2-chloro-3-((2-chlorophenyl)amino)naphthalene-1,4-dione | 21503-30-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 2-chloro-3-((2-chlorophenyl)amino)naphthalene-1,4-dione
• 英文别名: 2-chloro-3-(2-chloro-anilino)-[1,4]naphthoquinone；2-Chlor-3-(2-chlor-anilino)-[1,4]naphthochinon；2-Chloro-3-(2-chloroanilino)naphthalene-1,4-dione；2-chloro-3-(2-chloroanilino)naphthalene-1,4-dione
• CAS: 21503-30-0
• 化学式: C₁₆H₉Cl₂NO₂
• 分子量: 318.159
• InChiKey: ZDGDPOLHZGRBKO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.7
• 重原子数：
  21
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 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 、 邻氯苯胺 在 zinc(II) chloride 作用下， 以 水 为溶剂， 反应 24.0h， 以4%的产率得到2-chloro-3-((2-chlorophenyl)amino)naphthalene-1,4-dione
  参考文献：
  名称：

  Ligand-based design, synthesis and biochemical evaluation of potent and selective inhibitors of Schistosoma mansoni dihydroorotate dehydrogenase

  摘要：

  Schistosomiasis ranks second only to malaria as the most common parasitic disease worldwide. 700 million people are at risk and 240 million are already infected. Praziquantel is the anthelmintic of choice but decreasing efficacy has already been documented. In this work, we exploited the inhibition of Schistosoma mansoni dihydroorotate dehydrogenase (SmDHODH) as a strategy to develop new therapeutics to fight schistosomiasis. A series of quinones (atovaquone derivatives and precursors) was evaluated regarding potency and selectivity against both SmDHODH and human DHODH. The best compound identified is 17 (2-hydroxy-3-isopentylnaphthalene-1,4-dione) with IC50 = 23 +/- 4 nM and selectivity index of 30.83. Some of the new compounds are useful pharmacological tools and represent new lead structures for further optimization. (C) 2019 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2019.02.018