2-[1-(4-chlorobenzoyl)-5-methoxy-2-methylindol-3-yl]-N-pyrimidin-2-ylacetamide | 819079-99-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吲哚及其衍生物
• 英文名称: 2-[1-(4-chlorobenzoyl)-5-methoxy-2-methylindol-3-yl]-N-pyrimidin-2-ylacetamide
• CAS: 819079-99-7
• 化学式: C₂₃H₁₉ClN₄O₃
• 分子量: 434.882
• InChiKey: CTWFRONXKZNKMT-UHFFFAOYSA-N

物化性质

• 熔点：
  167 °C(Solv: ethanol (64-17-5))
• 密度：
  1.35±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.2
• 重原子数：
  31
• 可旋转键数：
  5
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.13
• 拓扑面积：
  86.1
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  1,3,5-三嗪-2,4,6-三胺,N,N'''-1,2-乙二基二[N-[3-[[4,6-二[丁基(2,2,6,6-四甲基-4-哌啶基)氨基]-1,3,5-三嗪-2-基]氨基]丙基]-N,N''-二丁基-N,N''-二(2,2,6,6-四甲基-4-哌啶基)- 、 吲哚美辛 在 4-二甲氨基吡啶 、 N,N'-二环己基碳二亚胺 作用下， 以 二氯甲烷 为溶剂， 反应 5.0h， 以16%的产率得到2-[1-(4-chlorobenzoyl)-5-methoxy-2-methylindol-3-yl]-N-pyrimidin-2-ylacetamide
  参考文献：
  名称：

  Indomethacin Amides as a Novel Molecular Scaffold for Targeting Trypanosoma cruzi Sterol 14α-Demethylase

  摘要：

  Trypanosoma cruzi (TC) causes Chagas disease, which in its chronic stage remains incurable. We have shown recently that specific inhibition of TC sterol 14 alpha-demethylase (TCCYP51) with imidazole derivatives is effective in killing both extracellular and intracellular human stages of TC: An alternative set of TCCYP51 inhibitors has been identified using optical high throughput screening followed by web-database search for similar structures. The best TCCYP51 inhibitor from this search was found to have structural similarity to a class of cyclooxygenase-2-selective inhibitors, the indomethacin-amides. A number of indomethacin-amides were found to bind to TCCYP51, inhibit its activity in vitro, and produce strong antiparasitic effects in the cultured TC cells. Analysis of TC sterol composition indicated that the mode of action of the compounds is by inhibition of sterol biosynthesis in the parasite.

  DOI：

  10.1021/jm801643b