3,19-p-methoxybenzylidene andrographolide

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 类固醇和类固醇衍生物
• 英文名称: 3,19-p-methoxybenzylidene andrographolide
• 英文别名: (3E,4S)-3-[2-[(4aR,6aS,7R,10aS,10bR)-3-(4-methoxyphenyl)-6a,10b-dimethyl-8-methylidene-1,4a,5,6,7,9,10,10a-octahydronaphtho[2,1-d][1,3]dioxin-7-yl]ethylidene]-4-hydroxyoxolan-2-one
• 化学式: C₂₈H₃₆O₆
• 分子量: 468.59
• InChiKey: GGQLCHJDKBKVJS-PHQQLAFWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.1
• 重原子数：
  34
• 可旋转键数：
  4
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.61
• 拓扑面积：
  74.2
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  4-甲氧基苯甲醛二甲缩醛 、 穿心莲内酯 在 camphor-10-sulfonic acid 作用下， 以 N,N-二甲基甲酰胺 、 甲苯 为溶剂， 以95%的产率得到3,19-p-methoxybenzylidene andrographolide
  参考文献：
  名称：

  樟脑磺酸介导的从穿心莲中分离出的主要Labdane二萜类化合物具有定量的1,3-二醇保护作用。

  摘要：

  穿心莲干燥部位甲醇提取物的植物化学调查导致分离出主要的拉丹烷二萜，即14-脱氧-11,12-二氢加氢穿心莲内酯，穿心莲内酯和新穿心莲内酯。发现穿心莲内酯是具有生物活性的植物的主要植物成分。为了获得更好的理化特性和生物功效，穿心莲内酯经过半合成修饰。然而，与该分子缔合的几个游离羟基的存在使其极性很大并且在许多有机溶剂中难溶，因此不适合合成修饰。解决其溶解度问题的一种方法是在温和的反应条件下定量保护1,3-二醇而不会影响其他官能团。使用不同的溶剂系统和催化剂朝这个方向优化反应条件。X射线结构为3，本文首次报道了19-异亚丙基-14-脱氧-11,12-二氢穿心莲内酯。通过光谱分析或X射线数据分析确认了分离的化合物和衍生物。

  DOI：

  10.1080/14786419.2017.1402313

文献信息

• Studies on the novel α-glucosidase inhibitory activity and structure–activity relationships for andrographolide analogues
  作者：Gui-Fu Dai、Hai-Wei Xu、Jun-Feng Wang、Feng-Wu Liu、Hong-Min Liu

  DOI：10.1016/j.bmcl.2006.02.011

  日期：2006.5

  A series of analogues of andrographolide were synthesized and evaluated as novel alpha-glucosidase inhibitors. Among them compound 23, 15-p-methoxylbenzylidene 14-deoxy-11, 12-didehydroandrographolide, was a potent inhibitor against alpha-glucosidase Whose IC50 value was 16 mu M. The structure-activity relationships were also discussed. (C) 2006 Elsevier Ltd. All rights reserved.
• 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.