8-chloro-N-[3-[4-[3-[(8-chloropyrrolo[1,2-a]quinoxalin-4-yl)amino]propyl]piperazin-1-yl]propyl]pyrrolo[1,2-a]quinoxalin-4-amine

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二氮杂萘
• 英文名称: 8-chloro-N-[3-[4-[3-[(8-chloropyrrolo[1,2-a]quinoxalin-4-yl)amino]propyl]piperazin-1-yl]propyl]pyrrolo[1,2-a]quinoxalin-4-amine
• 化学式: C₃₂H₃₄Cl₂N₈
• 分子量: 601.582
• InChiKey: CKUOLWWDHLNWEF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.9
• 重原子数：
  42
• 可旋转键数：
  10
• 环数：
  7.0
• sp3杂化的碳原子比例：
  0.31
• 拓扑面积：
  65.1
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  1-(5-chloro-2-nitrophenyl)-1H-pyrrole 在 bismuth(III) chloride 、 sodium tetrahydroborate 、 potassium carbonate 、 三氯氧磷 作用下， 以 乙醇 、 N,N-二甲基甲酰胺 、 甲苯 为溶剂， 反应 14.0h， 生成 8-chloro-N-[3-[4-[3-[(8-chloropyrrolo[1,2-a]quinoxalin-4-yl)amino]propyl]piperazin-1-yl]propyl]pyrrolo[1,2-a]quinoxalin-4-amine
  参考文献：
  名称：

  Synthesis, Antimalarial Activity, and Molecular Modeling of New Pyrrolo[1,2-a]quinoxalines, Bispyrrolo[1,2-a]quinoxalines, Bispyrido[3,2-e]pyrrolo[1,2-a]pyrazines, and Bispyrrolo[1,2-a]thieno[3,2-e]pyrazines

  摘要：

  Three pyrrolo[1,2-a]quinoxalines, 15 bispyrrolo[1,2-a]quinoxalines, bispyrido[3,2-e]pyrrolo[1,2-a]pyrazines, and bispyrrolo[1,2-a]thieno[3,2-e]pyrazines were synthesized from various substituted nitroanilines or nitropyridines and tested for their in vitro activity upon the erythrocytic development of Plasmodium falciparum strains with different chloroquine-resistance status. Bispyrrolo[1,2-a]quinoxalines showed superior antimalarial. activity with respect to monopyrrolo[1,2-a]quinoxalines. The best activity was observed with bispyrrolo[1,2-a]quinoxalines linked by a bis(3-aminopropyl)piperazine. Moreover, it was observed that the presence of a methoxy group on the pyrrolo[1,2-a]quinoxaline nucleus increased the pharmacological activity. Drug effects upon beta-hematin formation were assayed and showed similar or higher inhibitory activities than CQ. A possible mechanism of interaction implicating binding of pyrroloquinoxalines to beta-hematin was supported by molecular modeling.

  DOI：

  10.1021/jm0310840

文献信息

• Synthesis, Antimalarial Activity, and Molecular Modeling of New Pyrrolo[1,2-<i>a</i>]quinoxalines, Bispyrrolo[1,2-<i>a</i>]quinoxalines, Bispyrido[3,2-<i>e</i>]pyrrolo[1,2-<i>a</i>]pyrazines, and Bispyrrolo[1,2-<i>a</i>]thieno[3,2-<i>e</i>]pyrazines
  作者：Jean Guillon、Philippe Grellier、Mehdi Labaied、Pascal Sonnet、Jean-Michel Léger、Rébecca Déprez-Poulain、Isabelle Forfar-Bares、Patrick Dallemagne、Nicolas Lemaître、Fabienne Péhourcq、Jacques Rochette、Christian Sergheraert、Christian Jarry

  DOI：10.1021/jm0310840

  日期：2004.4.1

  Three pyrrolo[1,2-a]quinoxalines, 15 bispyrrolo[1,2-a]quinoxalines, bispyrido[3,2-e]pyrrolo[1,2-a]pyrazines, and bispyrrolo[1,2-a]thieno[3,2-e]pyrazines were synthesized from various substituted nitroanilines or nitropyridines and tested for their in vitro activity upon the erythrocytic development of Plasmodium falciparum strains with different chloroquine-resistance status. Bispyrrolo[1,2-a]quinoxalines showed superior antimalarial. activity with respect to monopyrrolo[1,2-a]quinoxalines. The best activity was observed with bispyrrolo[1,2-a]quinoxalines linked by a bis(3-aminopropyl)piperazine. Moreover, it was observed that the presence of a methoxy group on the pyrrolo[1,2-a]quinoxaline nucleus increased the pharmacological activity. Drug effects upon beta-hematin formation were assayed and showed similar or higher inhibitory activities than CQ. A possible mechanism of interaction implicating binding of pyrroloquinoxalines to beta-hematin was supported by molecular modeling.