(5-(benzyloxy)-1H-indol-2-yl)methanamine | 133845-48-4

• 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-(benzyloxy)-1H-indol-2-yl)methanamine
• 英文别名: PF9601N-M；(5-phenylmethoxy-1H-indol-2-yl)methanamine
• CAS: 133845-48-4
• 化学式: C₁₆H₁₆N₂O
• 分子量: 252.316
• InChiKey: SEZDPZNQVYRBAF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  19
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  51
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (5-(benzyloxy)-1H-indol-2-yl)methanamine 在 palladium on activated charcoal 氢气 、 溶剂黄146 、 叔丁胺 作用下， 以 四氢呋喃 为溶剂， 25.0 ℃ 、101.33 kPa 条件下， 反应 5.0h， 生成 2-(Di-prop-2-ynyl-aminomethyl)-1H-indol-5-ol
  参考文献：
  名称：

  Acetylenic and allenic derivatives of 2-(5-benzyloxyindolyl) and 2-(5-hydroxyindolyl)methylamines: synthesis and in vitro evaluation as monoamine oxidase inhibitors

  摘要：

  We report the synthesis and in vitro studies as MAO inhibitors of 2 series of new acetylenic and allenic derivatives of 2-(5-benzyloxyindolyl)- and 2-(5-hydroxyindolyl)methylamines and their indolylmethylamine precursors. All compounds were MAO inhibitors and either did not show selectivity (the benzyloxy compounds 5) or were selective for MAO-A (most of the hydroxy compounds 7). Three of the studied compounds, 7d, 7g and 7i, were found to be slightly more selective for MAO-A than clorgyline.

  DOI：

  10.1016/0223-5234(91)90210-e
• 作为产物：
  描述：

  2-(5-benzyloxyindole)carboxamide 在 lithium aluminium tetrahydride 作用下， 以 四氢呋喃 为溶剂， 以99 %的产率得到(5-(benzyloxy)-1H-indol-2-yl)methanamine
  参考文献：
  名称：

  [EN] NOVEL INDOLE DERIVATIVE, AND USE THEREOF FOR TREATING DISEASES RELATED TO ADVANCED GLYCATION END PRODUCTS
  [FR] NOUVEAU DÉRIVÉ D'INDOLE ET SON UTILISATION POUR LE TRAITEMENT DE MALADIES LIÉES À DES PRODUITS FINAUX DE GLYCATION AVANCÉE
  [KO] 신규한 인돌 유도체 및 이의 최종당화산물 관련 질환의 치료 용도

  摘要：

  본 발명은 신규한 인돌 유도체 및 이의 용도에 관한 것이다. 본 발명의 신규한 인돌 유도체는 최종당화산물의 주요 전구체인 메틸글리옥살(methylglyoxal: MGO)을 포획하므로, 최종당화산물과 관련된 질병의 예방, 개선 또는 치료에 유용하게 사용될 수 있다.

  公开号：

  WO2022260491A1

文献信息

• 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。
• PHARMACEUTICAL COMPOSITIONS BASED ON AMINOMETHYLINDOLES AND THEIR THERAPEUTICAL APPLICATION AS NEUROPROTECTORS IN PARKINSON AND ALZHEIMER DISEASES
  申请人：CONSEJO SUPERIOR INVESTIGACIONES CIENTIFICAS (CSIC)

  公开号：EP0754455A1

  公开（公告）日：1997-01-22

  Pharmaceutical compositions containing as active components 2-aminomethyl-5-benzyloxyindoles derivatives, including the N-propinyl, N-2-butinyl and N-2,3-butadinylderivatives which are potent inhibitors of monoaminoxydase A and B of rat liver and brain, as well as of the human brain, with marked selectivity for the in vitro and in vivo inhibition of monoaminoxydase B, preferably on the A. In relation to said selectivity of inhibition of monoaminoxydase B, as well as to their capacity to neutralize in laboratory animals the neurotoxic action of MPTP and other neurotoxines, the disclosed compounds are useful for the treatment of cerebral neurodegenerative processes, and particularly for the treatment of Parkinson and Alzheimer diseases.

  含有作为活性成分的 2-氨基甲基-5-苄氧基吲哚衍生物的药物组合物，包括 N-丙基、N-2-丁基和 N-2,3-丁基二羟基衍生物，它们是大鼠肝脏和大脑以及人脑中单胺氧化酶 A 和 B 的强效抑制剂，对体外和体内单胺氧化酶 B 具有明显的选择性抑制作用，尤其是对 A 的抑制作用。鉴于上述抑制单胺氧化酶 B 的选择性，以及其在实验动物体内中和 MPTP 和其他神经毒素的神经毒性作用的能力，所公开的化合物可用于治疗脑神经变性过程，特别是帕金森病和阿尔茨海默病的治疗。
• CARBAMOYL ESTERS THAT INHIBIT CHOLINESTERASE AND RELEASE PHARMACOLOGICALLY ACTIVE AGENTS
  申请人：CoLucid Pharmaceuticals, Inc.

  公开号：EP1689704A2

  公开（公告）日：2006-08-16
• COMPOUNDS THAT INHIBIT CHOLINESTERASE
  申请人：Colucid Pharmaceuticals, Inc.

  公开号：EP2125709A2

  公开（公告）日：2009-12-02
• Carbamoyl Esters That Inhibit Cholinesterase And Release Pharmacologically Active Agents
  申请人：Verheijen C. Jeroen

  公开号：US20070275959A1

  公开（公告）日：2007-11-29

  Carbamoyl esters inhibit cholinesterase activity and, upon hydrolysis release a pharmacologically active agent. In one embodiment, the carbamoyl ester has the following structure: Formula (I) 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.