1-(2-(7-chloroquinolin-4-ylamino)hexyl)-N-cyclohexyl-2-methyl-6-oxopiperidine-2-carboxamide

• 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: 1-(2-(7-chloroquinolin-4-ylamino)hexyl)-N-cyclohexyl-2-methyl-6-oxopiperidine-2-carboxamide
• 英文别名: 1-[6-[(7-chloroquinolin-4-yl)amino]hexyl]-N-cyclohexyl-2-methyl-6-oxopiperidine-2-carboxamide
• 化学式: C₂₈H₃₉ClN₄O₂
• 分子量: 499.096
• InChiKey: PJUGWZZUPSKPIR-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.5
• 重原子数：
  35
• 可旋转键数：
  10
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.61
• 拓扑面积：
  74.3
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  1,6-己二胺 以 甲醇 为溶剂， 反应 22.5h， 生成 1-(2-(7-chloroquinolin-4-ylamino)hexyl)-N-cyclohexyl-2-methyl-6-oxopiperidine-2-carboxamide
  参考文献：
  名称：

  Application of multicomponent reactions to antimalarial drug discovery. Part 2: New antiplasmodial and antitrypanosomal 4-aminoquinoline γ- and δ-lactams via a ‘catch and release’ protocol

  摘要：

  A parallel synthesis of a new series of 4-aminoquinoline gamma- and delta-lactams synthesized via the Ugi 3-component 4-centre multicomponent reaction is described. The basicity of the quinoline nitrogen was exploited in the purification of compounds via a 'catch and release' protocol. Yields ranging from 60% to 77% and purities as high as 96% were obtained. Compound 29, the most active against a chloroquine-resistant W2 strain of Plasmodium falciparum with an IC50 of 0.096 mu M, also inhibited recombinant falcipain-2 in vitro (IC50 = 17.6 mu M). Compound 17 inhibited the growth of Trypanosoma brucei with an ED50 of 1.44 mu M whilst exhibiting a favourable therapeutic index of 409 against a human KB cell line. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2006.04.035

文献信息

• Application of multicomponent reactions to antimalarial drug discovery. Part 2: New antiplasmodial and antitrypanosomal 4-aminoquinoline γ- and δ-lactams via a ‘catch and release’ protocol
  作者：Chitalu C. Musonda、Jiri Gut、Philip J. Rosenthal、Vanessa Yardley、Renata C. Carvalho de Souza、Kelly Chibale

  DOI：10.1016/j.bmc.2006.04.035

  日期：2006.8

  A parallel synthesis of a new series of 4-aminoquinoline gamma- and delta-lactams synthesized via the Ugi 3-component 4-centre multicomponent reaction is described. The basicity of the quinoline nitrogen was exploited in the purification of compounds via a 'catch and release' protocol. Yields ranging from 60% to 77% and purities as high as 96% were obtained. Compound 29, the most active against a chloroquine-resistant W2 strain of Plasmodium falciparum with an IC50 of 0.096 mu M, also inhibited recombinant falcipain-2 in vitro (IC50 = 17.6 mu M). Compound 17 inhibited the growth of Trypanosoma brucei with an ED50 of 1.44 mu M whilst exhibiting a favourable therapeutic index of 409 against a human KB cell line. (c) 2006 Elsevier Ltd. All rights reserved.