eseroline | 408340-83-0

• 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: eseroline
• 英文别名: 1,3a,8-trimethyl-1,2,3,3a,8,8a-hexahydro-pyrrolo[2,3-b]indol-5-ol；(3aS-cis)-1,2,3,3a,8,8a-hexahydro-1,3a,8-trimethyl-pyrrolo[2,3-b]indol-5-ol；(3AS-cis)-1,2,3,3a,8,8a-hexahydro-1,3a,8-trimethyl-pyrrolo[2,3-b]indol-5ol；Pyrrolo[2,3-b]indol-5-ol, 1,2,3,3a,8,8a-hexahydro-1,3a,8-trimethyl-, (3aS-cis)-；3,4,8b-trimethyl-2,3a-dihydro-1H-pyrrolo[2,3-b]indol-7-ol
• CAS: 408340-83-0
• 化学式: C₁₃H₁₈N₂O
• 分子量: 218.299
• InChiKey: HKGWQUVGHPDEBZ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.8
• 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：
  26.7
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  eseroline 、 异氰酸甲酯 在 sodium hydride 作用下， 以 四氢呋喃 为溶剂， 反应 0.25h， 生成 physostigmine
  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：

  O-benzyleseroline 在 Raney-nickel W-2 作用下， 以 四氢呋喃 为溶剂， 反应 1.0h， 生成 eseroline
  参考文献：
  名称：

  The enantioselective synthesis of (-)-physostigmine via chiral sulfoxides

  摘要：

  The total synthesis of naturally occurring (-)-physostigmine is described. The key element for the asymmetric induction is the chirality transfer from optically active 2-(alkylsulfinyl)indoles to indoline butyrolactones bearing two chiral centers. Novel features of this synthesis involve the use of a new class of sulfoxylating agents, N-(alkylsulfinyl)oxazolidinones, to prepare the starting indolyl sulfoxides and the correlation of the size of the alkyl group on the sulfoxide with the degree of asymmetric induction. The overall synthesis requires a dozen steps from commercially available 5-(benzyloxy)indole.

  DOI：

  10.1021/ja00040a013

文献信息

• Memory enhancing and analgesic 1,2,3,3A,8,8A-hexahydro-3A,8 (and)
  申请人：Hoechst-Roussel Pharmaceuticals, Inc.

  公开号：US04791107A1

  公开（公告）日：1988-12-13

  There are described compounds of the formula ##STR1## where (a) X is O or S; (b) R is H, loweralkyl, ##STR2## where Y is O or S; R.sub.2 is alkyl, cycloalkyl, bicycloalkyl, cycloalkenyl, aryl, arylloweralkyl, heteroaryl or heteroarylloweralkyl, R.sub.3 is H or alkyl, or the group --NR.sub.2 R.sub.3 taken as a whole is 1-pyrrolidinyl, 1-piperidinyl, 4-morpholinyl, 4-thiomorpholinyl, 1-piperazinyl, 4-methyl-1-piperazinyl or 2-(2,6-dichlorophenylimino)-1-imidazolidinyl) and R.sub.4 is hydrogen, loweralkyl, arylloweralkyl, diarylloweralkyl, aryl or heteroaryl, (c) m is 1 or 2; (d) each Z is independently H, loweralkyl, halogen, nitro, --NH.sub.2, loweralkylcarbonylamino, arylcarbonylamino, loweralkoxycarbonylamino or loweralkylamino, and (e) R.sub.1 is H, loweralkyl, arylloweralkyl, heteroarylloweralkyl, cycloalkylmethyl or loweralkenylmethyl, with the proviso that when X is O, m is 1, Z is H and R.sub.1 is methyl, R is not --CONHCH.sub.3, --CONHC.sub.6 H.sub.5, hydrogen, methyl or ethyl, and that when X is O, m is 1 and Z and R.sub.1 are both hydrogen, R is not hydrogen or methyl, and pharmaceutically acceptable acid addition salts thereof which are useful as memory-enhancing and analgesic agents.

  描述了以下化合物的化学式##STR1## 其中（a）X为O或S；（b）R为H、loweralkyl、##STR2## 其中Y为O或S；R.sub.2为烷基、环烷基、双环烷基、环烯基、芳基、芳基loweralkyl、杂环芳基或杂环芳基loweralkyl，R.sub.3为H或烷基，或整体视为--NR.sub.2 R.sub.3时为1-吡咯基、1-哌啶基、4-吗啉基、4-硫代吗啉基、1-哌嗪基、4-甲基-1-哌嗪基或2-(2,6-二氯苯基亚胺基)-1-咪唑烷基）和R.sub.4为氢、loweralkyl、芳基loweralkyl、二芳基loweralkyl、芳基或杂环芳基，（c）m为1或2；（d）每个Z独立地为H、loweralkyl、卤素、硝基、--NH.sub.2、loweralkylcarbonylamino、arylcarbonylamino、loweralkoxycarbonylamino或loweralkylamino，（e）R.sub.1为H、loweralkyl、芳基loweralkyl、杂环芳基loweralkyl、环烷基甲基或loweralkenylmethyl，但当X为O时，m为1、Z为H且R.sub.1为甲基时，R不是--CONHCH.sub.3、--CONHC.sub.6 H.sub.5、氢、甲基或乙基，当X为O时，m为1且Z和R.sub.1均为氢时，R不是氢或甲基，以及其药用可接受的酸盐，可用作增强记忆和镇痛剂。
• Compound useful in the treatment or prevention of cognitive disorders associated with diabetes and associated methods
  申请人：Greig H. Nigel

