(1E,4Z,6E)-1,7-bis(4-hydroxy-3-methoxyphenyl)-5-(1-phenylethylamino)hepta-1,4,6-trien-3-one | 1010805-63-6

• 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: (1E,4Z,6E)-1,7-bis(4-hydroxy-3-methoxyphenyl)-5-(1-phenylethylamino)hepta-1,4,6-trien-3-one
• CAS: 1010805-63-6
• 化学式: C₂₉H₂₉NO₅
• 分子量: 471.553
• InChiKey: MAPROPNFUHYPEJ-NQCFXFOASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.2
• 重原子数：
  35
• 可旋转键数：
  10
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.14
• 拓扑面积：
  88
• 氢给体数：
  3
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  curcumin 、 α-苯乙胺 在 溶剂黄146 作用下， 以 甲醇 、 苯 为溶剂， 生成 (1E,4Z,6E)-1,7-bis(4-hydroxy-3-methoxyphenyl)-5-(1-phenylethylamino)hepta-1,4,6-trien-3-one
  参考文献：
  名称：

  Antitumor effects of curcumin and structurally β-diketone modified analogs on multidrug resistant cancer cells

  摘要：

  Using concepts of bioisostery a series of curcumin analogs were synthesized: the diketonic system of the compound was elaborated into enamitiones, oximes, and the isoxazole heterocycle. The cell growth inhibitory and apoptosis inducing effects of the new analogs were evaluated by in vitro assays in the hepatocellular carcinoma HA22T/VGH cells, as well as in the MCF-7 breast cancer cell line and in its multidrug resistant (MDR) variant MCF-7R. Increased antitumor activity on all cell lines was found with the isoxazole analog and especially with the benzyl oxime derivative; in the HA22T/VGH cell model, the latter compound inhibited constitutive NF-kappa B activation. (c) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2007.11.021

文献信息

• Antitumor effects of curcumin and structurally β-diketone modified analogs on multidrug resistant cancer cells
  作者：Daniele Simoni、Michele Rizzi、Riccardo Rondanin、Riccardo Baruchello、Paolo Marchetti、Francesco Paolo Invidiata、Manuela Labbozzetta、Paola Poma、Valeria Carina、Monica Notarbartolo、Alessandra Alaimo、Natale D’Alessandro

  DOI：10.1016/j.bmcl.2007.11.021

  日期：2008.1

  Using concepts of bioisostery a series of curcumin analogs were synthesized: the diketonic system of the compound was elaborated into enamitiones, oximes, and the isoxazole heterocycle. The cell growth inhibitory and apoptosis inducing effects of the new analogs were evaluated by in vitro assays in the hepatocellular carcinoma HA22T/VGH cells, as well as in the MCF-7 breast cancer cell line and in its multidrug resistant (MDR) variant MCF-7R. Increased antitumor activity on all cell lines was found with the isoxazole analog and especially with the benzyl oxime derivative; in the HA22T/VGH cell model, the latter compound inhibited constitutive NF-kappa B activation. (c) 2007 Elsevier Ltd. All rights reserved.