11-O-p-hydroxybenzoyl-tri-O-methylnorbergenin

• 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: 11-O-p-hydroxybenzoyl-tri-O-methylnorbergenin
• 英文别名: [(2R,3S,4S,4aR,10bS)-3,4-dihydroxy-8,9,10-trimethoxy-6-oxo-3,4,4a,10b-tetrahydro-2H-pyrano[3,2-c]isochromen-2-yl]methyl 4-hydroxybenzoate
• 化学式: C₂₃H₂₄O₁₁
• 分子量: 476.437
• InChiKey: SOHPUUSQOUJRII-VKUPYFBZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.98
• 重原子数：
  34.0
• 可旋转键数：
  6.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.39
• 拓扑面积：
  150.21
• 氢给体数：
  3.0
• 氢受体数：
  11.0

反应信息

• 作为产物：
  描述：

  岩白菜素 在 偶氮二甲酸二异丙酯 、 potassium carbonate 、 三苯基膦 作用下， 以 四氢呋喃 、 N,N-二甲基甲酰胺 为溶剂， 反应 3.0h， 生成 11-O-p-hydroxybenzoyl-tri-O-methylnorbergenin
  参考文献：
  名称：

  Synthesis, antioxidant capacity, and structure–activity relationships of tri-O-methylnorbergenin analogues on tyrosinase inhibition

  摘要：

  A series of tri-O-methylnorbergenin analogues 1-9 were synthesized and their antioxidant activities and inhibitory effects on tyrosinase were evaluated. Among tested analogues, compound 4 bearing cathechol moiety exhibited greater antioxidant activity and excellent inhibition on tyrosinase with IC50 value of 9.1 mu M, comparable to that of corresponding positive controls. The inhibition mechanism analysis of compound 4 demonstrated that it was a mixed-type inhibitor on tyrosinase. These results suggest that these compounds may serve as a useful clue for further designing and development of novel potential tyrosinase inhibitors. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2013.10.066

文献信息

• Synthesis, antioxidant capacity, and structure–activity relationships of tri-O-methylnorbergenin analogues on tyrosinase inhibition
  作者：Yusei Kashima、Mitsuo Miyazawa

  DOI：10.1016/j.bmcl.2013.10.066

  日期：2013.12

  A series of tri-O-methylnorbergenin analogues 1-9 were synthesized and their antioxidant activities and inhibitory effects on tyrosinase were evaluated. Among tested analogues, compound 4 bearing cathechol moiety exhibited greater antioxidant activity and excellent inhibition on tyrosinase with IC50 value of 9.1 mu M, comparable to that of corresponding positive controls. The inhibition mechanism analysis of compound 4 demonstrated that it was a mixed-type inhibitor on tyrosinase. These results suggest that these compounds may serve as a useful clue for further designing and development of novel potential tyrosinase inhibitors. (C) 2013 Elsevier Ltd. All rights reserved.