(1R,2R)-N1-(7-chloroquinolein-4-yl)cyclohexane-1,2-diamine

• 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: (1R,2R)-N1-(7-chloroquinolein-4-yl)cyclohexane-1,2-diamine
• 英文别名: (1R,2R)-2-N-(7-chloroquinolin-4-yl)cyclohexane-1,2-diamine
• 化学式: C₁₅H₁₈ClN₃
• 分子量: 275.781
• InChiKey: FLFRSWXQLFLIPI-TZMCWYRMSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  19
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  50.9
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  二茂铁甲醛 、 (1R,2R)-N1-(7-chloroquinolein-4-yl)cyclohexane-1,2-diamine 在 sodium tetrahydroborate 作用下， 以 甲醇 为溶剂， 反应 5.5h， 以95%的产率得到(1R,2R)-N1-(7-chloroquinolin-4-yl)-N2-(ferrocenylmethyl)cyclohexane-1,2-diamine
  参考文献：
  名称：

  Synthesis and in vitro antiplasmodial activity of ferrocenyl aminoquinoline derivatives

  摘要：

  The aim of this study was to synthesize a series of ferrocenyl 4-aminoquinolines and to evaluate their activities against Plasmodium falciparum F32 (chloroquine-sensitive) and FCB1 and K1 (chloroquino-resistant). Some of the ferrocenyl compounds exhibited in vitro antiplasmodial activity in the nM range. In particular, (1R,4R)-N1-(7-chloroquinolin-4-yl)-N4-(ferrocenylmethyl)-N4-methylcyclohexane-1,4-diamine 17 presented the lowest IC50 value (26 nM) against CQ-resistant strains. (C) 2014 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2014.11.065
• 作为产物：
  描述：

  4,7-二氯喹啉 、 (1R,2R)-1,2-diaminocyclohexane 反应 4.0h， 以90%的产率得到(1R,2R)-N1-(7-chloroquinolein-4-yl)cyclohexane-1,2-diamine
  参考文献：
  名称：

  Synthesis and in vitro antiplasmodial activity of ferrocenyl aminoquinoline derivatives

  摘要：

  The aim of this study was to synthesize a series of ferrocenyl 4-aminoquinolines and to evaluate their activities against Plasmodium falciparum F32 (chloroquine-sensitive) and FCB1 and K1 (chloroquino-resistant). Some of the ferrocenyl compounds exhibited in vitro antiplasmodial activity in the nM range. In particular, (1R,4R)-N1-(7-chloroquinolin-4-yl)-N4-(ferrocenylmethyl)-N4-methylcyclohexane-1,4-diamine 17 presented the lowest IC50 value (26 nM) against CQ-resistant strains. (C) 2014 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2014.11.065

文献信息

• An Exploration of the Structure-activity Relationships of 4−Aminoquinolines: Novel Antimalarials with Activity In-vivo
  作者：F M D Ismail、M J DAscombe、P CArr、S E NOrth

  DOI：10.1111/j.2042-7158.1996.tb03985.x

  日期：2011.4.12

  The structure-activity relationships of bisquinolines, a potentially important group of novel antimalarial drugs, were studied. The high-temperature (180-250 degrees C) synthesis of 4-aminoquinolines, including bisquinolines, by nucleophilic displacement was both fast and efficient Several bisquinolines including (+/-)-trans-N1,N2-bis(7-trifluoroquinolin-4-yl)cyclohexane-1, 2-diamine and 1R,2R-(-)-

  研究了潜在的重要的新型抗疟药组双喹啉的构效关系。通过亲核取代反应，高温（180-250摄氏度）合成4-氨基喹啉，包括双喹啉既快速又有效。几种双喹啉包括（+/-）-反-N1，N2-双（7-三氟喹啉-4） -基）环己烷-1，2-二胺和1R，2R-（-）-，1S，2S-（+）-，（+/-）-反式和顺式N1，N2-双（7-氯喹啉- 4-基）环己烷-1，2-二胺对小鼠的伯氏疟原虫表现出有效的活性。（+/-）-反式-N1，N2-双（7-氯喹啉-4-基）环己烷-1，2-二胺具有口服活性。我们的结果表明，这些化合物符合喹啉抗疟药的假定受体。此外，在4位上通过杂环桥连接的7-卤代喹啉，
• Synthesis and in vitro antiplasmodial activity of ferrocenyl aminoquinoline derivatives
  作者：Gabin Mwande Maguene、Jean-Bernard Lekana-Douki、Elisabeth Mouray、Till Bousquet、Philippe Grellier、Sylvain Pellegrini、Fousseyni Samba Toure Ndouo、Jacques Lebibi、Lydie Pélinski

  DOI：10.1016/j.ejmech.2014.11.065

  日期：2015.1

  The aim of this study was to synthesize a series of ferrocenyl 4-aminoquinolines and to evaluate their activities against Plasmodium falciparum F32 (chloroquine-sensitive) and FCB1 and K1 (chloroquino-resistant). Some of the ferrocenyl compounds exhibited in vitro antiplasmodial activity in the nM range. In particular, (1R,4R)-N1-(7-chloroquinolin-4-yl)-N4-(ferrocenylmethyl)-N4-methylcyclohexane-1,4-diamine 17 presented the lowest IC50 value (26 nM) against CQ-resistant strains. (C) 2014 Elsevier Masson SAS. All rights reserved.