(2E)-1-(2'-hydroxy-3'-bromo-4',6'-dimethoxyphenyl)-3-(4-nitrophenyl)-2-propen-1-one | 1149368-10-4

• 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: (2E)-1-(2'-hydroxy-3'-bromo-4',6'-dimethoxyphenyl)-3-(4-nitrophenyl)-2-propen-1-one
• 英文别名: (E)-1-(3-bromo-2-hydroxy-4,6-dimethoxyphenyl)-3-(4-nitrophenyl)prop-2-en-1-one
• CAS: 1149368-10-4
• 化学式: C₁₇H₁₄BrNO₆
• 分子量: 408.205
• InChiKey: JDBNWYAOXFQJCM-VMPITWQZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.3
• 重原子数：
  25
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  102
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  2-hydroxy-3-bromo-4,6-dimethoxyacetophenone 、 对硝基苯甲醛 在 氢氧化钾 作用下， 以 甲醇 为溶剂， 反应 24.0h， 以42%的产率得到(2E)-1-(2'-hydroxy-3'-bromo-4',6'-dimethoxyphenyl)-3-(4-nitrophenyl)-2-propen-1-one
  参考文献：
  名称：

  Hydroxychalcones induce apoptosis in B16-F10 melanoma cells via GSH and ATP depletion

  摘要：

  Searching for leading compounds of new drugs for cancer therapy, we studied the toxicity of 13 hydroxychalcones never tested before toward melanoma cell line (B16-F10). The compounds were obtained by aldolic condensation between aldehydes and hydroxylated acetophenones, in alkaline conditions. Three of them showed cytotoxicity to the cell line. Two of them induced mitochondrial GSH and ATP depletion and promoted cell death through apoptosis in melanoma cells. One of the compounds induced cell death through necrosis but did not significantly decrease the intracellular mitochondrial GSH and ATP levels in melanoma cells. The results suggest that the predominant factor for the activity is the molecule shape, and secondarily the number of hydroxyl groups. (c) 2008 Published by Elsevier Masson SAS.

  DOI：

  10.1016/j.ejmech.2008.09.009

文献信息

• Hydroxychalcones induce apoptosis in B16-F10 melanoma cells via GSH and ATP depletion
  作者：Andréia Lilian Formento Navarini、Louise Domeneghini Chiaradia、Alessandra Mascarello、Márcio Fritzen、Ricardo José Nunes、Rosendo Augusto Yunes、Tânia Beatriz Creczynski-Pasa

  DOI：10.1016/j.ejmech.2008.09.009

  日期：2009.4

  Searching for leading compounds of new drugs for cancer therapy, we studied the toxicity of 13 hydroxychalcones never tested before toward melanoma cell line (B16-F10). The compounds were obtained by aldolic condensation between aldehydes and hydroxylated acetophenones, in alkaline conditions. Three of them showed cytotoxicity to the cell line. Two of them induced mitochondrial GSH and ATP depletion and promoted cell death through apoptosis in melanoma cells. One of the compounds induced cell death through necrosis but did not significantly decrease the intracellular mitochondrial GSH and ATP levels in melanoma cells. The results suggest that the predominant factor for the activity is the molecule shape, and secondarily the number of hydroxyl groups. (c) 2008 Published by Elsevier Masson SAS.