2-chloro-3-((4-propylphenyl)amino)naphthalene-1,4-dione | 64505-72-2

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 2-chloro-3-((4-propylphenyl)amino)naphthalene-1,4-dione
• 英文别名: 2-chloro-3-(4-propyl-anilino)-[1,4]naphthoquinone；2-Chlor-3-(4-propyl-anilino)-[1,4]naphthochinon；2-Chloro-3-(4-propylanilino)naphthalene-1,4-dione
• CAS: 64505-72-2
• 化学式: C₁₉H₁₆ClNO₂
• 分子量: 325.795
• InChiKey: GRZNTFFZRSWMJS-UHFFFAOYSA-N

物化性质

• 沸点：
  442.3±45.0 °C(Predicted)
• 密度：
  1.29±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.5
• 重原子数：
  23
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.16
• 拓扑面积：
  46.2
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  2,3-二氯-1,4-萘醌 、 对丙基苯胺 以 乙醇 为溶剂， 以38%的产率得到2-chloro-3-((4-propylphenyl)amino)naphthalene-1,4-dione
  参考文献：
  名称：

  Discovery of Novel 2-Aniline-1,4-naphthoquinones as Potential New Drug Treatment for Leber’s Hereditary Optic Neuropathy (LHON)

  摘要：

  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.

  DOI：

  10.1021/acs.jmedchem.0c00942