting of thienyl, furnayl, pyrrolyl and pyridinyl; heteroarylloweralkyl, heterocyclic selected from piperidinyl, piperazinyl, pyrrolidinyl; or heterocyclicloweralkyl; R.sub.2 is hydrogen or loweralkyl; R.sub.3 is loweralkyl or arylloweralkyl; R.sub.4 is hydrogen, loweralkyl, loweralkenyl, loweralkynyl, arylloweralkyl, formyl, loweralkylcarbonyl, arylloweralkylcarbonyl or loweralkoxycarbonyl; Y is hydrogen, loweralkyl or loweralkoxy, and the pharmaceutically acceptable acid addition salts thereof, and where applicable, the geometric and optical isomers and racemic mixtures thereof. The compounds of this invention are useful in the treatment of memory impairment characterized by a cholinergic deficit such as that associated with electroshock-induced amnesia and Alzheimer's disease and other senile dementia.

  这项发明涉及以下结构的化合物：其中X为--NH、氧、N-较低烷基或N-芳基较低烷基；R.sub.1为氢、较低烷基、环烷基、芳基、芳基较低烷基、较低烷基亚烯烃、卤代较低烷基、噻吩基、呋喃基、吡咯基和吡啶基所选的杂环芳基较低烷基、哌啶基、哌嗪基、吡咯基所选的杂环基和杂环较低烷基；R.sub.2为氢或较低烷基；R.sub.3为较低烷基或芳基较低烷基；R.sub.4为氢、较低烷基、较低烯烃基、较低炔烃基、芳基较低烷基、甲酰基、较低烷基羰基、芳基较低烷基羰基或较低烷氧羰基；Y为氢、较低烷基或较低烷氧基，以及其药用可接受的酸盐，必要时包括其几何和光学异构体和消旋混合物。本发明的化合物在治疗由胆碱缺乏引起的记忆障碍方面具有用途，例如与电击诱发的遗忘症和老年痴呆症等相关的情况。
• Pyrrolo[2,3-b]indole-ketones and analogs
  申请人：Hoechst-Roussel Pharmaceuticals Incorporated

  公开号：US05216017A1

  公开（公告）日：1993-06-01

  This invention relates to pyrrolo[2,3-b]indole ketones of the formula ##STR1## where R.sub.1 is loweralkyl, aryl or arylloweralkyl; R.sub.2 is hydrogen, halogen or loweralkyl; R.sub.3 is hydrogen or loweralkyl; R.sub.4 is loweralkyl or arylloweralkyl; R.sub.5 is hydrogen, loweralkyl, loweralkenyl, loweralkynyl, arylloweralkyl, formyl, loweralkylcarbonyl, arylloweralkylcarbonyl or loweralkoxycarbonyl; Y is hydrogen, loweralkyl or loweralkoxy; the pharmaceutically acceptable addition salts thereof, and where applicable, the geometric and optical isomers and racemic mixtures thereof. The compounds of this invention are useful in the treatment of memory impairment characterized by a cholinergic deficit such as that associated with electroshock-induced amnesia and Alzheimer's disease and other senile dementia.

  本发明涉及公式为 ##STR1## 的吡咯并[2,3-b]吲哚酮，其中R.sub.1是低烷基，芳基或芳基低烷基；R.sub.2是氢，卤素或低烷基；R.sub.3是氢或低烷基；R.sub.4是低烷基或芳基低烷基；R.sub.5是氢，低烷基，低烯基，低炔基，芳基低烷基，甲酰基，低烷基羰基，芳基低烷基羰基或低烷氧羰基；Y是氢，低烷基或低烷氧基；其药学上可接受的盐，以及适用的几何和光学异构体和外消旋混合物。本发明的化合物对于治疗记忆障碍具有用处，其特征是胆碱能缺陷，例如与电击诱导的遗忘和阿尔茨海默病以及其他老年性痴呆症有关。
• Method of preparing .alpha.-oxopyrrolo[2,3-b]indole acetic acids and
  申请人：Hoechst-Roussel Pharmaceuticals Incorporated

