N-[4-[[4-[二(2-氯乙基)氨基]苯基]甲基]苯基]喹啉-4-胺盐酸盐 | 133041-54-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 中文名称: N-[4-[[4-[二(2-氯乙基)氨基]苯基]甲基]苯基]喹啉-4-胺盐酸盐
• 英文名称: N-[4-[[4-[bis(2-chloroethyl)amino]phenyl]methyl]phenyl]quinolin-4-amine;hydron;chloride
• CAS: 133041-54-0
• 化学式: C₂₆H₂₅Cl₂N₃*ClH
• 分子量: 486.872
• InChiKey: RLFGZCRMNDFORQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.28
• 重原子数：
  32
• 可旋转键数：
  9
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.19
• 拓扑面积：
  28.2
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  N-[4-[[4-[二(2-氯乙基)氨基]苯基]甲基]苯基]喹啉-4-胺盐酸盐 、 三氟甲烷磺酸甲酯 以 苯 为溶剂， 反应 24.0h， 生成 N-[4-[[4-[bis(2-chloroethyl)amino]phenyl]methyl]phenyl]-1-methylquinolin-1-ium-4-amine;trifluoromethanesulfonate
  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：

  4-[[4-[Bis(2-chloroethyl)amino]phenyl]methyl]aniline 、 4-氯喹啉 、 盐酸 以75%的产率得到
  参考文献：
  名称：

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

  摘要：

  DOI：

文献信息

• O'Connor, Charmian J.; Denny, William A.; Fan, Jun-Yao, Journal of the Chemical Society. Perkin transactions II, 1991, # 12, p. 1933 - 1940
  作者：O'Connor, Charmian J.、Denny, William A.、Fan, Jun-Yao、Gravatt, G. Lance、Grigor, Bruce A.、McLennan, Duncan J.

  DOI：——

  日期：——
• 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：——
• DNA-directed alkylating agents. 4. 4-Anilinoquinoline-based minor groove directed aniline mustards
  作者：G. Lance Gravatt、Bruce C. Baguley、William R. Wilson、William A. Denny

  DOI：10.1021/jm00109a005

  日期：1991.5

  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.