N,N-diethyl-N'-(7-iodoquinolin-4-yl)ethane-1,2-diamine | 72249-77-5

• 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: N,N-diethyl-N'-(7-iodoquinolin-4-yl)ethane-1,2-diamine
• 英文别名: 1,2-Ethanediamine, N,N-diethyl-N'-(7-iodo-4-quinolinyl)-；N',N'-diethyl-N-(7-iodoquinolin-4-yl)ethane-1,2-diamine
• CAS: 72249-77-5
• 化学式: C₁₅H₂₀IN₃
• 分子量: 369.248
• InChiKey: JTPCORSQUAFUJH-UHFFFAOYSA-N

物化性质

• 沸点：
  457.7±40.0 °C(Predicted)
• 密度：
  1.488±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  19
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  28.2
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  ethyl 7-iodo-4-oxo-1,4-dihydroquinoline-3-carboxylate 在 sodium hydroxide 、 三氯氧磷 作用下， 以 二苯醚 为溶剂， 反应 11.17h， 生成 N,N-diethyl-N'-(7-iodoquinolin-4-yl)ethane-1,2-diamine
  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

• Antimalarial Quinolines and Methods of Use Thereof
  申请人：Wolf Christian

  公开号：US20110045100A1

  公开（公告）日：2011-02-24

  One aspect of the invention relates to substitute quinolines with antimalarial activity, and compositions and kits comprising at least one of them. Another aspect of the invention relates to methods for the treatment or prevention or both of malaria comprising administering to a subject a therapeutically effective amount of such a compound. Importantly, a number of the compounds show excellent potency against both chloroquine-sensitive and chloroquine-resistant strains.

  本发明的一个方面涉及具有抗疟活性的替代喹啉，以及包含至少其中之一的组合物和试剂盒。另一个方面涉及用这种化合物向受试者施用治疗有效量的方法，以治疗或预防疟疾。重要的是，其中一些化合物对氯喹敏感和氯喹耐药菌株都表现出极高的效力。
• 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).