1-[4-(5-Hydroxy-4-oxo-2-phenylchromen-7-yl)oxybutyl]indole-3-carbaldehyde | 1529772-97-1

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 黄酮类化合物
• 英文名称: 1-[4-(5-Hydroxy-4-oxo-2-phenylchromen-7-yl)oxybutyl]indole-3-carbaldehyde
• 英文别名: 1-[4-(5-hydroxy-4-oxo-2-phenylchromen-7-yl)oxybutyl]indole-3-carbaldehyde
• CAS: 1529772-97-1
• 化学式: C₂₈H₂₃NO₅
• 分子量: 453.494
• InChiKey: RWPNKCRRZMYZHC-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.2
• 重原子数：
  34
• 可旋转键数：
  8
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.14
• 拓扑面积：
  77.8
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  1-(2,6-二氯苯基)-1,3-二氢-2H-吲哚-2-酮 、 1-[4-(5-Hydroxy-4-oxo-2-phenylchromen-7-yl)oxybutyl]indole-3-carbaldehyde 以67%的产率得到1-(2,6-dichlorophenyl)-3-{1-[4-(5-hydroxy-4-oxo-2-phenyl-4H-chromen-7-yloxy)butyl]-1H-indol-3-ylmethylene}-1,3-dihydro-indol-2-one
  参考文献：
  名称：

  Rationally designed hybrid molecules with appreciable COX-2 inhibitory and anti-nociceptive activities

  摘要：

  Six molecules were obtained by the combination of three biologically and medicinally significant moieties- indole, chrysin and pyrazole. Bio-evaluation of these hybrid molecules showed significant inhibition of COX-2 enzymatic activity over that of COX-1 and appreciable anti-nociceptive activity, checked at swiss albino mice. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2013.11.080
• 作为产物：
  描述：

  3-吲哚甲醛 在 sodium hydride 、 potassium carbonate 作用下， 以 N,N-二甲基甲酰胺 、 丙酮 为溶剂， 反应 3.0h， 生成 1-[4-(5-Hydroxy-4-oxo-2-phenylchromen-7-yl)oxybutyl]indole-3-carbaldehyde
  参考文献：
  名称：

  Triblock Conjugates: Identification of a Highly Potent Antiinflammatory Agent

  摘要：

  Rationally designed conjugates of chrysin, indole, and barbituric acid were synthesized and screened for their antiinflammatory activities through in vitro and in vivo experiments. Improved over the previously reported chrysin indole pyrazole conjugates and also in comparison to the chrysin, indole, and barbituric acid based COX-2 inhibitors, the new compounds have displayed significantly better IC50 for COX-2 and some of them also exhibited inhibition of 5-LOX enzyme. For one of the test compounds, IC50 for COX-2 and 5-LOX was 1 and 1.5 nM, respectively. Investigations of Swiss Albino mice through capsaicin induced paw lickings and dextran induced inflammation showed that these compounds possess appreciable analgesic and antiinflammatory activities. K-i, K-a, and Delta G for the enzyme compound interaction were calculated and found to be in agreement with The experimental results were supported by the molecular docking studies of the compounds in the active site of COX-2 and 5-LOX. Overall, a highly promising antiinflammatory agent was identified. the biological data.

  DOI：

  10.1021/acs.jmedchem.5b00952