1,2-Ethanediamine, N,N-diethyl-N'-[7-(trifluoromethyl)-4-quinolinyl]- | 169815-49-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 喹啉及其衍生物
• 英文名称: 1,2-Ethanediamine, N,N-diethyl-N'-[7-(trifluoromethyl)-4-quinolinyl]-
• 英文别名: N',N'-diethyl-N-[7-(trifluoromethyl)quinolin-4-yl]ethane-1,2-diamine
• CAS: 169815-49-0
• 化学式: C₁₆H₂₀F₃N₃
• 分子量: 311.35
• InChiKey: NVSLNNKQKJTRQW-UHFFFAOYSA-N

物化性质

• 沸点：
  403.6±45.0 °C(Predicted)
• 密度：
  1.199±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  22
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.44
• 拓扑面积：
  28.2
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  7-（三氯甲基）-4-羟基喹啉 在 三氯氧磷 作用下， 反应 10.17h， 生成 1,2-Ethanediamine, N,N-diethyl-N'-[7-(trifluoromethyl)-4-quinolinyl]-
  参考文献：
  名称：

  Structure−Activity Relationships for Antiplasmodial Activity among 7-Substituted 4-Aminoquinolines

  摘要：

  Aminoquinolines (AQs) with diaminoalkane side chains (-HNRNEt2) shorter or longer than the isopentyl side chain [-HNCHMe(CH2)(3)NEt2] of chloroquine are active against both chloroquine-susceptible and -resistant Plasmodium falciparum. (De, D.; et al. Am. J. Trop. Med. Hyg. 1996, 55, 579-583). In the studies reported here, we examined structure-activity relationships (SARs) among AQs with different N,N-diethyldiaminoalkane side chains and different substituents at the 7-position occupied by Cl in chloroquine. 7-Iodo- and 7-bromo-AQs with diaminoalkane side chains [-HN(CH2)(2)NEt2, -HN(CH2)(3)NEt2, or -HNCHMeCH2NEt2] were as active as the corresponding 7-chloro-AQs against both chloroquine-susceptible and -resistant P. falciparum (IC(50)s of 3-12 nM). In contrast, with one exception, 7-fluoro-AQs and 7-trifluoromethyl-AQs were less active against chloroquine-susceptible P. falciparum (IC(50)s of 15-50 nM) and substantially less active against chloroquine-resistant P. falciparum (IC(50)s of 18-500 nM). Furthermore, most 7-OMe-AQs were inactive against both chloroquine-susceptible (IC(50)s of 17-150 nM) and -resistant P. falciparum (IC(50)s of 90-3000 nM).

  DOI：

  10.1021/jm980146x

文献信息

• Structure−Activity Relationships for Antiplasmodial Activity among 7-Substituted 4-Aminoquinolines
  作者：Dibyendu De、Frances M. Krogstad、Larry D. Byers、Donald J. Krogstad

  DOI：10.1021/jm980146x

  日期：1998.12.1

  Aminoquinolines (AQs) with diaminoalkane side chains (-HNRNEt2) shorter or longer than the isopentyl side chain [-HNCHMe(CH2)(3)NEt2] of chloroquine are active against both chloroquine-susceptible and -resistant Plasmodium falciparum. (De, D.; et al. Am. J. Trop. Med. Hyg. 1996, 55, 579-583). In the studies reported here, we examined structure-activity relationships (SARs) among AQs with different N,N-diethyldiaminoalkane side chains and different substituents at the 7-position occupied by Cl in chloroquine. 7-Iodo- and 7-bromo-AQs with diaminoalkane side chains [-HN(CH2)(2)NEt2, -HN(CH2)(3)NEt2, or -HNCHMeCH2NEt2] were as active as the corresponding 7-chloro-AQs against both chloroquine-susceptible and -resistant P. falciparum (IC(50)s of 3-12 nM). In contrast, with one exception, 7-fluoro-AQs and 7-trifluoromethyl-AQs were less active against chloroquine-susceptible P. falciparum (IC(50)s of 15-50 nM) and substantially less active against chloroquine-resistant P. falciparum (IC(50)s of 18-500 nM). Furthermore, most 7-OMe-AQs were inactive against both chloroquine-susceptible (IC(50)s of 17-150 nM) and -resistant P. falciparum (IC(50)s of 90-3000 nM).