6-decyl-1,4-dimethyl-2,3-dihydro-1H-pyrrolo[2,3-b]pyridine-5-ol | 1380414-81-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯并吡啶类
• 英文名称: 6-decyl-1,4-dimethyl-2,3-dihydro-1H-pyrrolo[2,3-b]pyridine-5-ol
• 英文别名: 6-Decyl-1,4-dimethyl-2,3-dihydropyrrolo[2,3-b]pyridin-5-ol
• CAS: 1380414-81-2
• 化学式: C₁₉H₃₂N₂O
• 分子量: 304.476
• InChiKey: PDIRDFYSHKXJHC-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.3
• 重原子数：
  22
• 可旋转键数：
  9
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.74
• 拓扑面积：
  36.4
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  6-decyl-1,4-dimethyl-2,3-dihydro-1H-pyrrolo[2,3-b]pyridine-5-ol 、 乙酸酐 在 4-二甲氨基吡啶 、 三乙胺 作用下， 以 四氢呋喃 、 hexanes 为溶剂， 反应 1.0h， 以28 mg的产率得到1,4-dimethyl-6-decyl-2,3-dihydro-1H-pyrrolo[2,3-b]pyridin-5-yl acetate
  参考文献：
  名称：

  Simplified bicyclic pyridinol analogues protect mitochondrial function

  摘要：

  Bicyclic pyridinol antioxidants have been reported to suppress the autoxidation of methyl linoleate more effectively than alpha-tocopherol in benzene solution. A few novel lipophilic analogues have recently been synthesized by conjugating a pyridinol core with the phytyl side chain of alpha-tocopherol; these have been shown to possess potent antioxidant activity. However, the complexity of the synthetic routes has hampered their further development. Herein, we describe a facile approach, involving only five synthetic steps, to simplified analogues (1a-1c) and their acetate ester precursors (2a-2c). Simple alkyl chains of different lengths were attached to the 6-methyl group of the antioxidant core via regioselective metalation. These analogues were found to retain biological activity and exhibit protective behaviour under conditions of induced oxidative stress, which could lead to the development of more readily accessible analogues as potential antioxidants capable of preserving mitochondrial function. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2012.03.075
• 作为产物：
  描述：

  4-氨基-3-戊烯-2-酮 在 过氧乙酸 、 正丁基锂 、 1,3-二溴-5,5-二甲基海因 、 四甲基乙二胺 作用下， 以 四氢呋喃 、 hexanes 、 氯仿 、 甲苯 为溶剂， 反应 36.5h， 生成 6-decyl-1,4-dimethyl-2,3-dihydro-1H-pyrrolo[2,3-b]pyridine-5-ol
  参考文献：
  名称：

  Simplified bicyclic pyridinol analogues protect mitochondrial function

  摘要：

  Bicyclic pyridinol antioxidants have been reported to suppress the autoxidation of methyl linoleate more effectively than alpha-tocopherol in benzene solution. A few novel lipophilic analogues have recently been synthesized by conjugating a pyridinol core with the phytyl side chain of alpha-tocopherol; these have been shown to possess potent antioxidant activity. However, the complexity of the synthetic routes has hampered their further development. Herein, we describe a facile approach, involving only five synthetic steps, to simplified analogues (1a-1c) and their acetate ester precursors (2a-2c). Simple alkyl chains of different lengths were attached to the 6-methyl group of the antioxidant core via regioselective metalation. These analogues were found to retain biological activity and exhibit protective behaviour under conditions of induced oxidative stress, which could lead to the development of more readily accessible analogues as potential antioxidants capable of preserving mitochondrial function. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2012.03.075

文献信息

• [EN] 1H- PYRROLO [2, 3 -B] PYRIDINE DERIVATIVES AND THEIR USE AS RADICAL QUENCHERS<br/>[FR] DÉRIVÉS 1H-PYRROLO [2,3-B] PYRIDINE ET LEUR UTILISATION COMME AGENTS DE TREMPE DE RADICAUX
  申请人：UNIV ARIZONA

  公开号：WO2013120081A1

  公开（公告）日：2013-08-15

  The present disclosure provides biologically active compounds of formula (I): and pharmaceutically acceptable salts thereof, compositions comprising these compounds, and methods of using these compounds in a variety of applications, such as treatment or suppression of diseases associated with decreased mitochondrial function resulting in diminished ATP production and/or oxidative stress and/or lipid peroxidation.

  本公开提供了化学式（I）的生物活性化合物及其药用盐，包括这些化合物的组合物，以及在各种应用中使用这些化合物的方法，例如治疗或抑制与线粒体功能下降导致ATP产生减少和/或氧化应激和/或脂质过氧化相关的疾病。
• 1H-Pyrrolo [2, 3 -B] Pyridine Derivatives and Their Use as Radical Quenchers
  申请人：Armendariz Guajardo Jose I.

  公开号：US20150011580A1

  公开（公告）日：2015-01-08

  The present disclosure provides biologically active compounds of formula (I): and pharmaceutically acceptable salts thereof, compositions comprising these compounds, and methods of using these compounds in a variety of applications, such as treatment or suppression of diseases associated with decreased mitochondrial function resulting in diminished ATP production and/or oxidative stress and/or lipid peroxidation.

  本公开提供式(I)的生物活性化合物及其药学上可接受的盐，包含这些化合物的组合物，以及使用这些化合物在多种应用中的方法，例如治疗或抑制与减少线粒体功能导致的ATP生产和/或氧化应激和/或脂质过氧化相关的疾病。
• US9440967B2
  申请人：——

  公开号：US9440967B2

  公开（公告）日：2016-09-13
• Simplified bicyclic pyridinol analogues protect mitochondrial function
  作者：Xiaoqing Cai、Omar M. Khdour、Jennifer Jaruvangsanti、Sidney M. Hecht

  DOI：10.1016/j.bmc.2012.03.075

  日期：2012.6

  Bicyclic pyridinol antioxidants have been reported to suppress the autoxidation of methyl linoleate more effectively than alpha-tocopherol in benzene solution. A few novel lipophilic analogues have recently been synthesized by conjugating a pyridinol core with the phytyl side chain of alpha-tocopherol; these have been shown to possess potent antioxidant activity. However, the complexity of the synthetic routes has hampered their further development. Herein, we describe a facile approach, involving only five synthetic steps, to simplified analogues (1a-1c) and their acetate ester precursors (2a-2c). Simple alkyl chains of different lengths were attached to the 6-methyl group of the antioxidant core via regioselective metalation. These analogues were found to retain biological activity and exhibit protective behaviour under conditions of induced oxidative stress, which could lead to the development of more readily accessible analogues as potential antioxidants capable of preserving mitochondrial function. (C) 2012 Elsevier Ltd. All rights reserved.