7-difluoromethyl-5,4'-dipropoxygenistein | 848565-60-6

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 异黄酮类化合物
• 英文名称: 7-difluoromethyl-5,4'-dipropoxygenistein
• 英文别名: 4',5-DI-N-Propoxy-7-gem-difluoromethylenated genistein；7-(difluoromethoxy)-5-propoxy-3-(4-propoxyphenyl)chromen-4-one
• CAS: 848565-60-6
• 化学式: C₂₂H₂₂F₂O₅
• 分子量: 404.41
• InChiKey: MPPSPYOQYYUHON-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.8
• 重原子数：
  29
• 可旋转键数：
  9
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.32
• 拓扑面积：
  54
• 氢给体数：
  0
• 氢受体数：
  7

反应信息

• 作为产物：
  描述：

  7-O-difluoromethylgenistein 、 alkaline earth salt of/the/ methylsulfuric acid 在 potassium carbonate 作用下， 以 丙酮 为溶剂， 以86.3%的产率得到7-difluoromethyl-5,4'-dipropoxygenistein
  参考文献：
  名称：

  Synthesis and cytotoxic activity of genistein derivatives

  摘要：

  A series of genistein derivatives was prepared and tested in vitro against leukocythemia (HL-60), colorectal adenocarcinoma (HT-29), and human gastric adenocarcinoma (SGC-7901) cell lines. Among these derivatives, 4',5-di-n-octoxy-7-gem-difluoromethylenegenistein, 9f, had the strongest activity against HL-60, HT-29, and SGC-7901 cells.

  DOI：

  10.1007/s00044-009-9271-z

文献信息

• Synthesis of genistein derivatives and determination of their protective effects against vascular endothelial cell damages caused by hydrogen peroxide
  作者：Xiao-Hua Fu、Li Wang、Hong Zhao、Hong-Lin Xiang、Jian-Guo Cao

  DOI：10.1016/j.bmcl.2007.11.097

  日期：2008.1

  A series of genistein derivatives, prepared by alkylation and difluoromethylation, were tested for their inhibitory effects on the hydrogen peroxide induced impairment in human umbilical vein endothelial (HUVE-12) cells in vitro. The HUVE-12 cells were pretreated with either the vehicle solvent (DMSO), genistein, or different amounts of the genistein derivatives for 30 min before exposed to 1 mM hydrogen peroxide for 24 h. Cell apoptosis was determined by flow cytometry with propidium iodide (PI) staining. Cellular injury was estimated by measuring the lactate dehydrogenase (LDH) release. Data suggested that the genistein derivatives possessed a protective effect on HUVE-12 cells from hydrogen peroxide induced apoptosis and reduced LDH release. Among these derivatives, 7-difluoromethyl-5,4'-dimethoxygenistein exhibited the strongest activity against hydrogen peroxide induced apoptosis of HUVE-12 cells. (c) 2007 Elsevier Ltd. All rights reserved.
• Synthesis and cytotoxic activity of genistein derivatives
  作者：Xing Zheng、Xu Yao、Yunmei Liu、Zitong Zheng、Jianguo Cao、Duanfang Liao

  DOI：10.1007/s00044-009-9271-z

  日期：2010.12

  A series of genistein derivatives was prepared and tested in vitro against leukocythemia (HL-60), colorectal adenocarcinoma (HT-29), and human gastric adenocarcinoma (SGC-7901) cell lines. Among these derivatives, 4',5-di-n-octoxy-7-gem-difluoromethylenegenistein, 9f, had the strongest activity against HL-60, HT-29, and SGC-7901 cells.