6-hydroxy-2,5,7,8-tetramethyl-N-(2-(pyridin-2-yl)ethyl)chroman-2-carboxamide

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并吡喃
• 英文名称: 6-hydroxy-2,5,7,8-tetramethyl-N-(2-(pyridin-2-yl)ethyl)chroman-2-carboxamide
• 英文别名: 6-hydroxy-2,5,7,8-tetramethyl-N-(2-pyridin-2-ylethyl)-3,4-dihydrochromene-2-carboxamide
• 化学式: C₂₁H₂₆N₂O₃
• 分子量: 354.449
• InChiKey: ZDNGYFKANRDTCD-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  26
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.43
• 拓扑面积：
  71.4
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  6-hydroxy-2,5,7,8-tetramethyl-N-(2-(pyridin-2-yl)ethyl)chroman-2-carboxamide 在 ammonium cerium(IV) nitrate 、 水 作用下， 以 二氯甲烷 、 乙腈 为溶剂， 生成 2-hydroxy-2-methyl-N-(pyridin-2-ylmethyl)-4-(2,4,5-trimethyl-3,6-dioxocyclohexa-1,4-dienyl)butanamide
  参考文献：
  名称：

  4-(p-QUINONYL)-2-HYDROXYBUTANAMIDE DERIVATIVES FOR TREATMENT OF MITOCHONDRIAL DISEASES

  摘要：

  揭示了治疗或抑制线粒体疾病的方法，例如弗里德雷希共济失调症（FRDA）、勒伯遗传性视神经病变（LHON）、线粒体肌病、脑病、乳酸中毒和中风（MELAS）、科恩斯-萨耶综合征（KSS），以及在本发明方法中有用的化合物，如4-(对喹啉基)-2-羟基丁酰胺衍生物。还揭示了用于治疗其他疾病的方法和化合物，如肌萎缩侧索硬化症（ALS）、亨廷顿病、帕金森病和广泛性发展障碍如自闭症。还揭示了用于评估受试者代谢状态和治疗疗效的能量生物标志物。还揭示了调节、规范或增强能量生物标志物的方法，以及用于这些方法的化合物。

  公开号：

  US20090118257A1
• 作为产物：
  描述：

  2-(2-甲基氨基乙基)吡啶 、 奎诺二甲基丙烯酸酯 在 N,N'-羰基二咪唑 作用下， 以 四氢呋喃 为溶剂， 反应 1.0h， 生成 6-hydroxy-2,5,7,8-tetramethyl-N-(2-(pyridin-2-yl)ethyl)chroman-2-carboxamide
  参考文献：
  名称：

  4-(p-QUINONYL)-2-HYDROXYBUTANAMIDE DERIVATIVES FOR TREATMENT OF MITOCHONDRIAL DISEASES

  摘要：

  揭示了治疗或抑制线粒体疾病的方法，例如弗里德雷希共济失调症（FRDA）、勒伯遗传性视神经病变（LHON）、线粒体肌病、脑病、乳酸中毒和中风（MELAS）、科恩斯-萨耶综合征（KSS），以及在本发明方法中有用的化合物，如4-(对喹啉基)-2-羟基丁酰胺衍生物。还揭示了用于治疗其他疾病的方法和化合物，如肌萎缩侧索硬化症（ALS）、亨廷顿病、帕金森病和广泛性发展障碍如自闭症。还揭示了用于评估受试者代谢状态和治疗疗效的能量生物标志物。还揭示了调节、规范或增强能量生物标志物的方法，以及用于这些方法的化合物。

  公开号：

  US20090118257A1

文献信息

• 4-(p-quinonyl)-2-hydroxybutanamide derivatives for treatment of mitochondrial diseases
  申请人：Edison Pharmaceuticals, Inc.

  公开号：US07968746B2

  公开（公告）日：2011-06-28

  Methods of treating or suppressing mitochondrial diseases, such as Friedreich's ataxia (FRDA), Leber's Hereditary Optic Neuropathy (LHON), mitochondrial myopathy, encephalopathy, lactacidosis, and stroke (MELAS), Kearns-Sayre Syndrome (KSS), are disclosed, as well as compounds useful in the methods of the invention, such as 4-(p-quinolyl)-2-hydroxybutanamide derivatives. Methods and compounds useful in treating other disorders such as amyotrophic lateral sclerosis (ALS), Huntington's disease, Parkinson's disease, and pervasive developmental disorders such as autism are also disclosed. Energy biomarkers useful in assessing the metabolic state of a subject and the efficacy of treatment are also disclosed. Methods of modulating, normalizing, or enhancing energy biomarkers, as well as compounds useful for such methods, are also disclosed.

