2,6-dibromo-3,3',4,4',5-pentahydroxydiphenylmethanone | 1203560-60-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 2,6-dibromo-3,3',4,4',5-pentahydroxydiphenylmethanone
• 英文别名: (2,6-Dibromo-3,4,5-trihydroxyphenyl)-(3,4-dihydroxyphenyl)methanone
• CAS: 1203560-60-4
• 化学式: C₁₃H₈Br₂O₆
• 分子量: 420.011
• InChiKey: GXXOTUGFHIBIBW-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  21
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  118
• 氢给体数：
  5
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  2,6-dibromo-3,3',4,4',5-pentamethoxydiphenylmethanone 在 三溴化硼 作用下， 以 二氯甲烷 为溶剂， 反应 4.0h， 生成 2,6-dibromo-3,3',4,4',5-pentahydroxydiphenylmethanone
  参考文献：
  名称：

  Synthesis and biological activity of halophenols as potent antioxidant and cytoprotective agents

  摘要：

  A series of new bromophenols and chlorophenols were prepared by a practical route. The in vitro antioxidative activity of the halophenols was evaluated by the 1,1-diphenyl-2-picrylhydrazyl (DPPH) radical-scavenging assay, and their cytoprotective activity was also tested on hydrogen peroxide (H2O2)-induced injury in human umbilical vein endothelial cells (HUVEC). All halophenols tested displayed moderate to good DPPH radical-scavenging activity, and two bromophenols, 2,3'-dibromo-4,5,6'-trihydroxydiphenyl-methanone (16c) and 2,3-dibromo-4,5-dihydroxydiphenylmethanone (17c) exhibited high protective activity against H2O2-induced injury in HUVEC with EC50 values of 0.4 and 0.8 mu M, respectively. The preliminary structure-activity relationships of these compounds were also investigated in order to determine the essential structures required for their bioactivities. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2010.05.068

文献信息

• Synthesis and biological activity of halophenols as potent antioxidant and cytoprotective agents
  作者：Wanyi Zhao、Xiue Feng、Shurong Ban、Wenhan Lin、Qingshan Li

  DOI：10.1016/j.bmcl.2010.05.068

  日期：2010.7

  A series of new bromophenols and chlorophenols were prepared by a practical route. The in vitro antioxidative activity of the halophenols was evaluated by the 1,1-diphenyl-2-picrylhydrazyl (DPPH) radical-scavenging assay, and their cytoprotective activity was also tested on hydrogen peroxide (H2O2)-induced injury in human umbilical vein endothelial cells (HUVEC). All halophenols tested displayed moderate to good DPPH radical-scavenging activity, and two bromophenols, 2,3'-dibromo-4,5,6'-trihydroxydiphenyl-methanone (16c) and 2,3-dibromo-4,5-dihydroxydiphenylmethanone (17c) exhibited high protective activity against H2O2-induced injury in HUVEC with EC50 values of 0.4 and 0.8 mu M, respectively. The preliminary structure-activity relationships of these compounds were also investigated in order to determine the essential structures required for their bioactivities. (C) 2010 Elsevier Ltd. All rights reserved.