5-([1-(prop-2-yn-1-yl)-1H-indol-3-yl]methylene)pyrimidine-2,4,6(1H,3H,5H)-trione | 1169869-42-4

• 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: 5-([1-(prop-2-yn-1-yl)-1H-indol-3-yl]methylene)pyrimidine-2,4,6(1H,3H,5H)-trione
• 英文别名: 5-{[1-(Prop-2-yn-1-yl)-1h-indol-3-yl]methylene}pyrimidine-2,4,6(1h,3h,5h)trione；5-[(1-prop-2-ynylindol-3-yl)methylidene]-1,3-diazinane-2,4,6-trione
• CAS: 1169869-42-4
• 化学式: C₁₆H₁₁N₃O₃
• 分子量: 293.282
• InChiKey: YMXLNDUVRYSBFE-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.3
• 重原子数：
  22
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.06
• 拓扑面积：
  80.2
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  5-([1-(prop-2-yn-1-yl)-1H-indol-3-yl]methylene)pyrimidine-2,4,6(1H,3H,5H)-trione 、 1-(叠氮甲基)-4-氯苯 在 copper(l) iodide 作用下， 以 四氢呋喃 为溶剂， 反应 12.0h， 以90%的产率得到5-{(1-[(1-{4-chlorobenzyl}-1H-1,2,3-triazol-4-yl)methyl]-1H-indol-3-yl)methylene}pyrimidine-2,4,6(1H,3H,5H)-trione
  参考文献：
  名称：

  Synthesis, Biological Evaluation, and Molecular Docking Studies of Novel 1,2,3-Triazole Tagged 5-[(1H-Indol-3-yl)methylene]pyrimidine-2,4,6(1H,3H,5H)trione Derivatives

  摘要：

  Novel 5-{(1-[(1-phenyl-1H-1,2,3-triazol-4-yl)methyl]-1H-indol-3-yl)methylene}pyrimidine-2,4,6-(1H,3H,5H)trione derivatives (5a-5k) were synthesized by the click reaction. All compounds 5a-5k were characterized by H-1 and C-13 NMR, IR and Mass spectra and evaluated for their in vitro anticancer activity against cervical cancer cell lines. Among all, compound 5e (IC50 = 6.76 mu M), shown high inhibitory activity. Docking analysis of all the compounds with the Lipid kinase PI3K-alpha revealed that the compound 5e fitted well in the active site pocket, showing the best docking score (LibDock) of 123.274.

  DOI：

  10.1134/s1070363218030313
• 作为产物：
  描述：

  3-吲哚甲醛 在 哌啶 、 potassium carbonate 作用下， 以 乙醇 、 N,N-二甲基甲酰胺 为溶剂， 反应 6.0h， 生成 5-([1-(prop-2-yn-1-yl)-1H-indol-3-yl]methylene)pyrimidine-2,4,6(1H,3H,5H)-trione
  参考文献：
  名称：

  Synthesis, Biological Evaluation, and Molecular Docking Studies of Novel 1,2,3-Triazole Tagged 5-[(1H-Indol-3-yl)methylene]pyrimidine-2,4,6(1H,3H,5H)trione Derivatives

  摘要：

  Novel 5-{(1-[(1-phenyl-1H-1,2,3-triazol-4-yl)methyl]-1H-indol-3-yl)methylene}pyrimidine-2,4,6-(1H,3H,5H)trione derivatives (5a-5k) were synthesized by the click reaction. All compounds 5a-5k were characterized by H-1 and C-13 NMR, IR and Mass spectra and evaluated for their in vitro anticancer activity against cervical cancer cell lines. Among all, compound 5e (IC50 = 6.76 mu M), shown high inhibitory activity. Docking analysis of all the compounds with the Lipid kinase PI3K-alpha revealed that the compound 5e fitted well in the active site pocket, showing the best docking score (LibDock) of 123.274.

  DOI：

  10.1134/s1070363218030313

文献信息

• Design, synthesis and anticancer activities of hybrids of indole and barbituric acids—Identification of highly promising leads
  作者：Palwinder Singh、Matinder Kaur、Pooja Verma

  DOI：10.1016/j.bmcl.2009.04.014

  日期：2009.6

  By combining the structural features of indole and barbituric acid, new hybrid molecules were designed and synthesized. Evaluations of these molecules over 60 cell line panel of human cancer cells have identified two molecules with significant anticancer activities. Dockings of two active molecules in the active sites of COX-2, thymidylate synthase and ribonucleotide reductase indicate their strong interactions with these enzymes. (C) 2009 Elsevier Ltd. All rights reserved.