  公开号：US05264587A1

  公开（公告）日：1993-11-23

  This invention relates to compounds of the formula ##STR1## where X is --NH, oxygen, N-loweralkyl, or N-arylloweralkyl; R.sub.1 is hydrogen, loweralkyl, cycloalkyl, aryl, arylloweralkyl, loweralkylene, haloloweralkyl, heteroaryl selected from the group consisting of thienyl, furanyl, pyrrolyl and pyridinyl; heteroarylloweralkyl, heterocyclic selected from piperidinyl, piperazinyl, pyrrolidinyl; or heterocyclicloweralkyl; R.sub.2 is hydrogen or loweralkyl; R.sub.3 is loweralkyl or arylloweralkyl; R.sub.4 is hydrogen, loweralkyl, loweralkenyl, loweralkynyl, arylloweralkyl, formyl, loweralkylcarbonyl, arylloweralkylcarbonyl or loweralkoxycarbonyl; Y is hydrogen, loweralkyl or loweralkoxy, and the pharmaceutically acceptable acid addition salts thereof, and where applicable, the geometric and optical isomers and racemic mixtures thereof. The compounds of this invention are useful in the treatment of memory impairment characterized by a cholinergic deficit such as that associated with electroshock-induced amnesia and Alzheimer's disease and other senile dementia.

  本发明涉及以下式子的化合物：##STR1## 其中X是--NH、氧、N-较低烷基或N-芳基较低烷基；R.sub.1是氢、较低烷基、环烷基、芳基、芳基较低烷基、较低烷基亚基、卤代较低烷基、从噻吩基、呋喃基、吡咯基和吡啶基组成的杂芳基；杂芳基较低烷基、从哌啶基、哌嗪基、吡咯烷基中选择的杂环基或杂环较低烷基；R.sub.2是氢或较低烷基；R.sub.3是较低烷基或芳基较低烷基；R.sub.4是氢、较低烷基、较低烯基、较低炔基、芳基较低烷基、甲酰基、较低烷基羰基、芳基较低烷基羰基或较低烷氧羰基；Y是氢、较低烷基或较低烷氧基，以及其药学上可接受的酸盐，适用时还包括其几何和光学异构体及其外消旋混合物。本发明的化合物适用于治疗由胆碱能缺陷所表现的记忆障碍，例如与电击诱导的遗忘和老年痴呆症等相关的病症。
• Pyrrolo,[2,3-b]indole-ketones and analogs, a process for their preparation and their use as medicaments
  申请人：HOECHST-ROUSSEL PHARMACEUTICALS INCORPORATED

  公开号：EP0456196A1

  公开（公告）日：1991-11-13

  This invention relates to pyrrolo[2,3-b]indole ketones of the formula where R₁ is loweralkyl, aryl or arylloweralkyl; R₂ is hydrogen, halogen or loweralkyl; R₃ is hydrogen or loweralkyl; R₄ is loweralkyl or arylloweralkyl; R₅ is hydrogen, loweralkyl, loweralkenyl, loweralkynyl, arylloweralkyl, formyl, loweralkylcarbonyl, arylloweralkylcarbonyl or loweralkoxycarbonyl; Y is hydrogen, halogen, loweralkyl or loweralkoxy; the pharmaceutically acceptable addition salts thereof, and where applicable, the geometric and optical isomers and racemic mixtures thereof. The compounds of this invention exhibit utility for alleviating various memory dysfunctions such as Alzheimers disease.

  本发明涉及式中的吡咯并[2,3-b]吲哚酮 其中 R₁ 是低级烷基、芳基或芳基低级烷基；R₂ 是氢、卤素或低级烷基；R₃ 是氢或低级烷基；R₄ 是低级烷基或芳基低级烷基；R₅ 是氢、低级烷基、低级烯基、低级炔基、芳基低级烷基、甲酰基、低级烷基羰基、芳基低级烷基羰基或低级烷氧基羰基；Y 是氢、卤素、低级烷基或低级烷氧基；其药学上可接受的加成盐，以及（如适用）其几何异构体、光学异构体和外消旋混合物。本发明的化合物可用于缓解阿尔茨海默病等各种记忆功能障碍。
• Alpha-Oxopyrrolo[2,3-b]indole acetic acids, esters, amides and related analogs, a process for their preparation and their use as medicaments
  申请人：HOECHST-ROUSSEL PHARMACEUTICALS INCORPORATED

  公开号：EP0457318B1

  公开（公告）日：1996-08-14