β-hydroxynaphthaldehyde thiobenzoylhydrazone | 89983-80-2

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: β-hydroxynaphthaldehyde thiobenzoylhydrazone
• 英文别名: N-[(E)-(2-hydroxynaphthalen-1-yl)methylideneamino]benzenecarbothioamide
• CAS: 89983-80-2
• 化学式: C₁₈H₁₄N₂OS
• 分子量: 306.388
• InChiKey: LXCGNHWINHYGJB-XDHOZWIPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.3
• 重原子数：
  22
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  76.7
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  苯硫代甲酰肼 、 2-羟基-1-萘甲醛 以 甲醇 为溶剂， 反应 24.0h， 以70%的产率得到β-hydroxynaphthaldehyde thiobenzoylhydrazone
  参考文献：
  名称：

  Zelenin, K. N.; Alekseev, V. V.; Khrustalev, V. A., Journal of Organic Chemistry USSR (English Translation), 1984, vol. 20, p. 162 - 167

  摘要：

  DOI：

文献信息

• Zelenin, K. N.; Alekseev, V. V.; Khrustalev, V. A., Journal of Organic Chemistry USSR (English Translation), 1984, vol. 20, p. 162 - 167
  作者：Zelenin, K. N.、Alekseev, V. V.、Khrustalev, V. A.、Yakimovich, S. I.、Nikolaev, V. N.、Koshmina, N. V.

  DOI：——

  日期：——
• Design, Synthesis, and Characterization of New Iron Chelators with Anti-Proliferative Activity:  Structure−Activity Relationships of Novel Thiohydrazone Analogues
  作者：Danuta S. Kalinowski、Philip C. Sharpe、Paul V. Bernhardt、Des R. Richardson

  DOI：10.1021/jm070839q

  日期：2007.11.1

  Di-2-pyridylketone isonicotinoyl hydrazone Fe chelators utilize the N,N,O-donor set and have moderate anti-proliferative effects. Their closely related N,N,S-thiosemicarbazone analogues, namely, the di-2pyridylketone thiosemicarbazones, exhibit markedly increased anti-proliferative and redox activity, and this was thought to be due to the inclusion of a sulfur donor atom (Richardson, D. R. et al. J. Med. Chem. 2006, 49, 6510-6521). To further examine the effect of donor atom identity on anti-proliferative activity, we synthesized thiohydrazone analogues of extensively examined aroylhydrazone chelators. The O,N,S-thiohydrazones exhibited decreased anti-proliferative effects compared to their parent aroylhydrazones and reduced redox activity. In contrast, the N,N,S-thiohydrazones showed vastly increased anti-proliferative activity compared to their hydrazone analogues, being comparable to potent thiosemicarbazones. Additionally, N,N,S-thiohydrazone complexes had reversible Fe-III/II couples and exhibited increased redox activity. These observations demonstrate that the N,N,S-donor set is critical for potent anti-proliferative efficacy.