(E)-2-(4-hydroxy-3-methoxybenzylidene)-6-((E)-3-(4-hydroxy-3-methoxyphenyl)acryloyl)cyclopentanone | 102569-94-8

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 二芳基庚烷
• 英文名称: (E)-2-(4-hydroxy-3-methoxybenzylidene)-6-((E)-3-(4-hydroxy-3-methoxyphenyl)acryloyl)cyclopentanone
• 英文别名: (2E)-2-[(4-hydroxy-3-methoxyphenyl)methylidene]-5-[(E)-3-(4-hydroxy-3-methoxyphenyl)prop-2-enoyl]cyclopentan-1-one
• CAS: 102569-94-8
• 化学式: C₂₃H₂₂O₆
• 分子量: 394.424
• InChiKey: UOKAOTPAXQCSIH-HFRHBYIXSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  29
• 可旋转键数：
  6
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.22
• 拓扑面积：
  93.1
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  1,10-菲罗啉 、 copper(II) choride dihydrate 、 水 、 (E)-2-(4-hydroxy-3-methoxybenzylidene)-6-((E)-3-(4-hydroxy-3-methoxyphenyl)acryloyl)cyclopentanone 在 三乙胺 作用下， 以 乙腈 为溶剂， 反应 5.0h， 以74%的产率得到
  参考文献：
  名称：

  Effects of Cu(II) and Zn(II) coordination on the trypanocidal activities of curcuminoid-based ligands

  摘要：

  Four heteroleptic metal complexes with the general formula [M(L1-2)(phen)Cl] 1a-b, 2a-b, (M = Cu(II) or Zn (II), L = curcuminoid ligand and phen = phenanthroline) have been prepared from the reaction of the ligands in the presence of Et3N with CuCl2 center dot 2H(2)O or ZnCl2. Characterization by IR, H-1 NMR and ERR spectroscopies, and X-ray diffraction analysis for lb confirmed the proposed structures for the complexes. The curcuminoid ligand coordinates in a deprotonated form as an O,O chelate, with phen and chloride completing the coordination sphere of the metal. The cytotoxic effects of ligands (HL1, HL2, phen) and complexes (1a-b, 2a-b) on the amastigote form of Trypanosoma cruzi have been screened. All substances showed significant toxicity. The Zn(II) complexes 1b (IC50 = 0.47 mu M, SI = 4.3) and 2b (IC50 = 0.40 mu M, SI = 3.8) were the most potent compounds being more toxic and selective against the parasite than the ligands and the copper complexes, thus implying that the coordinating metal is important for the trypanocidal activity of the curcumin-based compounds.

  DOI：

  10.1016/j.ica.2019.119237
• 作为产物：
  描述：

  2-乙酰基环戊酮 、 香草醛 在 硼酸三丁酯 、 氧化硼 、 仲丁胺 、 盐酸 、 水 作用下， 以 乙酸乙酯 为溶剂， 反应 3.83h， 以62%的产率得到(E)-2-(4-hydroxy-3-methoxybenzylidene)-6-((E)-3-(4-hydroxy-3-methoxyphenyl)acryloyl)cyclopentanone
  参考文献：
  名称：

  Effects of Cu(II) and Zn(II) coordination on the trypanocidal activities of curcuminoid-based ligands

  摘要：

  Four heteroleptic metal complexes with the general formula [M(L1-2)(phen)Cl] 1a-b, 2a-b, (M = Cu(II) or Zn (II), L = curcuminoid ligand and phen = phenanthroline) have been prepared from the reaction of the ligands in the presence of Et3N with CuCl2 center dot 2H(2)O or ZnCl2. Characterization by IR, H-1 NMR and ERR spectroscopies, and X-ray diffraction analysis for lb confirmed the proposed structures for the complexes. The curcuminoid ligand coordinates in a deprotonated form as an O,O chelate, with phen and chloride completing the coordination sphere of the metal. The cytotoxic effects of ligands (HL1, HL2, phen) and complexes (1a-b, 2a-b) on the amastigote form of Trypanosoma cruzi have been screened. All substances showed significant toxicity. The Zn(II) complexes 1b (IC50 = 0.47 mu M, SI = 4.3) and 2b (IC50 = 0.40 mu M, SI = 3.8) were the most potent compounds being more toxic and selective against the parasite than the ligands and the copper complexes, thus implying that the coordinating metal is important for the trypanocidal activity of the curcumin-based compounds.

  DOI：

  10.1016/j.ica.2019.119237

文献信息

• THERAPEUTIC COMPOSITIONS COMPRISING A COMBINATION OF A HARMINE AND ISOVANILLIN COMPONENT
  申请人：Ions Pharmaceutical S.À R.L.

  公开号：EP3275465A1

  公开（公告）日：2018-01-31

  Human therapeutic treatment compositions comprise the combination of at least one harmine component, and at least one isovanillin component, wherein the components of the composition are different. The compositions are effective for the treatment of human conditions, especially human cancers.

  人类治疗组合物由至少一种禾本科成分和至少一种异香兰素成分组合而成，其中组合物的成分各不相同。这些组合物可有效治疗人类疾病，尤其是人类癌症。
• Therapeutic compositions containing harmine and isovanillin components, and methods of use thereof
  申请人：Ankh Life Sciences Limited

  公开号：US10471049B2

  公开（公告）日：2019-11-12

  Human therapeutic treatment compositions comprise at least two of a curcumin component, a harmine component, and an isovanillin component, and preferably all three in combination. The agents are effective for the treatment of human conditions, especially human cancers.

  人类治疗组合物包含姜黄素成分、禾本科成分和异香兰素成分中的至少两种，最好是三种成分的组合。这些制剂可有效治疗人类疾病，尤其是人类癌症。
• Human therapeutic agents
  申请人：Ankh Life Sciences Limited

  公开号：US10744124B2

  公开（公告）日：2020-08-18

  Human therapeutic treatment compositions comprise at least two of a curcumin component, a harmine component, and an isovanillin component, and preferably all three in combination. The agents are effective for the treatment of human conditions, especially human cancers.

  人类治疗组合物包含姜黄素成分、禾本科成分和异香兰素成分中的至少两种，最好是三种成分的组合。这些制剂可有效治疗人类疾病，尤其是人类癌症。
• Samula, Kazimierz; Kardasz, Krystyna, Polish Journal of Chemistry, 1985, vol. 59, # 1, p. 73 - 77
  作者：Samula, Kazimierz、Kardasz, Krystyna

  DOI：——

  日期：——
• HUMAN THERAPEUTIC AGENTS
  申请人：Ankh Life Sciences Limited

  公开号：EP3188721B1

  公开（公告）日：2019-06-12