4-((3R,7R,11R)-3-benzoxy-3,7,11,15-tetramethylhexadec-1-ynyl)-2,3-dihydro-1,6-dimethyl-1H-pyrrolo[2,3-b]pyridin-5-yl acetate | 1257984-24-9

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 异戊烯醇脂质
• 英文名称: 4-((3R,7R,11R)-3-benzoxy-3,7,11,15-tetramethylhexadec-1-ynyl)-2,3-dihydro-1,6-dimethyl-1H-pyrrolo[2,3-b]pyridin-5-yl acetate
• 英文别名: [1,6-dimethyl-4-[(3R,7R,11R)-3,7,11,15-tetramethyl-3-phenylmethoxyhexadec-1-ynyl]-2,3-dihydropyrrolo[2,3-b]pyridin-5-yl] acetate
• CAS: 1257984-24-9
• 化学式: C₃₈H₅₆N₂O₃
• 分子量: 588.874
• InChiKey: YSPADPLZJOYGKX-QQJQPJPWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  10.7
• 重原子数：
  43
• 可旋转键数：
  19
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.63
• 拓扑面积：
  51.7
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  4-((3R,7R,11R)-3-benzoxy-3,7,11,15-tetramethylhexadec-1-ynyl)-2,3-dihydro-1,6-dimethyl-1H-pyrrolo[2,3-b]pyridin-5-yl acetate 在 20 % Pd(OH)2/C 、 氢气 作用下， 以 甲醇 为溶剂， 反应 18.0h， 以71%的产率得到1,6-dimethyl-4-((3R,7R,11R)-3-hydroxy-3,7,11,15-tetramethylhexadecyl)-2,3-dihydro-1H-pyrrolo[2,3-b]pyridin-5-yl acetate
  参考文献：
  名称：

  Design, synthesis, and evaluation of an α-tocopherol analogue as a mitochondrial antioxidant

  摘要：

  An efficient synthesis has provided access to a novel alpha-tocopherol analogue (2), as well as its trifluoroacetate salt and acetate ester. An annulation reaction was used to establish the pyridinol core structure and a Stille coupling reaction was employed for conjugation with the tocopherol side chain. This analogue was shown to suppress the levels of reactive oxygen species in cultured cells, and to quench peroxidation of mitochondrial membranes. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2010.08.030
• 作为产物：
  描述：

  4-((3R,7R,11R)-3-benzoxy-3,7,11,15-tetramethylhexadec-1-ynyl)-1,6-dimethyl-2,3-dihydro-1H-pyrrolo[2,3-b]pyridin-5-yl formate 、 乙酸酐 在 二异丁基氢化铝 、 4-二甲氨基吡啶 、 三乙胺 作用下， 以 二氯甲烷 、 甲苯 为溶剂， 反应 25.5h， 以78%的产率得到4-((3R,7R,11R)-3-benzoxy-3,7,11,15-tetramethylhexadec-1-ynyl)-2,3-dihydro-1,6-dimethyl-1H-pyrrolo[2,3-b]pyridin-5-yl acetate
  参考文献：
  名称：

  Design, synthesis, and evaluation of an α-tocopherol analogue as a mitochondrial antioxidant

  摘要：

  An efficient synthesis has provided access to a novel alpha-tocopherol analogue (2), as well as its trifluoroacetate salt and acetate ester. An annulation reaction was used to establish the pyridinol core structure and a Stille coupling reaction was employed for conjugation with the tocopherol side chain. This analogue was shown to suppress the levels of reactive oxygen species in cultured cells, and to quench peroxidation of mitochondrial membranes. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2010.08.030

文献信息

• Multifunctional Radical Quenchers and Their Uses
  申请人：HECHT Sidney

  公开号：US20130267546A1

  公开（公告）日：2013-10-10

  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相关的疾病，导致ATP产生减少和/或氧化应激和/或脂质过氧化。
• MULTIFUNCTIONAL RADICAL QUENCHERS AND THEIR USE
  申请人：Arizona Board Of Regents

  公开号：EP2536690B1

  公开（公告）日：2018-08-08
• US8952025B2
  申请人：——

  公开号：US8952025B2

  公开（公告）日：2015-02-10