4'acetamidophenyl 4-phenyl ether | 133041-69-7

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 4'acetamidophenyl 4-phenyl ether
• 英文别名: N-[4-[4-[bis(2-hydroxyethyl)amino]phenoxy]phenyl]acetamide
• CAS: 133041-69-7
• 化学式: C₁₈H₂₂N₂O₄
• 分子量: 330.384
• InChiKey: ZNEMWPMGOCLUSQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.23
• 重原子数：
  24.0
• 可旋转键数：
  8.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.28
• 拓扑面积：
  82.03
• 氢给体数：
  3.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  4'acetamidophenyl 4-phenyl ether 在 盐酸 、 三乙胺 、 sodium chloride 作用下， 以 甲醇 、 水 、 N,N-二甲基甲酰胺 、 苯 为溶剂， 反应 43.0h， 生成 Quinolinium, 4-((4-(4-(bis(2-chloroethyl)amino)phenoxy)phenyl)amino)-1-methyl-, salt with trifluoromethanesulfonic acid (1:1)
  参考文献：
  名称：

  DNA-directed alkylating agents. 4. 4-Anilinoquinoline-based minor groove directed aniline mustards

  摘要：

  A series of 4-anilinoquinoline-linked aniline mustards of widely varying mustard reactivity were prepared and evaluated for their antitumor activity. The compounds were designed as minor groove binding agents, where the aniline mustard ring is itself part of the DNA-binding ligand. While there was a general trend for cytotoxicity to correlate with mustard reactivity, this was much less pronounced than with untargeted mustards. The compounds were much more cytotoxic than the parent diols, and were at least 10-fold more cytotoxic than the corresponding aniline mustards themselves. Comparative cell line studies suggested that the mechanism of cytotoxicity varied with mustard reactivity. The most reactive mustards cross-linked DNA, while cell killing by the less reactive compounds appeared to be by the formation of bulky monoadducts. The compounds were active but not particularly dose-potent against P388 leukemia in vivo. The modest potency may be related to their poor aqueous solubility, since the more soluble methyl quaternary salts were equally active at much lower doses.

  DOI：

  10.1021/jm00109a005
• 作为产物：
  描述：

  对乙酰氨基酚 在 palladium on activated charcoal sodium hydroxide 、 氢气 、 溶剂黄146 作用下， 以 甲醇 为溶剂， 反应 25.5h， 生成 4'acetamidophenyl 4-phenyl ether
  参考文献：
  名称：

  DNA-directed alkylating agents. 4. 4-Anilinoquinoline-based minor groove directed aniline mustards

  摘要：

  A series of 4-anilinoquinoline-linked aniline mustards of widely varying mustard reactivity were prepared and evaluated for their antitumor activity. The compounds were designed as minor groove binding agents, where the aniline mustard ring is itself part of the DNA-binding ligand. While there was a general trend for cytotoxicity to correlate with mustard reactivity, this was much less pronounced than with untargeted mustards. The compounds were much more cytotoxic than the parent diols, and were at least 10-fold more cytotoxic than the corresponding aniline mustards themselves. Comparative cell line studies suggested that the mechanism of cytotoxicity varied with mustard reactivity. The most reactive mustards cross-linked DNA, while cell killing by the less reactive compounds appeared to be by the formation of bulky monoadducts. The compounds were active but not particularly dose-potent against P388 leukemia in vivo. The modest potency may be related to their poor aqueous solubility, since the more soluble methyl quaternary salts were equally active at much lower doses.

  DOI：

  10.1021/jm00109a005

文献信息

• GRAVATT, G. LANCE;BAGULEY, BRUCE C.;WILSON, WILLIAM R.;DENNY, WILLIAM A., J. MED. CHEM., 34,(1991) N, C. 1552-1560
  作者：GRAVATT, G. LANCE、BAGULEY, BRUCE C.、WILSON, WILLIAM R.、DENNY, WILLIAM A.

  DOI：——

  日期：——