1-(2-Hydroxy-3-prop-2-enylphenyl)-3-(3-methylphenyl)prop-2-en-1-one | 600151-58-4

• 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: 1-(2-Hydroxy-3-prop-2-enylphenyl)-3-(3-methylphenyl)prop-2-en-1-one
• CAS: 600151-58-4
• 化学式: C₁₉H₁₈O₂
• 分子量: 278.351
• InChiKey: KCDIGYFJAVXWEG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.3
• 重原子数：
  21
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.11
• 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：

  1-(2-Hydroxy-3-prop-2-enylphenyl)-3-(3-methylphenyl)prop-2-en-1-one 在 sodium hydroxide 、 双氧水 作用下， 以 乙醇 为溶剂， 以19%的产率得到3-Hydroxy-2-(3-methylphenyl)-8-prop-2-enylchromen-4-one
  参考文献：
  名称：

  Synthesis and Biological Evaluation of 3-Alkoxy Analogues of Flavone-8-acetic Acid

  摘要：

  New analogues of flavone-8-acetic acid were synthesized, bearing an alkoxy group in position 3 and different substituents on the benzene ring in position 2 of the flavone nucleus. The compounds were tested for direct cytotoxicity against four human tumor cell lines and for indirect antitumor effects by measuring their ability to enhance lytic properties of murine macrophages and human monocytes. Though direct toxicity was very low, the compounds were able to induce significant indirect toxicity. Notably, most of them (4c, 4d, 4e, 4f, 4h, 4i, 4m, 4n, and 4o) showed important activity on human monocytes and could be regarded as the first flavone derivatives endowed with such activity. Particularly interesting seem to be compounds 4m and 4n, which showed IC50 values up to 7 times higher than DMXAA, which has now completed phase I clinical trials.

  DOI：

  10.1021/jm030771o
• 作为产物：
  描述：

  1-(3-烯丙基-2-羟基苯基)乙酮 、 3-甲基苯甲醛 在 氢氧化钾 作用下， 以 乙醇 为溶剂， 以45%的产率得到1-(2-Hydroxy-3-prop-2-enylphenyl)-3-(3-methylphenyl)prop-2-en-1-one
  参考文献：
  名称：

  Synthesis and Biological Evaluation of 3-Alkoxy Analogues of Flavone-8-acetic Acid

  摘要：

  New analogues of flavone-8-acetic acid were synthesized, bearing an alkoxy group in position 3 and different substituents on the benzene ring in position 2 of the flavone nucleus. The compounds were tested for direct cytotoxicity against four human tumor cell lines and for indirect antitumor effects by measuring their ability to enhance lytic properties of murine macrophages and human monocytes. Though direct toxicity was very low, the compounds were able to induce significant indirect toxicity. Notably, most of them (4c, 4d, 4e, 4f, 4h, 4i, 4m, 4n, and 4o) showed important activity on human monocytes and could be regarded as the first flavone derivatives endowed with such activity. Particularly interesting seem to be compounds 4m and 4n, which showed IC50 values up to 7 times higher than DMXAA, which has now completed phase I clinical trials.

  DOI：

  10.1021/jm030771o

文献信息

• Synthesis and Biological Evaluation of 3-Alkoxy Analogues of Flavone-8-acetic Acid
  作者：Silvia Gobbi、Angela Rampa、Alessandra Bisi、Federica Belluti、Lorna Piazzi、Piero Valenti、Anna Caputo、Antonella Zampiron、Maria Carrara

  DOI：10.1021/jm030771o

  日期：2003.8.1

  New analogues of flavone-8-acetic acid were synthesized, bearing an alkoxy group in position 3 and different substituents on the benzene ring in position 2 of the flavone nucleus. The compounds were tested for direct cytotoxicity against four human tumor cell lines and for indirect antitumor effects by measuring their ability to enhance lytic properties of murine macrophages and human monocytes. Though direct toxicity was very low, the compounds were able to induce significant indirect toxicity. Notably, most of them (4c, 4d, 4e, 4f, 4h, 4i, 4m, 4n, and 4o) showed important activity on human monocytes and could be regarded as the first flavone derivatives endowed with such activity. Particularly interesting seem to be compounds 4m and 4n, which showed IC50 values up to 7 times higher than DMXAA, which has now completed phase I clinical trials.