  公开号：US20060105940A1

  公开（公告）日：2006-05-18

  Described is the efficient synthesis of an easy to manipulate and utilize, soluble tartrate salt of a potent, reversible butyrylcholinesterase inhibitor, (−)-(3aS)-3a-methyl-1,2,3,3a,8,8a-hexahydropyrrolo-[2,3-b]indol-5-yl N—4′-isopropylphenylcarbamate (“MHI tartrate”), for use in altering the enzymatic activity of butyrylcholinesterase and/or acetylcholinesterase in a subject exhibiting or predicted to exhibit cognitive disorders associated with diabetes. Subjects may be suffering from or predicted to suffer from abnormal acetylcholinesterase and/or butyrylcholinesterase activity levels or from an inability to metabolize or catabolize blood sugar normally. The method comprises administering to the subject an effective amount of MHI tartrate dispensable in discrete pharmaceutically useful dosages. MHI tartrate effectively inhibits both acetylcholinesterase and butyrylcholinesterases and additionally is highly selective for butyrylcholinesterase over acetylcholinesterase.

  描述了一种高效合成易于操纵和利用的可溶性酒石酸盐，用作对展现或预测将展现与糖尿病相关的认知障碍的受试者中的丁酰胆碱酯酶和/或乙酰胆碱酯酶的酶活性进行改变的药物，该药物是一种有效的、可逆的丁酰胆碱酯酶抑制剂，(−)-(3aS)-3a-甲基-1,2,3,3a,8,8a-六氢吡咯并-[2,3-b]吲哚-5-基-N-4'-异丙基苯甲酸酯（“MHI酒石酸盐”）。受试者可能正在受苦于或预测将受苦于异常的乙酰胆碱酯酶和/或丁酰胆碱酯酶活性水平，或者由于无法正常代谢或降解血糖。该方法包括向受试者投予MHI酒石酸盐的有效量，可分配为离散的药用剂量。MHI酒石酸盐有效地抑制了乙酰胆碱酯酶和丁酰胆碱酯酶，并且对丁酰胆碱酯酶的选择性高于对乙酰胆碱酯酶的选择性。
• Therapeutic agent for overactive bladder involved in aging
  申请人：Yokoyama Osamu

  公开号：US20060135507A1

  公开（公告）日：2006-06-22

  A method for treating overactive bladder involved in aging, comprising administrating a compound having a cholinesterase inhibitory activity, a pharmacologically acceptable salt or a solvate thereof to a patient with the overactive bladder involved in aging.

  一种治疗老年人过度活跃膀胱的方法，包括向患有老年人过度活跃膀胱的患者施用具有胆碱酯酶抑制活性的化合物、药理学上可接受的盐或其溶剂。
• Therapeutic agent for overactive bladder resulting from cerebral infarction
  申请人：Yokoyama Osamu

  公开号：US20060172992A1

  公开（公告）日：2006-08-03

  An agent for treating overactive bladder resulting from cerebral infarction, comprising administrating a compound having a cholinesterase inhibitory activity or a pharmacologically acceptable salt thereof.

  一种用于治疗因脑梗死引起的过度活动膀胱的制剂，包括给予具有胆碱酯酶抑制活性或其药理学上可接受的盐的化合物。
• Carbamoyl esters that inhibit cholinesterase and release pharmacologically active agents
  申请人：Verheijen C. Jeroen

  公开号：US20050096387A1

  公开（公告）日：2005-05-05

  Carbamoyl esters inhibit cholinesterase activity and, upon hydrolysis release a pharmacologically active agent. In one embodiment, the carbamoyl ester has the following structure: wherein A is selected from the group consisting of an unsubstituted aryl, a substituted aryl, an unsubstituted heteroaryl and a substituted heteroaryl. The carbamoyl esters are employed in methods to treat an individual. The pharmacologically active agent obtained by hydrolysis of the carbamoyl esters can treat, for example, a nervous system condition, a cholinergic deficiency and conditions or diseases associated with a deficiency in a pharmacologically active agent, such as acetylcholine.

  碳酰基酯抑制胆碱酯酶活性，水解后释放出药理活性成分。在一种实施例中，碳酰基酯具有以下结构：其中A选自无取代芳基、取代芳基、无取代杂环芳基和取代杂环芳基的群组。碳酰基酯用于治疗个体的方法中。通过水解碳酰基酯获得的药理活性成分可以治疗例如神经系统疾病、胆碱能缺乏以及与药理活性成分缺乏相关的疾病或病症，例如乙酰胆碱。