5-((5-chloro-2-phenyl-1H-indol-3-yl)methylene)pyrimidine-2,4,6(1H,3H,5H)-trione | 1347738-19-5

• 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-((5-chloro-2-phenyl-1H-indol-3-yl)methylene)pyrimidine-2,4,6(1H,3H,5H)-trione
• 英文别名: 5-[(5-chloro-2-phenyl-1H-indol-3-yl)methylidene]-1,3-diazinane-2,4,6-trione
• CAS: 1347738-19-5
• 化学式: C₁₉H₁₂ClN₃O₃
• 分子量: 365.776
• InChiKey: LNUFTIOTRSQXHM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.24
• 重原子数：
  26.0
• 可旋转键数：
  2.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  91.06
• 氢给体数：
  3.0
• 氢受体数：
  3.0

反应信息

• 作为产物：
  描述：

  巴比妥酸 、 5-chloro-2-phenylindole-3-carboxaldehyde 在 ammonium acetate 作用下， 反应 0.17h， 以88%的产率得到5-((5-chloro-2-phenyl-1H-indol-3-yl)methylene)pyrimidine-2,4,6(1H,3H,5H)-trione
  参考文献：
  名称：

  Solvent-free, microwave assisted Knoevenagel condensation of novel 2,5-disubstituted indole analogues and their biological evaluation

  摘要：

  A rapid, efficient and environmental benign methodology for the preparation of 2,5-disubstituted indole analogues is developed. 2,5-Disubstituted indole-3-carboxaldehydes (1a-c) undergo Knoevenagel condensation with barbiturates (2 & 4), thiazolidine-2,4-dione (6) and 3-methyl-1H-pyrazol-5(4H)-one (8) in solvent-free, NH4OAc catalyzed, microwave assisted reaction. Structures of the products thus obtained were confirmed by their m.p, Elemental analysis, IR. H-1 NMR, C-13 NMR and Mass spectral data. The in vitro antioxidant and cytotoxic activities against three tumor cell lines were evaluated and discussed in terms of their structural differences. Among the screened compounds 9b, 9c, 7b and 5b exhibited excellent antioxidant activity. Compounds 9b, 9c and 7b have shown strong cytotoxicity among the compounds tested. (C) 2011 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2011.10.004

文献信息

• Solvent-free, microwave assisted Knoevenagel condensation of novel 2,5-disubstituted indole analogues and their biological evaluation
  作者：J.S. Biradar、B.S. Sasidhar

  DOI：10.1016/j.ejmech.2011.10.004

  日期：2011.12

  A rapid, efficient and environmental benign methodology for the preparation of 2,5-disubstituted indole analogues is developed. 2,5-Disubstituted indole-3-carboxaldehydes (1a-c) undergo Knoevenagel condensation with barbiturates (2 & 4), thiazolidine-2,4-dione (6) and 3-methyl-1H-pyrazol-5(4H)-one (8) in solvent-free, NH4OAc catalyzed, microwave assisted reaction. Structures of the products thus obtained were confirmed by their m.p, Elemental analysis, IR. H-1 NMR, C-13 NMR and Mass spectral data. The in vitro antioxidant and cytotoxic activities against three tumor cell lines were evaluated and discussed in terms of their structural differences. Among the screened compounds 9b, 9c, 7b and 5b exhibited excellent antioxidant activity. Compounds 9b, 9c and 7b have shown strong cytotoxicity among the compounds tested. (C) 2011 Elsevier Masson SAS. All rights reserved.