5-naphthalen-2-yl-1H-pyrazol-3-carboxylic acid (2-hydroxynaphthalen-1-ylmethylene)-hydrazide | 1259484-85-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 5-naphthalen-2-yl-1H-pyrazol-3-carboxylic acid (2-hydroxynaphthalen-1-ylmethylene)-hydrazide
• 英文别名: SKI-I；N-[(2-hydroxynaphthalen-1-yl)methylideneamino]-3-naphthalen-2-yl-1H-pyrazole-5-carboxamide
• CAS: 1259484-85-9；306301-68-8
• 化学式: C₂₅H₁₈N₄O₂
• mdl: MFCD01654927
• 分子量: 406.444
• InChiKey: XOXCTLAKMCIWCF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.3
• 重原子数：
  31
• 可旋转键数：
  4
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  90.4
• 氢给体数：
  3
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  5-naphthalen-2-yl-1H-pyrazol-3-carboxylic acid hydrazide 、 2-羟基-1-萘甲醛 在 溶剂黄146 作用下， 以 二甲基亚砜 为溶剂， 以94%的产率得到5-naphthalen-2-yl-1H-pyrazol-3-carboxylic acid (2-hydroxynaphthalen-1-ylmethylene)-hydrazide
  参考文献：
  名称：

  Synthesis and bioactivity of sphingosine kinase inhibitors and their novel aspirinyl conjugated analogs

  摘要：

  Sphingosine kinase (SphK) is a lipid kinase with oncogenic activity, and SphK inhibitors (SKIS) are known for their anti-cancer activity. Here, we report highly efficient syntheses of SKIs and their aspirinyl (Asp) analogs. Both SKIs and their Asp analogs were highly cytotoxic towards multiple human cancer cell lines: in several cases the Asp analogs were up to three times more effective. Furthermore, they were equally potent inhibitors of SphK. The pharmacokinetic study indicated that SKI-I-Asp cleaved efficiently to form SKI-I and the half-life of SKI-I was increased from similar to 7 h in SKI-I to similar to 10 h in SKI-I-Asp injected mice, thereby prolonging its effect. In summary, the Asp-conjugated SKIs seem to be promising prodrugs of SKIs where delivery in vivo remains a problem. (C) 2010 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2010.06.005