2-(15-hydroxypentadecyl)-3-methyl-5,6-dimethoxy-1,4-benzoquinone | 764723-91-3

• 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-hydroxypentadecyl)-3-methyl-5,6-dimethoxy-1,4-benzoquinone
• 英文别名: 2-(15-hydroxypentadecyl)-5,6-dimethoxy-3-methyl-[1,4]benzoquinone；2-(15-Hydroxypentadecyl)-5,6-dimethoxy-3-methylcyclohexa-2,5-diene-1,4-dione
• CAS: 764723-91-3
• 化学式: C₂₄H₄₀O₅
• 分子量: 408.579
• InChiKey: VEYVSIPRUUTYIT-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7
• 重原子数：
  29
• 可旋转键数：
  17
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.75
• 拓扑面积：
  72.8
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  2-(15-hydroxypentadecyl)-3-methyl-5,6-dimethoxy-1,4-benzoquinone 在 4-二甲氨基吡啶 、 三乙胺 、 sodium bromide 作用下， 以 二氯甲烷 、 丙酮 为溶剂， 反应 7.5h， 生成 2-(15-bromopentadecyl)-3-methyl-5,6-dimethoxy-1,4-benzoquinone
  参考文献：
  名称：

  Biological evaluation of new mimetics of annonaceous acetogenins: Alteration of right scaffold by click linkage with aromatic functionalities

  摘要：

  A small library of analogues of annonaceous acetogenins through click linkage with aromatic moieties is established using a convergent modular fragment-assembly approach. These analogues exhibited low micromolar inhibitory activities against the proliferation of several human cancer cell lines. Structure-activity relationship (SAR) of these analogues indicates that replacement of the methoxy groups of ubiquinone ring with methyl groups is proved to be a useful strategy for improving the anticancer activity of quinone-acetogenin hybrids. (C) 2014 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2014.03.062
• 作为产物：
  描述：

  2,3-二甲氧基-5-甲基-1,4-苯醌 、 16-羟基棕榈酸 在 dipotassium peroxodisulfate 、 silver nitrate 作用下， 以 水 、 乙腈 为溶剂， 反应 0.5h， 以33%的产率得到2-(15-hydroxypentadecyl)-3-methyl-5,6-dimethoxy-1,4-benzoquinone
  参考文献：
  名称：

  [EN] MITOQUINONE DERIVATIVES USED AS MITOCHONDRIALLY TARGETED ANTIOXIDANTS
  [FR] DERIVES DE LA MITOQUINONE UTILISES EN TANT QU'ANTIOXYDANTS CIBLES DE MANIERE MITOCHONDRIALE

  摘要：

  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。

  公开号：

  WO2005019232A1

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 Martin Kenneth

  公开号：US20060229278A1

  公开（公告）日：2006-10-12

  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 compounds, compositions, dosage forms, uses and methods are useful in, for example, the treatment of diseases or conditions associated with oxidative stress.

  本发明涉及到药学上可接受的两性亲水抗氧化化合物，包括含有该化合物的组合物和剂量形式，以及依赖于该化合物的方法和用途。该化合物、组合物、剂量形式、用途和方法可用于例如治疗与氧化应激相关的疾病或病况。
• Mitoquinone Derivatives Used as Mitochondrially Targeted Antioxidants
  申请人：Murphy Patrick Michael

  公开号：US20070238709A1

  公开（公告）日：2007-10-11

  This invention relates to methods to screen for, identify, select and synthesise amphiphilic mitochondrially targeted antioxidant compounds, and compositions, dosage forms and methods 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 and methods are useful in, for example, the treatment of diseases or conditions associated with oxidative stress.

  本发明涉及筛选、鉴定、选择和合成两性亲和力线粒体靶向抗氧化剂化合物的方法，以及依赖于该化合物的组合物、剂型和方法。所示化合物均为线粒体喹酮衍生物，为甲氧基苯基烷基三苯基膦或甲氧基二氧杂环己二烯烷基三苯基膦衍生物。该化合物、组合物、剂型和方法可用于治疗与氧化应激相关的疾病或病状。
• 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。
• Synthesis and characterization of mitoQ and idebenone analogues as mediators of oxygen consumption in mitochondria
  作者：Damien Y. Duveau、Pablo M. Arce、Robert A. Schoenfeld、Nidhi Raghav、Gino A. Cortopassi、Sidney M. Hecht

  DOI：10.1016/j.bmc.2010.06.104

  日期：2010.9

  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.