1-methyl-2-(3,7,8,9-tetrahydro-pyrano[3,2-e]indol-1-yl)-ethylamine | 362603-40-5

• 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: 1-methyl-2-(3,7,8,9-tetrahydro-pyrano[3,2-e]indol-1-yl)-ethylamine
• 英文别名: 1-(3,7,8,9-tetrahydropyrano[3,2-e]indol-1-yl)propan-2-amine
• CAS: 362603-40-5
• 化学式: C₁₄H₁₈N₂O
• 分子量: 230.31
• InChiKey: VVHJUSGIUWQPIT-UHFFFAOYSA-N

物化性质

• 沸点：
  437.1±40.0 °C(Predicted)
• 密度：
  1.192±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  17
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.43
• 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：

  1-methyl-2-(3,7,8,9-tetrahydro-pyrano[3,2-e]indol-1-yl)-ethylamine 在 盐酸 作用下， 以 乙醚 、 乙醇 为溶剂， 生成 1-(2-aminopropyl)-8,9-dihydropyrano[3,2-e]indole hydrochloride
  参考文献：
  名称：

  PYRANOINDOLES FOR TREATING GLAUCOMA

  摘要：

  公开号：

  EP1268482A1
• 作为产物：
  描述：

  8,9-dihydropyrano<3,2-e>indole-1-carboxaldehyde 在 lithium aluminium tetrahydride 、 ammonium acetate 作用下， 以 四氢呋喃 为溶剂， 反应 5.0h， 生成 1-methyl-2-(3,7,8,9-tetrahydro-pyrano[3,2-e]indol-1-yl)-ethylamine
  参考文献：
  名称：

  A Novel and Selective 5-HT₂ Receptor Agonist with Ocular Hypotensive Activity:  (S)-(+)-1-(2-Aminopropyl)-8,9-dihydropyrano[3,2-e]indole

  摘要：

  Serotonin 5-HT2 receptor agonists have recently been shown to be effective, in lowering intraocular pressure in nonhuman primates and represent a potential new class of antiglaucoma agents. As part of an effort to identify new selective agonists at this receptor, we have found that (S)-(+)-l-(2-aminopropyl)-8,9-dihydropyrano[3,2-e]indole (AL-37350A, 11) has high affinity and selectivity (> 1000-fold) for the 5-HT2 receptor relative to other 5-HT receptors. More specifically, 11 is a potent agonist at the 5-HT2A receptor (EC50 = 28.6 nM, E-max = 103%) that is comparable to serotonin. Evaluation of 11 in conscious ocular hypertensive cynomolgus monkeys showed this compound to be efficacious in reducing intraocular pressure (13.1 mmHg, -37%). Thus, 11 is a potent full agonist with selectivity for the 5-HT2 receptor and is anticipated to serve as a useful tool in exploring the role of the 5-HT2 receptor and its effector system in controlling intraocular pressure.

  DOI：

  10.1021/jm030205t

文献信息

• Synthesis of novel serotonergics and other N-alkylamines using simple reductive amination using catalytic hydrogenation with Pd/C
  作者：George N. Karageorge、John E. Macor

  DOI：10.1016/j.tetlet.2011.07.058

  日期：2011.10

  Formation of N-alkylated α-methyltryptamine derivatives (2) was accomplished by simple reductive amination of amine (1) with ketones using catalytic hydrogenation conditions (3 atm H2 and 10% Pd on carbon). This method was also applied to other primary and secondary amines using ketones and aldehydes.

  N-烷基化的α-甲基色胺衍生物（2）的形成是通过在催化氢化条件下（3 atm H 2和碳上含10％Pd ）对胺（1）进行简单的胺酮还原胺化而完成的。该方法也适用于使用酮和醛的其他伯胺和仲胺。
• PHARMACEUTICAL COMPOSITION COMPRISING AN AMPK ACTIVATOR AND A SEROTONERGIC AGENT AND METHODS OF USE THEREOF
  申请人：ALS Mountain Llc

  公开号：EP2983473A2

  公开（公告）日：2016-02-17
• NOVEL COMPOSITION FOR TREATING METABOLIC SYNDROME AND OTHER CONDITIONS
  申请人：Chen Chien-Hung

  公开号：US20120183600A1

  公开（公告）日：2012-07-19

  The invention relates to a composition that includes a first agent selected from the group consisting of an oxidative phosphorylation inhibitor, an ionophore, and an adenosine 5′-monophosphate-activated protein kinase (AMPK) activator; a second agent that possesses anti-inflammatory activity; and a third agent that possesses serotonin activity.
• US7012090B1
  申请人：——

  公开号：US7012090B1

  公开（公告）日：2006-03-14
• [EN] PHARMACEUTICAL COMPOSITION COMPRISING AN AMPK ACTIVATOR AND A SEROTONERGIC AGENT AND METHODS OF USE THEREOF<br/>[FR] COMPOSITION PHARMACEUTIQUE COMPRENANT UN ACTIVATEUR D'AMPK ET UN AGENT SÉROTONINERGIQUE ET PROCÉDÉS D'UTILISATION CORRESPONDANTS
  申请人：ALS MOUNTAIN LLC

  公开号：WO2014144130A2

  公开（公告）日：2014-09-18

  The present invention is based on the unexpected discovery that a combination of certain known drugs exhibits synergistic effects in treating metabolic syndrome and various other diseases. In particular, the invention comprises a pharmaceutical composition comprising: (1) a therapeutically effective quantity of a first agent that is an AMPK activator; and (2) a therapeutically effective quantity of a second agent that possesses or maintains serotonin activity. A preferred composition comprises metformin hydrochloride and melatonin. The invention further comprises methods for the use of these compositions for the treatment of metabolic syndrome, hyperproliferative diseases including cancer, and other diseases and conditions.