4-hydroxy-3-(3-(4-hydroxy-3-methoxyphenyl)-1-oxo-2-propen-1-yl)-2H-1-benzopyran-2-one | 57339-90-9

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 香豆素及其衍生物
• 英文名称: 4-hydroxy-3-(3-(4-hydroxy-3-methoxyphenyl)-1-oxo-2-propen-1-yl)-2H-1-benzopyran-2-one
• 英文别名: 4-hydroxy-3-[3-(4-hydroxy-3-methoxyphenyl)prop-2-enoyl]chromen-2-one
• CAS: 57339-90-9
• 化学式: C₁₉H₁₄O₆
• 分子量: 338.317
• InChiKey: LQZHHEFLZZQRNA-UHFFFAOYSA-N

物化性质

• 沸点：
  575.1±50.0 °C(Predicted)
• 密度：
  1.454±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.11
• 重原子数：
  25.0
• 可旋转键数：
  4.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.05
• 拓扑面积：
  96.97
• 氢给体数：
  2.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  4-hydroxy-3-(3-(4-hydroxy-3-methoxyphenyl)-1-oxo-2-propen-1-yl)-2H-1-benzopyran-2-one 在 hydrazine hydrate 作用下， 以 乙醇 为溶剂， 以72%的产率得到3-(4,5-dihydro-5-(4-hydroxy-3-methoxyphenyl)-1H-pyrazol-3-yl)-4-hydroxy-2H-chromen-2-one
  参考文献：
  名称：

  Angiokinase inhibition of VEGFR-2, PDGFR and FGFR and cell growth inhibition in lung cancer: Design, synthesis, biological evaluation and molecular docking of novel azaheterocyclic coumarin derivatives

  摘要：

  DOI：

  10.1016/j.bmcl.2021.128258
• 作为产物：
  描述：

  4-羟基香豆素 在 potassium hydroxide 、 三氯氧磷 作用下， 以 乙醇 为溶剂， 反应 24.5h， 生成 4-hydroxy-3-(3-(4-hydroxy-3-methoxyphenyl)-1-oxo-2-propen-1-yl)-2H-1-benzopyran-2-one
  参考文献：
  名称：

  Angiokinase inhibition of VEGFR-2, PDGFR and FGFR and cell growth inhibition in lung cancer: Design, synthesis, biological evaluation and molecular docking of novel azaheterocyclic coumarin derivatives

  摘要：

  DOI：

  10.1016/j.bmcl.2021.128258

文献信息

• Design, synthesis and biological evaluation of some novel 3-cinnamoyl-4-hydroxy-2H-chromen-2-ones as antimalarial agents
  作者：Kuldeep Patel、Chandrabose Karthikeyan、N. S. Hari Narayana Moorthy、Girdhar Singh Deora、Viswas Raja Solomon、Hoyun Lee、Piyush Trivedi

  DOI：10.1007/s00044-011-9694-1

  日期：2012.8

  A novel series of 3-cinnamoyl-4-hydroxy-2H-chromen-2-ones were designed, synthesized and screened for antiplasmodial activity. Eleven compounds of the series exhibited micromolar potency against chloroquine sensitive and chloroquine resistant strains. The most potent compound 4-hydroxy-3-(3-(4-nitrophenyl)acryloyl)-2H-chromen-2-one showed inhibitory potency (IC50) of 3.1 and 4 mu g/ml against chloroquine sensitive and chloroquine resistant strains, respectively. A structure activity relationship study was performed by correlating the effect of substituents with the antimalarial activity of the title compounds. The novel 3-cinnamoyl-4-hydroxy-2H-chromen-2-ones reported here should be good lead for further development of antimalarial agents that can overcome resistance.

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