(2E,5E)-2,5-bis(isoquinolin-5-ylmethylene)cyclopentanone

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 异喹啉及其衍生物
• 英文名称: (2E,5E)-2,5-bis(isoquinolin-5-ylmethylene)cyclopentanone
• 英文别名: (2E,5E)-2,5-bis(isoquinolin-5-ylmethylidene)cyclopentan-1-one
• 化学式: C₂₅H₁₈N₂O
• 分子量: 362.431
• InChiKey: BRBMTEYZYVZFJD-IWGRKNQJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.9
• 重原子数：
  28
• 可旋转键数：
  2
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.08
• 拓扑面积：
  42.8
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  异喹啉-5-甲醛 、 环戊酮 在 sodium hydroxide 作用下， 以 乙醇 为溶剂， 以87%的产率得到(2E,5E)-2,5-bis(isoquinolin-5-ylmethylene)cyclopentanone
  参考文献：
  名称：

  Synthesis and evaluation of the antiparasitic activity of bis-(arylmethylidene) cycloalkanones

  摘要：

  A series of bis-(arylmethylidene)-cycloalkanones was synthesized by cross-aldol condensation. The activity of the compounds was evaluated against amastigotes forms of Trypanosoma cruzi and promastigotes forms of Leishmania amazonensis. The cytotoxicity of the active compounds on uninfected fibroblasts or macrophages was established in vitro to evaluate the selectivity of their antiparasitic effects. Six compounds displayed trypanocidal activity against amastigotes intracellular forms of T. cruzi with IC50 values ranging from 7.0 to 249 mu M. Besides these six compounds, eight other molecules exhibited significant leishmanicidal activity (IC50 values ranging from 0.6 to 110.4 mu M). Two compounds can be considered as promising antiparasitic lead molecules because they showed IC50 values in the low-micromolar range (<= 1.2 mu M) with an adequate SI (>= 19.9). To understand the mechanism of action of these compounds, two possible molecular targets were investigated: trypanothione reductase (TR) and cruzain. (C) 2013 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2013.11.011

文献信息

• Synthesis and evaluation of the antiparasitic activity of bis-(arylmethylidene) cycloalkanones
  作者：Saulo F.P. Braga、Érika V.P. Alves、Rafaela S. Ferreira、Jordana R.B. Fradico、Paula S. Lage、Mariana C. Duarte、Tatiana G. Ribeiro、Policarpo A.S. Júnior、Alvaro J. Romanha、Maiko L. Tonini、Mário Steindel、Eduardo F. Coelho、Renata B. de Oliveira

  DOI：10.1016/j.ejmech.2013.11.011

  日期：2014.1

  A series of bis-(arylmethylidene)-cycloalkanones was synthesized by cross-aldol condensation. The activity of the compounds was evaluated against amastigotes forms of Trypanosoma cruzi and promastigotes forms of Leishmania amazonensis. The cytotoxicity of the active compounds on uninfected fibroblasts or macrophages was established in vitro to evaluate the selectivity of their antiparasitic effects. Six compounds displayed trypanocidal activity against amastigotes intracellular forms of T. cruzi with IC50 values ranging from 7.0 to 249 mu M. Besides these six compounds, eight other molecules exhibited significant leishmanicidal activity (IC50 values ranging from 0.6 to 110.4 mu M). Two compounds can be considered as promising antiparasitic lead molecules because they showed IC50 values in the low-micromolar range (<= 1.2 mu M) with an adequate SI (>= 19.9). To understand the mechanism of action of these compounds, two possible molecular targets were investigated: trypanothione reductase (TR) and cruzain. (C) 2013 Elsevier Masson SAS. All rights reserved.