trans-3-(3-ethoxy-4-methoxyphenyl)-1-(4-hydroxyphenyl)propenone | 1002797-45-6

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 直链 1,3-二芳基丙烷
• 英文名称: trans-3-(3-ethoxy-4-methoxyphenyl)-1-(4-hydroxyphenyl)propenone
• 英文别名: (E)-3-(4-ethoxy-3-methoxyphenyl)-1-(4-hydroxyphenyl)prop-2-en-1-one
• CAS: 1002797-45-6
• 化学式: C₁₈H₁₈O₄
• 分子量: 298.339
• InChiKey: AZMNFNUSAHWFNK-ONNFQVAWSA-N

物化性质

• 熔点：
  212-214 °C(Solvent: Methanol)
• 沸点：
  495.8±45.0 °C(Predicted)
• 密度：
  1.180±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  22
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  55.8
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  3-吡啶甲酰肼 、 trans-3-(3-ethoxy-4-methoxyphenyl)-1-(4-hydroxyphenyl)propenone 以 甲醇 为溶剂， 反应 72.0h， 以43%的产率得到[5-(4-ethoxy-3-methoxyphenyl)-3-(4-hydroxyphenyl)-4,5-dihydropyrazol-1-yl]pyridin-3-yl-methanone
  参考文献：
  名称：

  Pharmacophore based discovery of potential antimalarial agent targeting haem detoxification pathway

  摘要：

  Pharmacophore hypotheses were generated from molecules having putative antimalarial activities targeting haem detoxification pathway of malarial parasite. A training set consisting of 33 compounds, whose activities were evaluated for haem polymerization inhibition and against chloroquine resistant (K1) strain of Plasmodium falciparum, was optimized to generate hypotheses. The hypothesis showing optimum correlation between actual and estimated activities was validated by Fischer's randomization test at 95% confidence level and used as a model to screen our in-house compound database. Nicotinic acid [trans-3-(4-ethoxy-3-methoxy-phenyl)-1-(4-hydroxy-phenyl)-allylidene]-hydrazide (ALH5) was obtained as a hit. The compound was synthesized and evaluated against chloroquine sensitive (MRC-02) and resistant (RKL9) strains of malarial parasite P. falciparum. The compound showed antimalarial activity in nanomolar range and was found comparable with chloroquine. (C) 2008 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2008.02.005
• 作为产物：
  描述：

  4-乙氧基-3-甲氧基苯甲醛 、 对羟基苯乙酮 在 sodium methylate 作用下， 以 甲醇 为溶剂， 反应 24.0h， 以65%的产率得到trans-3-(3-ethoxy-4-methoxyphenyl)-1-(4-hydroxyphenyl)propenone
  参考文献：
  名称：

  Pharmacophore based discovery of potential antimalarial agent targeting haem detoxification pathway

  摘要：

  Pharmacophore hypotheses were generated from molecules having putative antimalarial activities targeting haem detoxification pathway of malarial parasite. A training set consisting of 33 compounds, whose activities were evaluated for haem polymerization inhibition and against chloroquine resistant (K1) strain of Plasmodium falciparum, was optimized to generate hypotheses. The hypothesis showing optimum correlation between actual and estimated activities was validated by Fischer's randomization test at 95% confidence level and used as a model to screen our in-house compound database. Nicotinic acid [trans-3-(4-ethoxy-3-methoxy-phenyl)-1-(4-hydroxy-phenyl)-allylidene]-hydrazide (ALH5) was obtained as a hit. The compound was synthesized and evaluated against chloroquine sensitive (MRC-02) and resistant (RKL9) strains of malarial parasite P. falciparum. The compound showed antimalarial activity in nanomolar range and was found comparable with chloroquine. (C) 2008 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2008.02.005

文献信息

• Pharmacophore based discovery of potential antimalarial agent targeting haem detoxification pathway
  作者：Badri Narayan Acharya、Deepika Saraswat、Mahabir Parshad Kaushik

  DOI：10.1016/j.ejmech.2008.02.005

  日期：2008.12

  Pharmacophore hypotheses were generated from molecules having putative antimalarial activities targeting haem detoxification pathway of malarial parasite. A training set consisting of 33 compounds, whose activities were evaluated for haem polymerization inhibition and against chloroquine resistant (K1) strain of Plasmodium falciparum, was optimized to generate hypotheses. The hypothesis showing optimum correlation between actual and estimated activities was validated by Fischer's randomization test at 95% confidence level and used as a model to screen our in-house compound database. Nicotinic acid [trans-3-(4-ethoxy-3-methoxy-phenyl)-1-(4-hydroxy-phenyl)-allylidene]-hydrazide (ALH5) was obtained as a hit. The compound was synthesized and evaluated against chloroquine sensitive (MRC-02) and resistant (RKL9) strains of malarial parasite P. falciparum. The compound showed antimalarial activity in nanomolar range and was found comparable with chloroquine. (C) 2008 Elsevier Masson SAS. All rights reserved.