  本发明公开了治疗或抑制线粒体疾病的方法，如弗里德赫氏共济失调症（FRDA）、勒伯遗传性视神经病变（LHON）、线粒体肌病、脑病、乳酸中毒和中风（MELAS）、基恩斯-塞尔综合症（KSS），以及在本发明方法中有用的化合物，如4-(p-喹啉基)-2-羟基丁酰胺衍生物。本发明还公开了治疗其他疾病，如肌萎缩性侧索硬化症（ALS）、亨廷顿病、帕金森病和广泛性发育障碍，如自闭症的方法和化合物。本发明还公开了用于评估受试者代谢状态和治疗效果的能量生物标志物。本发明还公开了调节、规范或增强能量生物标志物的方法，以及用于此类方法的化合物。
• Pharmaceutically active amines
  申请人：THE UPJOHN COMPANY

  公开号：EP0487510A1

  公开（公告）日：1992-05-27

  Bicyclic amines (III), are useful as pharmaceutical agents for treating a number of conditions including spinal trauma, mild and/or moderate to severe head injury, etc.

  双环胺 (III)、 可用作治疗多种疾病的药物，包括脊柱创伤、轻度和/或中重度头部损伤等。
• 4-(P-quinonyl)-2-hydroxybutanamide derivatives for treatment of mitochondrial diseases
  申请人：PTC Therapeutics, Inc.

  公开号：US10968166B2

  公开（公告）日：2021-04-06

  Methods of treating or suppressing mitochondrial diseases, such as Friedreich's ataxia (FRDA), Leber's Hereditary Optic Neuropathy (LHON), mitochondrial myopathy, encephalopathy, lactacidosis, and stroke (MELAS), Kearns-Sayre Syndrome (KSS), are disclosed, as well as compounds useful in the methods of the invention, such as 4-(p-quinoly)-2-hydroxybutanamide derivatives. Methods and compounds useful in treating other disorders such as amyotrophic lateral sclerosis (ALS), Huntington's disease, Parkinson's disease, and pervasive developmental disorders such as autism are also disclosed. Energy biomarkers useful in assessing the metabolic state of a subject and the efficacy of treatment are also disclosed. Methods of modulating, normalizing, or enhancing energy biomarkers, as well as compounds useful for such methods, are also disclosed.

  本发明公开了治疗或抑制线粒体疾病的方法，如弗里德雷氏共济失调（FRDA）、勒伯氏遗传性视神经病变（LHON）、线粒体肌病、脑病、乳酸中毒和中风（MELAS）、卡恩斯-赛尔综合征（KSS），以及用于本发明方法的化合物，如4-（对-喹啉基）-2-羟基丁酰胺衍生物。本发明还公开了用于治疗其他疾病的方法和化合物，如肌萎缩性脊髓侧索硬化症（ALS）、亨廷顿氏病、帕金森氏病和广泛性发育障碍，如自闭症。还公开了有助于评估受试者代谢状态和治疗效果的能量生物标记物。还公开了调节、正常化或增强能量生物标志物的方法以及用于此类方法的化合物。
• 2-(Aminomethyl)chromans that inhibit iron-dependent lipid peroxidation and protect against central nervous system trauma and ischemia
  作者：E. Jon Jacobsen、Fred J. VanDoornik、Donald E. Ayer、Kenneth L. Belonga、J. Mark Braughler、Edward D. Hall、David J. Houser

  DOI：10.1021/jm00101a025

  日期：1992.11

  A series of 2-(aminomethyl)chromans was developed as potent inhibitors of iron-dependent lipid peroxidation. Compounds within this class are extremely effective at inhibiting lipid peroxidation with IC50's as low as 0.2 muM. Selected members were found to enhance early neurological recovery and survival in a mouse head injury model. In this assay, improvement in the 1-h post-head-injury neurological status (grip test score) by as much as 230 % of control was observed. One of the most efficacious compounds (35) was evaluated in two models of cerebral ischemia where significant neuroprotection was observed. These results provide further support for the importance of cerebroprotective antioxidants for the treatment of traumatic and ischemic injury as well as additional evidence for the role of oxygen radicals in postischemic brain damage.
• 4- (P-QUINONYL)-2-HYDROXYBUTANAMIDE DERIVATIVES FOR TREATMENT OF MITOCHONDRIAL DISEASES
  申请人：Edison Pharmaceuticals, Inc.

  公开号：EP2220030A2

  公开（公告）日：2010-08-25