(2E)-1-(1,3-benzodioxol-5-yl)-3-(3-nitrophenyl)-2-propen-1-one | 1252015-02-3

• 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: (2E)-1-(1,3-benzodioxol-5-yl)-3-(3-nitrophenyl)-2-propen-1-one
• 英文别名: (E)-1-(1,3-benzodioxol-5-yl)-3-(3-nitrophenyl)prop-2-en-1-one
• CAS: 1252015-02-3
• 化学式: C₁₆H₁₁NO₅
• 分子量: 297.267
• InChiKey: DXIFNBLJXZHOGP-GQCTYLIASA-N

物化性质

• 熔点：
  144-146 °C(Solv: methanol (67-56-1))
• 沸点：
  498.6±45.0 °C(Predicted)
• 密度：
  1.396±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  22
• 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：
  81.4
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  3,4-亚甲二氧苯乙酮 、 间硝基苯甲醛 在 potassium hydroxide 作用下， 以 甲醇 为溶剂， 反应 24.0h， 生成 (2E)-1-(1,3-benzodioxol-5-yl)-3-(3-nitrophenyl)-2-propen-1-one
  参考文献：
  名称：

  Synthetic compounds from an in house library as inhibitors of falcipain-2 from Plasmodium falciparum

  摘要：

  Falcipain-2 (FP-2) is a key cysteine protease from the malaria parasite Plasmodium falciparum. Many previous studies have identified FP-2 inhibitors; however, none has yet met the criteria for an antimalarial drug candidate. In this work, we assayed an in-house library of non-peptidic organic compounds, including (E)-chalcones, (E)-N'-benzylidene-benzohydrazides and alkylesters of gallic acid, and assessed the activity toward FP-2 and their mechanisms of inhibition. The (E)-chalcones 48, 54 and 66 showed the lowest IC50 values (8.5 +/- 0.8 mu M, 9.5 +/- 0.2 mu M and 4.9 +/- 1.3 mu M, respectively). The best inhibitor (compound 66) demonstrated non-competitive inhibition, and using mass spectrometry and fluorescence spectroscopy assays, we suggest a potential allosteric site for the interaction of this compound, located between the catalytic site and the hemoglobin binding arm in FP-2. We combined structural biology tools and mass spectrometry to characterize the inhibition mechanisms of novel compounds targeting FP-2.

  DOI：

  10.3109/14756366.2014.920839