3-chloro-2-[5-(N,N-dimethylhydrazono)fur-2-yl]-1,4-naphthoquinone | 1016168-11-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 3-chloro-2-[5-(N,N-dimethylhydrazono)fur-2-yl]-1,4-naphthoquinone
• 英文别名: 2-chloro-3-[5-[(dimethylhydrazinylidene)methyl]furan-2-yl]naphthalene-1,4-dione
• CAS: 1016168-11-8
• 化学式: C₁₇H₁₃ClN₂O₃
• 分子量: 328.755
• InChiKey: ULTOXHCLLHRPSY-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  23.0
• 可旋转键数：
  3.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  62.88
• 氢给体数：
  0.0
• 氢受体数：
  5.0

反应信息

• 作为产物：
  描述：

  2-糠醛 2,2-二甲基腙 、 2-氯-1,4-萘醌 在 溶剂黄146 作用下， 反应 8.0h， 以77%的产率得到3-chloro-2-[5-(N,N-dimethylhydrazono)fur-2-yl]-1,4-naphthoquinone
  参考文献：
  名称：

  Studies on quinones. Part 42: Synthesis of furylquinone and hydroquinones with antiproliferative activity against human tumor cell lines

  摘要：

  The preparation of furyl-1,4-quinone and hydroquinones by reaction of 2-furaldehyde N,N-dimethylhydrazone with benzo- and naphthoquinones is reported. Access to furylnaphthoquinones from unactivated quinones requires acid-induced conditions, however oxidative coupling reactions of activated quinones proceed under neutral conditions. The in vitro cytotoxic activity of the prepared compounds against a panel of three human cancer cell lines has been studied. Most of the furyl-1,4-quinones exhibited good antiproliferative activity (GI(50) = 6.5-33.5 mu m) against the MCF-7, NCI-H460, and SF-268 (CNS cancer) cell lines chosen for testing. (C) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2007.10.028