(11E)-2-hydroxy-N'-(5-hydroxy-2-methyl-1-oxonaphthalen-4(1H)-ylidene)benzohydrazide | 1374305-47-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: (11E)-2-hydroxy-N'-(5-hydroxy-2-methyl-1-oxonaphthalen-4(1H)-ylidene)benzohydrazide
• CAS: 1374305-47-1
• 化学式: C₁₈H₁₄N₂O₄
• 分子量: 322.32
• InChiKey: ZVFYCQYNIJUZQZ-CPNJWEJPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.37
• 重原子数：
  24.0
• 可旋转键数：
  2.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.06
• 拓扑面积：
  98.99
• 氢给体数：
  3.0
• 氢受体数：
  5.0

反应信息

• 作为产物：
  描述：

  兰雪醌 、 水杨酰肼 在 三氟乙酸 作用下， 以 甲醇 为溶剂， 反应 4.0h， 以66%的产率得到(11E)-2-hydroxy-N'-(5-hydroxy-2-methyl-1-oxonaphthalen-4(1H)-ylidene)benzohydrazide
  参考文献：
  名称：

  Synthesis, characterization, molecular docking and cytotoxic activity of novel plumbagin hydrazones against breast cancer cells

  摘要：

  Novel plumbagin hydrazonates were prepared, structurally characterized and evaluated for anti-proliferative activity against estrogen receptor-positive MCF-7 and triple negative MDA-MB-231 and MDA-MB-468 breast cancer cell lines which exhibited superior inhibitory activity than parent plumbagin compound. Molecular docking studies indicated that hydroxyl groups on plumbagin and hydrazonate side chain favor additional hydrogen bonding interactions with amino acid residues in p50-subunit of NF-kappa B protein and these compounds inhibited NF-kappa B expression which may be responsible for the enhanced anti-proliferative activity. These compounds were found to be more effective against triple negative breast cancer cells and might serve as a starting point for building future strategies against triple negative breast cancers which are known for their increased drug resistance and poor prognosis of breast cancer patients. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2012.03.060

文献信息

• Synthesis, characterization, molecular docking and cytotoxic activity of novel plumbagin hydrazones against breast cancer cells
  作者：Prasad Dandawate、Ejazuddin Khan、Subhash Padhye、Himanshi Gaba、Swati Sinha、Jyoti Deshpande、K. Venkateswara Swamy、Madhukar Khetmalas、Aamir Ahmad、Fazlul H. Sarkar

  DOI：10.1016/j.bmcl.2012.03.060

  日期：2012.5

  Novel plumbagin hydrazonates were prepared, structurally characterized and evaluated for anti-proliferative activity against estrogen receptor-positive MCF-7 and triple negative MDA-MB-231 and MDA-MB-468 breast cancer cell lines which exhibited superior inhibitory activity than parent plumbagin compound. Molecular docking studies indicated that hydroxyl groups on plumbagin and hydrazonate side chain favor additional hydrogen bonding interactions with amino acid residues in p50-subunit of NF-kappa B protein and these compounds inhibited NF-kappa B expression which may be responsible for the enhanced anti-proliferative activity. These compounds were found to be more effective against triple negative breast cancer cells and might serve as a starting point for building future strategies against triple negative breast cancers which are known for their increased drug resistance and poor prognosis of breast cancer patients. (C) 2012 Elsevier Ltd. All rights reserved.