(E)-3-(3-羟基苯基)-1-(3-甲基苯基)丙-2-烯-1-酮 | 153976-41-1

• 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
• 中文名称: (E)-3-(3-羟基苯基)-1-(3-甲基苯基)丙-2-烯-1-酮
• 英文名称: 3-hydroxy-3'-methylchalcone
• 英文别名: 3'-Methyl-3-hydroxychalcone；(E)-3-(3-hydroxyphenyl)-1-(3-methylphenyl)prop-2-en-1-one
• CAS: 153976-41-1；153976-43-3
• 化学式: C₁₆H₁₄O₂
• 分子量: 238.286
• InChiKey: GPJXEEMHEDUKIP-CMDGGOBGSA-N

物化性质

• 沸点：
  440.0±45.0 °C(Predicted)
• 密度：
  1.165±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  18
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.06
• 拓扑面积：
  37.3
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (E)-3-(3-羟基苯基)-1-(3-甲基苯基)丙-2-烯-1-酮 以 甲醇 为溶剂， 反应 168.0h， 以85%的产率得到cis-3-hydroxy-3'-methylchalcone
  参考文献：
  名称：

  Antitumorigenic Activities of Chalcones (II). Photo-isomerization of Chalcones and the Correlation with Their Biological Activities.

  摘要：

  Some chalcones are known to be phototransformed in a solution from trans into cis isomers. 3-Hydroxy-3'-methylchalcone (3'Me-3-C) has been found to be isomerized from trans into cis by irradiation of daylight in the methanolic solution. The presence of a hydroxyl in the 2'- or 4-position in the trans-chalcone structure prevents phototransformation into cis isomers. The feasibility of phototransformation of chalcones was discussed using UV-spectral analysis. The phototransformed cis-3'Me-3-C showed more potent antitumorigenic activity than the original trans form.The generally recognized parallelism between antitumorigenic and antiinflammatory, activities was not observed in trans and cis 3'-Me- and 4'-Me-3C, which are antitumorigenic but inactive in 12-O-tetradecanoylphorbol 13-acetate (TPA)- and arachidonic acid (AA)-induced mouse ear edema. However, inhibitory activity against ornithine-decarboxylase (ODC) was commonly observed in both naturally occurring and synthetic antitumorigenic chalcones.

  DOI：

  10.1248/bpb.20.1266
• 作为产物：
  描述：

  间羟基苯甲醛 、 3'-甲基苯乙酮 在 氢氧化钾 作用下， 以 乙醇 为溶剂， 反应 24.0h， 以23%的产率得到(E)-3-(3-羟基苯基)-1-(3-甲基苯基)丙-2-烯-1-酮
  参考文献：
  名称：

  Antitumorigenic Activities of Chalcones. I. Inhibitory Effects of Chalcone Derivatives on 32Pi-Incorporation into Phospholipids of HeLa Cells Promoted by 12-O-Tetradecanoyl-phorbol 13-Acetate(TPA).

  摘要：

  合成了四十余种查耳酮衍生物，以研究其结构与抗肿瘤发生活性之间的关系。作为初步筛选测试，检测了查耳酮对12-O-十四烷酰佛波醇-13-乙酸酯（TPA）增强的HeLa细胞磷脂中32Pi掺入的抑制活性。在3'-、4'-或2'-位具有甲基的3-羟基查耳酮衍生物和异甘草素同系物在磷酸化试验中显示出强大的抑制活性，这表明它们具有抗肿瘤发生作用。

  DOI：

  10.1248/bpb.18.1710

文献信息

• 1-Adamantyl chalcones for the treatment of proliferative disorders
  申请人：Anderson L. Gloria

  公开号：US20050065152A1

  公开（公告）日：2005-03-24

  The present invention relates to the compounds of the general formula (I), a composition for and a method of treating breast cancer or other proliferative disorders in a subject using a compound of general formula [I], wherein the substituents are as defined in the specification.

  本发明涉及通式(I)化合物、使用通式[I]化合物治疗乳腺癌或其他增殖性疾病的组合物和方法、 其中取代基如说明书中所定义。
• JPH06122623A
  申请人：——

  公开号：JPH06122623A

  公开（公告）日：1994-05-06
• JPH09309860A
  申请人：——

  公开号：JPH09309860A

  公开（公告）日：1997-12-02
• Methods and compositions for the treatment of neurodegenerative disorders
  申请人：Jin Xiaowei

  公开号：US20080044390A1

  公开（公告）日：2008-02-21

  The present invention features compositions, kits, and methods for treating, preventing, and ameliorating neurodegenerative disorders, e.g., Huntington's disease.
• 1-ADAMANTYL CHALCONES FOR THE TREATMENT OF PROLIFERATIVE DISORDERS
  申请人：Anderson Gloria L.

  公开号：US20090281196A1

  公开（公告）日：2009-11-12

  The present invention relates to the compounds of the general formula (I), a composition for and a method of treating breast cancer or other proliferative disorders in a subject using a compound of general formula [I], wherein the substituents are as defined in the specification.