1-(2'-hydroxy-4'-methoxyphenyl)-3-(1-indol-3-yl)-prop-2-en-1-one | 33268-86-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 酚类
• 英文名称: 1-(2'-hydroxy-4'-methoxyphenyl)-3-(1-indol-3-yl)-prop-2-en-1-one
• 英文别名: 1-(2'-hydroxy-4'-methoxyphenyl)-3-(1H-indol-3-yl)-2-propen-1-one；1-(2-hydroxy-4-methoxy-phenyl)-3-indol-3-yl-propenone；1-(2-hydroxy-4-methoxyphenyl)-3-(1H-indol-3-yl)prop-2-en-1-one
• CAS: 33268-86-9
• 化学式: C₁₈H₁₅NO₃
• 分子量: 293.322
• InChiKey: FBEVRNKVAMTEHP-UHFFFAOYSA-N

物化性质

• 沸点：
  569.2±50.0 °C(predicted)
• 密度：
  1.305±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4
• 重原子数：
  22
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.06
• 拓扑面积：
  62.3
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  3-吲哚甲醛 、 丹皮酚 在 哌啶 作用下， 以 乙醇 为溶剂， 以25.6%的产率得到1-(2'-hydroxy-4'-methoxyphenyl)-3-(1-indol-3-yl)-prop-2-en-1-one
  参考文献：
  名称：

  哌啶介导的正杂环查耳酮的合成及其抗菌活性

  摘要：

  查耳酮1-（2'-羟基-芳基）-3-（1-吲哚-3-基）-丙-2-烯-1-一（3）和1-（2'-羟基-芳基）-3 -（2-氯喹啉-3-基）-丙-2-烯-1-酮（6）是通过哌啶介导的乙醇溶液缩合而合成的。邻羟基苯 乙酮（1）与相应的杂芳基-3-甲醛。该结构是根据元素（C，H，N）分析，UV，IR， 1 H NMR光谱数据建立的。化合物 和 筛选了针对多种细菌制剂的抗菌活性。J.杂环化​​学.2010。

  DOI：

  10.1002/jhet.268

文献信息

• Photogeneration of reactive oxygen species and photoinduced plasmid DNA cleavage by novel synthetic chalcones
  作者：Y. Yesuthangam、S. Pandian、K. Venkatesan、R. Gandhidasan、R. Murugesan

  DOI：10.1016/j.jphotobiol.2010.12.004

  日期：2011.3

  This paper describes the synthesis and photodynamic properties of six different chalcone derivatives. Using N,N-dimethyl-4-nitrosoaniline (RNO) bleaching assay, the singlet oxygen generating efficiencies of these chalcones are determined relative to rose bengal (RB). Superoxide dismutase (SOD) inhibitable cytochrome c reduction assay and electron magnetic resonance (EMR) spin trapping techniques are used to determine the superoxide anion radical (O-2(center dot-)) yield upon photoirradiation. Photoinduced DNA scission studies show that O-2(center dot-) is involved in the DNA strand break. In addition, antimicrobial activity of these chalcones is also investigated. Structure activity relationship accounts for the difference in the photogeneration of reactive oxygen species (ROS) by these sensitizers. Presence of electron releasing -OCH3 groups enhances the photogeneration of ROS. Cyclic voltammetry studies indicate a correlation between enzymatic O-2(center dot-) generation efficiency and redox potential of chalcones. Both O-2(center dot-) (Type I) and O-1(2) (Type II) paths are involved in the photosensitization of chalcones. The LUMO energies obtained by molecular modeling correlate with the one-electron reduction potentials. (C) 2010 Elsevier B.V. All rights reserved.
• Piperidine mediated synthesis of<i>n</i>-heterocyclic chalcones and their antibacterial activity
  作者：P. Venkatesan、S. Sumathi

  DOI：10.1002/jhet.268

  日期：——

  The chalcones 1-(2′-hydroxy-aryl)-3-(1-indol-3-yl)-prop-2-en-1-one (3) and 1-(2′-hydroxy-aryl)-3-(2-chloroquinolin-3-yl)-prop-2-en-1-one (6) were synthesised by piperidine mediated condensation of an ethanolic solution of an o-hydroxyacetophenone (1) with corresponding heteroaryl-3-carboxaldehyde. The structures have been established on the basis of elemental (C, H, N) analysis, UV, IR, 1H NMR spectral

  查耳酮1-（2'-羟基-芳基）-3-（1-吲哚-3-基）-丙-2-烯-1-一（3）和1-（2'-羟基-芳基）-3 -（2-氯喹啉-3-基）-丙-2-烯-1-酮（6）是通过哌啶介导的乙醇溶液缩合而合成的。邻羟基苯 乙酮（1）与相应的杂芳基-3-甲醛。该结构是根据元素（C，H，N）分析，UV，IR， 1 H NMR光谱数据建立的。化合物 和 筛选了针对多种细菌制剂的抗菌活性。J.杂环化​​学.2010。