N1-(7-chloroquinolin-4-yl)-N2-(naphthalen-2-ylmethyl)ethane-1,2-diamine | 1259500-62-3

• 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: N1-(7-chloroquinolin-4-yl)-N2-(naphthalen-2-ylmethyl)ethane-1,2-diamine
• 英文别名: N'-(7-chloroquinolin-4-yl)-N-(naphthalen-2-ylmethyl)ethane-1,2-diamine
• CAS: 1259500-62-3
• 化学式: C₂₂H₂₀ClN₃
• 分子量: 361.874
• InChiKey: MWLKKSMXZYIZEO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.1
• 重原子数：
  26
• 可旋转键数：
  6
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.14
• 拓扑面积：
  37
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  在 sodium tetrahydroborate 、 水 作用下， 以 甲醇 为溶剂， 反应 2.0h， 生成 N1-(7-chloroquinolin-4-yl)-N2-(naphthalen-2-ylmethyl)ethane-1,2-diamine
  参考文献：
  名称：

  Synthesis and antimalarial activities of rhenium bioorganometallics based on the 4-aminoquinoline structure

  摘要：

  A bioorganometallic approach to malaria therapy led to the discovery of ferroquine (FQ, SSR97193). To assess the importance of the electronic properties of the ferrocenyl group, cyclopentadienyltricarbonylrhenium analogues related to FQ, were synthesized. The reaction of [N-(7-chloro-4-quinolinyl)-1,2-ethanodiamine] with the cyrhetrenylaldehyde complexes (eta(5)-C5H4CHO)Re(CO)(3) and [eta(5)-1,2-C5H3(CH2OH) (CHO)]Re(CO)(3) produces the corresponding imine derivatives [eta(5)-1,2-C5H3(R)(CH=N-CH2CH2NH-QN)]Re(CO)(3) R = H 3a; R = CH2OH 3b; QN = N-(7-Cl-4-quinolinyl). Reduction of 3a and 3b with sodium borohydride in methanol yields quantitatively the amine complexes [eta(5)-1,2-C5H3(R)(CH2-NH-CH2CH2NH-QN)]Re(CO)(3) R = H 4a; R = CH2OH 4b. To establish the role of the cyrethrenyl moiety in the antimalarial activity of this series, purely organic parent compounds were also synthesized and tested. Evaluation of antimalarial activity measured in vitro against the CQ-resistant strains (W2) and the CQ-susceptible strain (3D7) of Plasmodium falciparum indicates that these cyrhetrene conjugates are less active compared to their ferrocene and organic analogues. These data suggest an original mode-of-action of FQ and ferrocenyl analogues in relationship with the redox pharmacophore. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2010.09.005