2-(15-triphenylphosphoniumpentadecyl)-3-methyl-5,6-dimethoxy-1,4-benzoquinone bromide | 764723-92-4

• 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: 2-(15-triphenylphosphoniumpentadecyl)-3-methyl-5,6-dimethoxy-1,4-benzoquinone bromide
• 英文别名: mitoQ15；[15-(4,5-dimethoxy-2-methyl-3,6-dioxo-1,4-cyclohexadien-1-yl)pentadecyl]triphenylphosphonium bromide；15-(4,5-Dimethoxy-2-methyl-3,6-dioxocyclohexa-1,4-dien-1-yl)pentadecyl-triphenylphosphanium;bromide
• CAS: 764723-92-4
• 化学式: Br*C₄₂H₅₄O₄P
• 分子量: 733.766
• InChiKey: GHBDUYFAHXXHFY-UHFFFAOYSA-M

计算性质

• 辛醇/水分配系数(LogP)：
  6.42
• 重原子数：
  48
• 可旋转键数：
  21
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.43
• 拓扑面积：
  52.6
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  、 三苯基膦 在 乙醇 、 水 、 甲醇 、 palladium 10% on activated carbon 、 氧气 作用下， 反应 72.0h， 以55%的产率得到2-(15-triphenylphosphoniumpentadecyl)-3-methyl-5,6-dimethoxy-1,4-benzoquinone bromide
  参考文献：
  名称：

  Synthesis and characterization of mitoQ and idebenone analogues as mediators of oxygen consumption in mitochondria

  摘要：

  Analogues of mitoQ and idebenone were synthesized to define the structural elements that support oxygen consumption in the mitochondrial respiratory chain. Eight analogues were prepared and fully characterized, then evaluated for their ability to support oxygen consumption in the mitochondrial respiratory chain. While oxygen consumption was strongly inhibited by mitoQ analogues 2-4 in a chain length-dependent manner, modification of idebenone by replacement of the quinone methoxy groups by methyl groups (analogues 6-8) reduced, but did not eliminate, oxygen consumption. Idebenone analogues 6-8 also displayed significant cytoprotective properties toward cultured mammalian cells in which glutathione had been depleted by treatment with diethyl maleate. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2010.06.104

文献信息

• [EN] MITOQUINONE DERIVATIVES USED AS MITOCHONDRIALLY TARGETED ANTIOXIDANTS<br/>[FR] DERIVES DE LA MITOQUINONE UTILISES EN TANT QU'ANTIOXYDANTS CIBLES DE MANIERE MITOCHONDRIALE
  申请人：ANTIPODEAN BIOTECHNOLOGY LTD

  公开号：WO2005019232A1

  公开（公告）日：2005-03-03

  This invention relates to pharmaceutically acceptable amphiphilic antioxidant compounds, compositions and dosage forms comprising said compounds, and methods and uses reliant on said compounds.The exemplified compounds are all mitoquinone derivatives, being methoxyphenyl alkyl triphenylphosphonium or methoxy dioxocyclohexadiene alkyl triphenylphosphonium derivatives. The compounds, compositions, dosage forms, uses and methods are useful in, for example, the treatment of diseases or conditions associated with oxidative stress.

  这项发明涉及药用可接受的两性抗氧化剂化合物，包括含有该化合物的组合物和剂型，以及依赖于该化合物的方法和用途。所示化合物均为丁醌衍生物，为甲氧基苯基烷基三苯基膦盐或甲氧基二氧环己二烯烷基三苯基膦盐衍生物。这些化合物、组合物、剂型、用途和方法在治疗与氧化应激相关的疾病或症状方面是有用的。
• MITOQUINONE DERIVATIVES USED AS MITOCHONDRIALLY TARGETED ANTIOXIDANTS
  申请人：Taylor Kenneth Martin

  公开号：US20110288055A1

  公开（公告）日：2011-11-24

  This invention relates to pharmaceutically acceptable amphiphilic antioxidant compounds, compositions and dosage forms comprising said compounds, and methods and uses reliant on said compounds. The exemplified compounds are all mitoquinone derivatives, being methoxyphenyl alkyl triphenylphosphonium or methoxy dioxocyclohexadiene alkyl triphenylphosphonium derivatives. The compounds, compositions, dosage forms, uses and methods are useful in, for example, the treatment of diseases or conditions associated with oxidative stress.

  本发明涉及药用可接受的亲水亲脂性抗氧化剂化合物，包括该化合物的组合物和剂型，以及依赖于该化合物的方法和用途。其中所示的化合物均为丝氨酸醌衍生物，包括甲氧基苯基烷基三苯基膦或甲氧基二氧代环己二烯烷基三苯基膦衍生物。该化合物、组合物、剂型、用途和方法可用于例如治疗与氧化应激相关的疾病或症状。
• US7888335B2
  申请人：——

  公开号：US7888335B2

  公开（公告）日：2011-02-15
• US7888334B2
  申请人：——

  公开号：US7888334B2

  公开（公告）日：2011-02-15