2-(10-hydroxydecyl)-3 methyl-1,4-naphthoquinone

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 2-(10-hydroxydecyl)-3 methyl-1,4-naphthoquinone
• 英文别名: 2-(10-Hydroxydecyl)-3-methylnaphthalene-1,4-dione；2-(10-hydroxydecyl)-3-methylnaphthalene-1,4-dione
• 化学式: C₂₁H₂₈O₃
• 分子量: 328.452
• InChiKey: CASWCSUJRWIELK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.4
• 重原子数：
  24
• 可旋转键数：
  10
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.52
• 拓扑面积：
  54.4
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  11-溴十一酸 在 ammonium peroxydisulfate 、 silver nitrate 、 potassium hydroxide 作用下， 以 水 、 乙腈 为溶剂， 反应 3.0h， 生成 2-(10-hydroxydecyl)-3 methyl-1,4-naphthoquinone
  参考文献：
  名称：

  酰胺连接的氧化还原活性萘醌用于治疗线粒体功能障碍。

  摘要：

  萘醌已被研究作为神经退行性疾病的潜在治疗分子，这主要是基于它们的抗氧化潜力。然而，萘醌衍生物的多效保护作用的理论框架在很大程度上缺失。我们合成了一个新型短链 2,3-二取代萘醌衍生物库，并测量了它们的氧化还原特性，以确定与它们的生物活性的潜在联系。使用具有不同还原潜力的两种细胞系，测试了这些化合物的固有毒性、ATP 水平的急性拯救和细胞保护活性。首次建立了萘醌的构效关系。我们的结果清楚地表明，决定单个化合物的细胞保护程度的是烷基侧链上的基团，而不仅仅是萘醌单元的氧化还原特性或亲脂性。由此，我们开发了许多含有酰胺的萘醌，与临床使用的苯醌艾地苯醌相比，它们在 ATP 拯救和细胞活力模型中具有更高的活性。

  DOI：

  10.1039/c8md00582f

文献信息

• [EN] THERAPEUTIC COMPOUNDS AND METHODS<br/>[FR] COMPOSÉS ET PROCÉDÉS THÉRAPEUTIQUES
  申请人：UNIV TASMANIA

  公开号：WO2018191789A1

  公开（公告）日：2018-10-25

  The invention relates to compounds of Formula (I) and methods for their preparation. Also described are pharmaceutical compositions comprising a compound of Formula (I) and their use in the treatment or prevention of conditions associated with mitochondrial dysfunction. Formula (I)

  该发明涉及式（I）的化合物及其制备方法。还描述了包含式（I）化合物的药物组合物，以及它们在治疗或预防与线粒体功能障碍有关的疾病中的用途。Formula (I)
• Therapeutic compounds and methods
  申请人：UNIVERSITY OF TASMANIA

  公开号：US10934253B2

  公开（公告）日：2021-03-02

  The invention relates to compounds of Formula (I) and methods for their preparation. Also described are pharmaceutical compositions comprising a compound of Formula (I) and their use in the treatment or prevention of conditions associated with mitochondrial dysfunction. Formula (I)

  本发明涉及式（I）化合物及其制备方法。还描述了包含式（I）化合物的药物组合物及其在治疗或预防线粒体功能障碍相关疾病中的用途。式 (I)
• Discovery of Novel 2-Aniline-1,4-naphthoquinones as Potential New Drug Treatment for Leber’s Hereditary Optic Neuropathy (LHON)
  作者：Carmine Varricchio、Kathy Beirne、Pascale Aeschlimann、Charles Heard、Malgorzata Rozanowska、Marcela Votruba、Andrea Brancale

  DOI：10.1021/acs.jmedchem.0c00942

  日期：2020.11.25

  Leber's hereditary optic neuropathy (LHON) is a rare genetic mitochondrial disease and the primary cause of chronic visual impairment for at least 1 in 10 000 individuals in the U.K. Treatment options remain limited, with only a few drug candidates and therapeutic approaches, either approved or in development. Recently, idebenone has been investigated as drug therapy in the treatment of LHON, although evidence for the efficacy of idebenone is limited in the literature. NAD(P)H:quinone oxidoreductase 1 (NQO1) and mitochondrial complex III were identified as the major enzymes involved in idebenone activity. Based on this mode of action, computer-aided techniques and structure-activity relationship (SAR) optimization studies led to the discovery of a series naphthoquinone-related small molecules, with comparable adenosine 5'-triphosphate (ATP) rescue activity to idebenone. Among these, three compounds showed activity in the nanomolar range and one, 2-((4-fluoro-3-(trifluoromethyl)phenyl)amino)-3-(methylthio)naphthalene-1,3-dione (1), demonstrated significantly higher potency ex vivo, and significantly lower cytotoxicity, than idebenone.
• THERAPEUTIC COMPOUNDS AND METHODS
  申请人：UNIVERSITY OF TASMANIA

  公开号：US20200131119A1

  公开（公告）日：2020-04-30

  The invention relates to compounds of Formula (I) and methods for their preparation. Also described are pharmaceutical compositions comprising a compound of Formula (I) and their use in the treatment or prevention of conditions associated with mitochondrial dysfunction. Formula (I)
• KR20220167945A
  申请人：——

  公开号：——

  公开（公告）日：——