(6r)-3-Methoxy-5,6,9,10,11,12-hexahydro-4ah-[1]benzofuro[3a,3,2-ef][2]benzazepin-6-ol

• 分子结构分类: 有机化合物 - 生物碱及其衍生物 - 石蒜科生物碱
• 英文名称: (6r)-3-Methoxy-5,6,9,10,11,12-hexahydro-4ah-[1]benzofuro[3a,3,2-ef][2]benzazepin-6-ol
• 英文别名: (14R)-9-methoxy-11-oxa-4-azatetracyclo[8.6.1.01,12.06,17]heptadeca-6(17),7,9,15-tetraen-14-ol
• 化学式: C₁₆H₁₉NO₃
• 分子量: 273.332
• InChiKey: AIXQQSTVOSFSMO-XOMBGVMMSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  20
• 可旋转键数：
  1
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  50.7
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  无水氯化钙 、 (4α,6β)-4a,5,9,10,11,12-hexhydro-3-methoxy-6H-benzofuro[3a,3,2-ef][2]benzazepin-6-ol 在 锌 盐酸 、 乙酸乙酯 、 二氯甲烷 、 Brine 、 Sodium sulfate-III 作用下， 以 乙醇 为溶剂， 反应 18.0h， 以to produce 12.3 g (79.0% of compound 4的产率得到(6r)-3-Methoxy-5,6,9,10,11,12-hexahydro-4ah-[1]benzofuro[3a,3,2-ef][2]benzazepin-6-ol
  参考文献：
  名称：

  Derivatives and analogs of galanthamine

  摘要：

  新的化合物，通式为I。

  公开号：

  US20070027138A1

文献信息

• Novel derivatives and analogues of galanthamin
  申请人：——

  公开号：US20030199493A1

  公开（公告）日：2003-10-23

  New compounds of general formula I 1

  通式I1的新化合物
• CHOLINERGIC ENHANCERS WITH IMPROVED BLOOD-BRAIN BARRIER PERMEABILITY FOR THE TREATMENT OF DISEASES ACCOMPANIED BY COGNITIVE IMPAIRMENT
  申请人：Maelicke Alfred

  公开号：US20070213318A1

  公开（公告）日：2007-09-13

  The present invention refers to compounds that, in addition to enhancing the sensitivity to acetylcholine and choline of neuronal cholinergic receptors and/or acting as cholinesterase inhibitors and/or neuroprotective agents, have enhanced blood-brain barrier permeability in comparison to their parent compounds. The compounds are derived (either formally by their chemical structure or directly by chemical synthesis) from natural compounds belonging to the class of amaryllidaceae alkaloids e.g. galanthamine, narwedine and lycoramine, or from metabolites of said compounds. The compounds of the present invention can either interact as such with their target molecules, or they can act as “pro-drugs”, in the sense that after reaching their target regions in the body they are converted by hydrolysis or enzymatic attack to the original parent compound and react as such with their target molecules, or both. The compounds of this invention may be used as medicaments for the treatment of human brain diseases associated with a cholinergic deficit, including the neurodegenerative diseases Alzheimer's and Parkinson's disease and the psychiatric diseases vascular dementia, schizophrenia and epilepsy.

  本发明涉及化合物，除了增强神经元胆碱能受体对乙酰胆碱和胆碱的敏感性，或者作为胆碱酯酶抑制剂和/或神经保护剂外，与其母化合物相比，具有增强的血脑屏障渗透性。这些化合物是从天仙子科生物碱类天仙子碱，如无心菜碱、纳尔韦丁和百合碱，或其代谢物中派生的（通过其化学结构或直接通过化学合成）。本发明的化合物可以直接与其目标分子相互作用，也可以作为“前药”，在到达体内目标区域后，通过水解或酶攻击转化为原始母化合物，并像母化合物一样与其目标分子反应，或两者兼而有之。本发明的化合物可用作治疗与胆碱能缺陷相关的人类脑疾病的药物，包括神经退行性疾病阿尔茨海默病和帕金森病以及精神疾病血管性痴呆、精神分裂症和癫痫。
• Cholinergic Enhancers with Improved Blood-Brain Barrier permeability for the Treatment of Diseases Accompanied by Cognitive Impairment
  申请人：Maelicke Alfred

  公开号：US20080261954A1

  公开（公告）日：2008-10-23

  The present invention refers to compounds that, in addition to enhancing the sensitivity to acetylcholine and choline, and their exogenous agonists, of neuronal cholinergic receptors and/or acting as cholinesterase inhibitors and/or neuroprotective agents, have enhanced blood-brain barrier permeability in comparison to their parent compounds. The compounds are derived (either formally by their chemical structure or directly by chemical synthesis) from natural compounds belonging to the class of amaryllidaceae alkaloids e.g. Galanthamine, narwedine and lycoramine, or from metabolites of said compounds.

  本发明涉及一种化合物，除了增强神经元胆碱能受体及外源性激动剂对乙酰胆碱和胆碱的敏感性，以及作为胆碱酯酶抑制剂和/或神经保护剂外，还具有比其母体化合物更强的血脑屏障通透性。这些化合物是从天仙子科生物碱（例如迎春花碱，纳威丁和莲花碱）或其代谢物中衍生出来的（可以通过其化学结构或直接通过化学合成来实现）。
• Cholinergic enhancers with improved blood-brain barrier permeability for the treatment of diseases accompanied by cognitive impairment
  申请人：NEURODYN LIFE SCIENCES INC.

  公开号：US10265325B2

  公开（公告）日：2019-04-23

  A method for the treatment of a neurodegenerative, psychiatric or neurological disease associated with a cholinergic deficit comprising administering GLN-1062 or a pharmaceutically acceptable salt thereof by nasal administration to a patient in need thereof.

  一种治疗与胆碱能不足有关的神经退行性疾病、精神疾病或神经系统疾病的方法，包括通过鼻腔给药给有需要的患者施用 GLN-1062 或其药学上可接受的盐。
• NEUE DERIVATE UND ANALOGA VON GALANTHAMIN
  申请人：Sanochemia Pharmazeutika Aktiengesellschaft

  公开号：EP1181294B1

  公开（公告）日：2004-03-31