2-phenyl-7-(prop-2-yn-1-yloxy)-4H-chromen-4-one | 67091-11-6

• 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: 2-phenyl-7-(prop-2-yn-1-yloxy)-4H-chromen-4-one
• 英文别名: 7-(prop-2-yn-1-yloxy)flavone；7-Propargyloxyflavone；2-phenyl-7-prop-2-ynyloxy-chromen-4-one；7-Propargyloxy-flavon；2-Phenyl-7-prop-2-ynoxychromen-4-one
• CAS: 67091-11-6
• 化学式: C₁₈H₁₂O₃
• 分子量: 276.291
• InChiKey: PSYLUGSEPAFNFV-UHFFFAOYSA-N

物化性质

• 熔点：
  200-201 °C(Solv: methanol (67-56-1))
• 沸点：
  461.9±45.0 °C(Predicted)
• 密度：
  1?+-.0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.1
• 重原子数：
  21
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.06
• 拓扑面积：
  35.5
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2-phenyl-7-(prop-2-yn-1-yloxy)-4H-chromen-4-one 在 N,N-二乙基苯胺 作用下， 以65%的产率得到2-phenyl-8H-pyrano[2,3-h]chromen-4-one
  参考文献：
  名称：

  Pyranoflavones: A Group of Small-Molecule Probes for Exploring the Active Site Cavities of Cytochrome P450 Enzymes 1A1, 1A2, and 1B1

  摘要：

  Selective inhibition of P450 enzymes is the key to block the conversion of environmental procarcinogens to their carcinogenic metabolites in both animals and humans. To discover highly potent and selective inhibitors of P450s 1A1, 1A2, and 1B1, as well as to investigate active site cavities of these enzymes, 14 novel flavone derivatives were prepared as chemical probes. Fluorimetric enzyme inhibition assays were used to determine the inhibitory activities of these probes toward P450s 1A1, 1A2, 1B1, 2A6, and 2B1. A highly selective P450 1B1 inhibitor 5-hydroxy-4'-propargyloxyflavone (5H4'FPE) was discovered. Some tested compounds also showed selectivity between P450s 1A1 and 1A2. a-Naphthoflavone-like and 5-hydroxyflavone derivatives preferentially inhibited P450 1A2, while beta-naphthoflavone-like flavone derivatives showed selective inhibition of P450 1A1. On the basis of structural analysis, the active site cavity models of P450 enzymes 1A1 and 1A2 were generated, demonstrating a planar long strip cavity and a planar triangular cavity, respectively.

  DOI：

  10.1021/jm4003654
• 作为产物：
  描述：

  1-(2,4-二羟基苯基)-3-苯基丙烷-1,3-二酮 在 sodium acetate 、 potassium carbonate 、 溶剂黄146 作用下， 以 丙酮 为溶剂， 反应 27.5h， 生成 2-phenyl-7-(prop-2-yn-1-yloxy)-4H-chromen-4-one
  参考文献：
  名称：

  五元杂环（或酰胺）-黄酮类化合物-苦参碱三元轭联物和用途

  摘要：

  本发明公开了五元杂环(或酰胺)-黄酮类化合物-苦参碱三元轭联物和用途。所述的五元杂环(或酰胺)-黄酮类化合物-苦参碱三元轭联物和用途具有如下结构：本发明的五元杂环(或酰胺)-黄酮类化合物-苦参碱三元轭联物具有高效的抗菌活性，在抗菌药物开发方面具有潜在的应用价值。本发明所涉及的五元杂环(或酰胺)-黄酮类化合物-苦参碱三元轭联物在抗菌方面有显著的效果，可用于预防和治疗MRSA，P.aeru，E.coli，Ab等临床常见致病菌。

  公开号：

  CN105440033A

文献信息

• Microwave-Assisted Synthesis of Novel Bis-Flavone Dimers as New Anticancer Agents
  作者：Andrew McGown、Abby Ragazzon-Smith、John A. Hadfield、Herman Potgetier、Patricia A. Ragazzon

  DOI：10.2174/1570178615666180621094529

  日期：2018.12.4