5-Bromo-pentanoic acid 3-(7-chloro-quinolin-4-ylamino)-5-(2-piperidin-1-yl-acetylamino)-benzyl ester | 362054-31-7

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: 5-Bromo-pentanoic acid 3-(7-chloro-quinolin-4-ylamino)-5-(2-piperidin-1-yl-acetylamino)-benzyl ester
• 英文别名: [3-[(7-Chloroquinolin-4-yl)amino]-5-[(2-piperidin-1-ylacetyl)amino]phenyl]methyl 5-bromopentanoate
• CAS: 362054-31-7
• 化学式: C₂₈H₃₂BrClN₄O₃
• 分子量: 587.944
• InChiKey: HQBPUCBZHPJVBQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.5
• 重原子数：
  37
• 可旋转键数：
  12
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.39
• 拓扑面积：
  83.6
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  哌啶 、 5-Bromo-pentanoic acid 3-(7-chloro-quinolin-4-ylamino)-5-(2-piperidin-1-yl-acetylamino)-benzyl ester 在 N-乙基哌啶 作用下， 反应 18.0h， 以110 mg的产率得到[3-[(7-Chloroquinolin-4-yl)amino]-5-[(2-piperidin-1-ylacetyl)amino]phenyl]methyl 5-piperidin-1-ylpentanoate
  参考文献：
  名称：

  Synthesis and in Vitro and in Vivo Antimalarial Activity of New 4-Anilinoquinolines

  摘要：

  A new series of 4-anilinoquinolines with two proton-accepting side chains has been synthesized. Antimalarial activity and levels of cytotoxicity upon both MRC-5 cells and macrophages were found to be highly dependent upon the features of these side chains. Several compounds were found to be active in the low nanomolar range, against both chloroquine-sensitive and -resistant strains of Plasmodium falciparum in vitro. From among them, a morpholino derivative cured mice infected by Plasmodium berghei and displayed a lower toxicity than amodiaquine upon mouse macrophages.

  DOI：

  10.1021/jm010842o
• 作为产物：
  描述：

  4,7-二氯喹啉 在 N-乙基哌啶 、 N-甲基吗啉 、 4-二甲氨基吡啶 、 N,N'-二环己基碳二亚胺 、 bromo-tris(1-pyrrolidinyl)phosphonium hexafluorophosphate 作用下， 以 乙醇 、 二氯甲烷 、 氯仿 、 N,N-二甲基甲酰胺 为溶剂， 反应 109.0h， 生成 5-Bromo-pentanoic acid 3-(7-chloro-quinolin-4-ylamino)-5-(2-piperidin-1-yl-acetylamino)-benzyl ester
  参考文献：
  名称：

  Synthesis and in Vitro and in Vivo Antimalarial Activity of New 4-Anilinoquinolines

  摘要：

  A new series of 4-anilinoquinolines with two proton-accepting side chains has been synthesized. Antimalarial activity and levels of cytotoxicity upon both MRC-5 cells and macrophages were found to be highly dependent upon the features of these side chains. Several compounds were found to be active in the low nanomolar range, against both chloroquine-sensitive and -resistant strains of Plasmodium falciparum in vitro. From among them, a morpholino derivative cured mice infected by Plasmodium berghei and displayed a lower toxicity than amodiaquine upon mouse macrophages.

  DOI：

  10.1021/jm010842o

文献信息

• Synthesis and in Vitro and in Vivo Antimalarial Activity of New 4-Anilinoquinolines
  作者：Sandrine Delarue、Sophie Girault、Louis Maes、Marie-Ange Debreu-Fontaine、Mehdi Labaeïd、Philippe Grellier、Christian Sergheraert

  DOI：10.1021/jm010842o

  日期：2001.8.1

  A new series of 4-anilinoquinolines with two proton-accepting side chains has been synthesized. Antimalarial activity and levels of cytotoxicity upon both MRC-5 cells and macrophages were found to be highly dependent upon the features of these side chains. Several compounds were found to be active in the low nanomolar range, against both chloroquine-sensitive and -resistant strains of Plasmodium falciparum in vitro. From among them, a morpholino derivative cured mice infected by Plasmodium berghei and displayed a lower toxicity than amodiaquine upon mouse macrophages.