2-hydroxy-5-(dipropylaminomethyl)acetophenone

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2-hydroxy-5-(dipropylaminomethyl)acetophenone
• 英文别名: 1-[5-[(Dipropylamino)methyl]-2-hydroxyphenyl]ethanone；1-[5-[(dipropylamino)methyl]-2-hydroxyphenyl]ethanone
• 化学式: C₁₅H₂₃NO₂
• 分子量: 249.353
• InChiKey: INOGBZKBTYXINJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  18
• 可旋转键数：
  7
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.53
• 拓扑面积：
  40.5
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  2-羟基-5-氯甲基苯乙酮 、 二正丙胺 在 potassium carbonate 作用下， 以 氯仿 为溶剂， 反应 20.0h， 以94%的产率得到2-hydroxy-5-(dipropylaminomethyl)acetophenone
  参考文献：
  名称：

  Cytotoxicity effects of transition-metal chelators of the 5-substituted 2-hydroxyacetophenones and their oximes

  摘要：

  A series of 5-substituted 2-hydroxyacetophenones (A) and their oxime derivatives (B) were synthesized, and their cytotoxic activities towards MCF-7 breast cancer cells and B-16 melanoma cells were compared. The substitution on the benzylic position enabled variation of the lipophilic nature of the compound, while the chelating site remained free for metal binding. The results obtained indicate that the lipophilic properties of the compounds are favorable for cytotoxicity activity and that the oximes which are lipophilic enough (eg, B-4, B-5, B-9) are more potent than the corresponding ketones (A-4, A-5, A-9). All the potent oximes examined in this work showed strong cardiotoxicity.

  DOI：

  10.1016/0223-5234(96)88269-9

文献信息

• Cytotoxicity effects of transition-metal chelators of the 5-substituted 2-hydroxyacetophenones and their oximes
  作者：A Warshawsky、N Kahana、E Beery、G Kessler-Icekson、A Novogrodsky、J Nordenberg

  DOI：10.1016/0223-5234(96)88269-9

  日期：1995.1

  A series of 5-substituted 2-hydroxyacetophenones (A) and their oxime derivatives (B) were synthesized, and their cytotoxic activities towards MCF-7 breast cancer cells and B-16 melanoma cells were compared. The substitution on the benzylic position enabled variation of the lipophilic nature of the compound, while the chelating site remained free for metal binding. The results obtained indicate that the lipophilic properties of the compounds are favorable for cytotoxicity activity and that the oximes which are lipophilic enough (eg, B-4, B-5, B-9) are more potent than the corresponding ketones (A-4, A-5, A-9). All the potent oximes examined in this work showed strong cardiotoxicity.