(11E)-N'-(5-hydroxy-2-methyl-1-oxonaphthalen-4(1H)-ylidene)acetohydrazide

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: (11E)-N'-(5-hydroxy-2-methyl-1-oxonaphthalen-4(1H)-ylidene)acetohydrazide
• 化学式: C₁₃H₁₂N₂O₃
• 分子量: 244.25
• InChiKey: PDWJYLDXNJWSGT-XNTDXEJSSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.38
• 重原子数：
  18.0
• 可旋转键数：
  1.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.15
• 拓扑面积：
  78.76
• 氢给体数：
  2.0
• 氢受体数：
  4.0

反应信息

• 作为产物：
  描述：

  兰雪醌 、 乙酰肼 在 三氟乙酸 作用下， 以 甲醇 为溶剂， 以68%的产率得到(11E)-N'-(5-hydroxy-2-methyl-1-oxonaphthalen-4(1H)-ylidene)acetohydrazide
  参考文献：
  名称：

  Anticancer phytochemical analogs 37: Synthesis, characterization, molecular docking and cytotoxicity of novel plumbagin hydrazones against breast cancer cells

  摘要：

  We have synthesized, structurally characterized and examined cytotoxicity of novel plumbagin hydrazones against estrogen and progesterone receptor positive (ER+/PR+) MCF-7 and triple negative MDA-MB-231 breast cancer cell lines in order to evaluate the potential of these novel phytochemical analogs. Compounds were docked into the protein cavity of p50-subunit of NF-kappa B protein revealing better fit and better binding energies than the parent plumbagin compound. This was also reflected in their superior cytotoxicities which were found to be mediated by inhibition of NF-kappa B expression. These compounds can provide a starting point for the development of novel drug molecules against triple negative breast cancers. (C) 2014 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2014.04.100

文献信息

• Anticancer phytochemical analogs 37: Synthesis, characterization, molecular docking and cytotoxicity of novel plumbagin hydrazones against breast cancer cells
  作者：Prasad Dandawate、Aamir Ahmad、Jyoti Deshpande、K. Venkateswara Swamy、Ejazuddin M. Khan、Madhukar Khetmalas、Subhash Padhye、Fazlul Sarkar

  DOI：10.1016/j.bmcl.2014.04.100

  日期：2014.7

  We have synthesized, structurally characterized and examined cytotoxicity of novel plumbagin hydrazones against estrogen and progesterone receptor positive (ER+/PR+) MCF-7 and triple negative MDA-MB-231 breast cancer cell lines in order to evaluate the potential of these novel phytochemical analogs. Compounds were docked into the protein cavity of p50-subunit of NF-kappa B protein revealing better fit and better binding energies than the parent plumbagin compound. This was also reflected in their superior cytotoxicities which were found to be mediated by inhibition of NF-kappa B expression. These compounds can provide a starting point for the development of novel drug molecules against triple negative breast cancers. (C) 2014 Elsevier Ltd. All rights reserved.