2,3,4,9-Tetrahydro-2-methyl-9-(phenylmethyl)-1H-pyrido<3,4-b>indole | 112800-07-4

• 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: 2,3,4,9-Tetrahydro-2-methyl-9-(phenylmethyl)-1H-pyrido<3,4-b>indole
• 英文别名: 9-benzyl-2-methyl-2,3,4,9-tetrahydro-1H-β-carboline；9-Benzyl-2-methyl-2,3,4,9-tetrahydro-1H-β-carbolin；9-benzyl-2-methyl-2,3,4,9-tetrahydro-1H-beta-carboline；9-benzyl-2-methyl-3,4-dihydro-1H-pyrido[3,4-b]indole
• CAS: 112800-07-4
• 化学式: C₁₉H₂₀N₂
• 分子量: 276.381
• InChiKey: ZJMCGGAWSAXHNR-UHFFFAOYSA-N

物化性质

• 沸点：
  457.3±33.0 °C(Predicted)
• 密度：
  1.12±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  21
• 可旋转键数：
  2
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.26
• 拓扑面积：
  8.2
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为产物：
  描述：

  [2-(1-benzyl-indol-3-yl)-ethyl]-methyl-amine; hydrochloride 在 聚合甲醛 、 水 作用下， 生成 2,3,4,9-Tetrahydro-2-methyl-9-(phenylmethyl)-1H-pyrido<3,4-b>indole
  参考文献：
  名称：

  Pyridindoles and method of manufacture

  摘要：

  公开号：

  US02642438A1

文献信息

• Indoles, IV 9-Substituted 4,9-Dihydropyrano[3,4-b]indol-1(3H)-ones - Synthesis and Conversion into 2,3,4,9-Tetrahydro- 1H-pyrido-[3,4-b]indoles
  作者：Adel A. El-Gendy、Jochen Lehmann

  DOI：10.1002/ardp.19873200806

  日期：——

  Pyrano[3,4‐b]indolones 3a‐d are available from α‐ethoxyalyllactones 1a, c and disubstituted hydrazines 2a, b without isolation of intermediates. In a two‐phase system, however, the intermediate hydrazones 4a, c can be isolated. Conversion of 3a‐d into β‐carbolines was not possible by lactamisation but via the amides 8 and 9.

  Pyrano [3,4-b] indolones 3a-d 可从 α-乙氧基烯丙基内酯 1a、c 和二取代肼 2a、b 获得，无需分离中间体。然而，在两相系统中，可以分离中间腙4a、c。3a-d 转化为 β-咔啉不可能通过内酰胺化，而是通过酰胺 8 和 9。
• Methods and compositions for treating degenerative and ischemic disorders
  申请人：The General Hospital Corporation

  公开号：US10322122B2

  公开（公告）日：2019-06-18

  Model systems have shown that shifting a cell's reliance from oxidative phosphorylation (OXPHOS) to glycolysis can protect against cell death. Exploiting the therapeutic potential of this strategy, however, has been limited by the lack of clinically safe agents that remodel energy metabolism. The present invention identifies non-toxic small molecules (e.g., drug-like compounds) that are capable of modulating oxidative metabolism. One identified compound comprises meclizine. As described herein, meclizine, and its enantiomer S-meclizine, redirects OXPHOS to glycolysis. Such compounds could be protective or therapeutic in degenerative disorders such as diabetes, Huntington's, Parkinson's, and Alzheimer's disease and/or ischemic disorders including, but not limited to, stroke, heart attack, or reperfusion injuries.

  模型系统显示，将细胞对氧化磷酸化（OXPHOS）的依赖转移到糖酵解，可以防止细胞死亡。然而，由于缺乏重塑能量代谢的临床安全药物，这一策略的治疗潜力一直受到限制。本发明确定了能够调节氧化代谢的无毒小分子（如药物样化合物）。其中一种已确定的化合物包括麦考嗪。如本文所述，麦考嗪及其对映体 S-麦考嗪可将 OXPHOS 重定向至糖酵解。这类化合物对退化性疾病，如糖尿病、亨廷顿氏病、帕金森氏病和阿尔茨海默氏症和/或缺血性疾病，包括但不限于中风、心脏病发作或再灌注损伤具有保护或治疗作用。
• METHODS AND COMPOSITIONS FOR TREATING DEGENERATIVE AND ISCHEMIC DISORDERS
  申请人：The General Hospital Corporation

  公开号：US20180071279A1

  公开（公告）日：2018-03-15

  Model systems have shown that shifting a cell's reliance from oxidative phosphorylation (OXPHOS) to glycolysis can protect against cell death. Exploiting the therapeutic potential of this strategy, however, has been limited by the lack of clinically safe agents that remodel energy metabolism. The present invention identifies non-toxic small molecules (e.g., drug-like compounds) that are capable of modulating oxidative metabolism. One identified compound comprises meclizine. As described herein, meclizine, and its enantiomer S-meclizine, redirects OXPHOS to glycolysis. Such compounds could be protective or therapeutic in degenerative disorders such as diabetes, Huntington's, Parkinson's, and Alzheimer's disease and/or ischemic disorders including, but not limited to, stroke, heart attack, or reperfusion injuries.