14-deoxy-11,12-didehydro-3,19-dinicotinoylandrographolide | 943430-82-8

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 异戊烯醇脂质
• 英文名称: 14-deoxy-11,12-didehydro-3,19-dinicotinoylandrographolide
• 英文别名: [(1R,2R,4aR,5R,8aS)-1,4a-dimethyl-6-methylidene-5-[(E)-2-(5-oxo-2H-furan-4-yl)ethenyl]-2-(pyridine-3-carbonyloxy)-3,4,5,7,8,8a-hexahydro-2H-naphthalen-1-yl]methyl pyridine-3-carboxylate
• CAS: 943430-82-8
• 化学式: C₃₂H₃₄N₂O₆
• 分子量: 542.632
• InChiKey: JHXNJJHWXFHMIC-JQBVRJHYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5
• 重原子数：
  40
• 可旋转键数：
  9
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.41
• 拓扑面积：
  105
• 氢给体数：
  0
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  14-deoxy-11,12-didehydro-3,19-dinicotinoylandrographolide 、 柠檬醛 在 sodium carbonate 作用下， 以 甲醇 为溶剂， 生成 14-deoxy-11,12-didehydro-3,19-dinicotinoyl-15-(2,8-dimethanyl-2,7-octanedienylidene)andrographolide
  参考文献：
  名称：

  Synthesis of andrographolide derivatives: A new family of α-glucosidase inhibitors

  摘要：

  Andrographolide (1), the cytotoxic agent of the plant Andrographis paniculata, was subjected to semi-synthetic studies leading to a series of new derivatives, a novel family of glucosidase inhibitors. Nicotination of 3,19-hydroxyls in 15-alkylidene andrographolide derivatives (9) was favorable to alpha-glucosidase inhibition activity. Among them, 15-p-chlorobenzylidene-14-deoxy-11,12-didehydro-3,19-dinicotinateandrographolide (11c) was a very potent inhibitor against alpha-glucosidase with an IC50 value of 6 mu M. However, all compounds concerned for beta-glucosidase showed no inhibition. All compounds synthesized were characterized by the analysis of NMR, IR, HRMS spectra and the stereochemistry of 2 was confirmed by X-ray analysis. (C) 2007 Published by Elsevier Ltd.

  DOI：

  10.1016/j.bmc.2007.03.063
• 作为产物：
  描述：

  烟酰氯 、 14-去氧-11,12-二去氢穿心莲内酯 在 三乙胺 作用下， 以 氯仿 为溶剂， 反应 3.0h， 以92%的产率得到14-deoxy-11,12-didehydro-3,19-dinicotinoylandrographolide
  参考文献：
  名称：

  Synthesis of andrographolide derivatives: A new family of α-glucosidase inhibitors

  摘要：

  Andrographolide (1), the cytotoxic agent of the plant Andrographis paniculata, was subjected to semi-synthetic studies leading to a series of new derivatives, a novel family of glucosidase inhibitors. Nicotination of 3,19-hydroxyls in 15-alkylidene andrographolide derivatives (9) was favorable to alpha-glucosidase inhibition activity. Among them, 15-p-chlorobenzylidene-14-deoxy-11,12-didehydro-3,19-dinicotinateandrographolide (11c) was a very potent inhibitor against alpha-glucosidase with an IC50 value of 6 mu M. However, all compounds concerned for beta-glucosidase showed no inhibition. All compounds synthesized were characterized by the analysis of NMR, IR, HRMS spectra and the stereochemistry of 2 was confirmed by X-ray analysis. (C) 2007 Published by Elsevier Ltd.

  DOI：

  10.1016/j.bmc.2007.03.063

文献信息

• Synthesis of andrographolide derivatives: A new family of α-glucosidase inhibitors
  作者：Hai-Wei Xu、Gui-Fu Dai、Gai-Zhi Liu、Jun-Feng Wang、Hong-Min Liu

  DOI：10.1016/j.bmc.2007.03.063

  日期：2007.6

  Andrographolide (1), the cytotoxic agent of the plant Andrographis paniculata, was subjected to semi-synthetic studies leading to a series of new derivatives, a novel family of glucosidase inhibitors. Nicotination of 3,19-hydroxyls in 15-alkylidene andrographolide derivatives (9) was favorable to alpha-glucosidase inhibition activity. Among them, 15-p-chlorobenzylidene-14-deoxy-11,12-didehydro-3,19-dinicotinateandrographolide (11c) was a very potent inhibitor against alpha-glucosidase with an IC50 value of 6 mu M. However, all compounds concerned for beta-glucosidase showed no inhibition. All compounds synthesized were characterized by the analysis of NMR, IR, HRMS spectra and the stereochemistry of 2 was confirmed by X-ray analysis. (C) 2007 Published by Elsevier Ltd.