4-Hydroxy-3-<3-furyl-(2)-acryloyl>-cumarin | 57340-06-4

• 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-furyl-(2)-acryloyl>-cumarin
• 英文别名: 1-(4-hydroxy-2-oxo-2H-chromen-3-yl)-3-(furan-2-yl)-2-propen-1-one；3-(3-furan-2-yl-acryloyl)-4-hydroxy-chromen-2-one
• CAS: 57340-06-4
• 化学式: C₁₆H₁₀O₅
• 分子量: 282.252
• InChiKey: IXEQLIKVEUBGKR-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.99
• 重原子数：
  21.0
• 可旋转键数：
  3.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  80.65
• 氢给体数：
  1.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  4-Hydroxy-3-<3-furyl-(2)-acryloyl>-cumarin 在 一水合肼 作用下， 以 乙醇 为溶剂， 生成 4-Hydroxy-3-<3-furyl-(2)-pyrazolinyl-(5)>-cumarin
  参考文献：
  名称：

  Mustafa,A. et al., Justus Liebigs Annalen der Chemie, 1965, vol. 684, p. 194 - 200

  摘要：

  DOI：
• 作为产物：
  描述：

  4-羟基香豆素 在 哌啶 、 三氯氧磷 作用下， 以 氯仿 为溶剂， 生成 4-Hydroxy-3-<3-furyl-(2)-acryloyl>-cumarin
  参考文献：
  名称：

  Design, synthesis and biological evaluation of some novel 3-cinnamoyl-4-hydroxy-2H-chromen-2-ones as antimalarial agents

  摘要：

  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.

  DOI：

  10.1007/s00044-011-9694-1

文献信息

• Synthesis, anticoagulant and PIVKA-II induced by new 4-hydroxycoumarin derivatives
  作者：Omaima M. Abdelhafez、Kamelia M. Amin、Rasha Z. Batran、Timothy J. Maher、Somaia A. Nada、Shalini Sethumadhavan

  DOI：10.1016/j.bmc.2010.04.009

  日期：2010.5

  The action of the coumarin-type drugs and related compounds is reviewed to their VKOR antagonistic effects. In our study, twenty 3-pyridinyl, pyrimidinyl and pyrazolyl-4-hydroxycoumarin derivatives were synthesized. A comparative in vivo (CT, PT determination) and in vitro ( measurement of PIVKA-II levels) anticoagulant study with respect to warfarin showed that the synthesized compounds have different anticoagulant activities, the most prospective compounds were the 3-pyrazolyl-4-hydroxycoumarin derivatives. (C) 2010 Elsevier Ltd. All rights reserved.
• Mustafa,A. et al., Justus Liebigs Annalen der Chemie, 1965, vol. 684, p. 194 - 200
  作者：Mustafa,A. et al.

  DOI：——

  日期：——
• 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.

表征谱图