((1R,2R,4aS,5R,8aS)-2-hydroxyl-5-((E)-2-((S)-4-hydroxyl-2-oxodihydrofuran-3(2H)-ylidene)ethyl)-1,4a-dimethyl-6-methylenedecahydronaphthalen-1-yl)methyl 2,4,6-trimethylbenzenesulfonate

• 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: ((1R,2R,4aS,5R,8aS)-2-hydroxyl-5-((E)-2-((S)-4-hydroxyl-2-oxodihydrofuran-3(2H)-ylidene)ethyl)-1,4a-dimethyl-6-methylenedecahydronaphthalen-1-yl)methyl 2,4,6-trimethylbenzenesulfonate
• 英文别名: [(1R,2R,4aS,5R,8aS)-2-hydroxy-5-[(2E)-2-[(4S)-4-hydroxy-2-oxooxolan-3-ylidene]ethyl]-1,4a-dimethyl-6-methylidene-3,4,5,7,8,8a-hexahydro-2H-naphthalen-1-yl]methyl 2,4,6-trimethylbenzenesulfonate
• 化学式: C₂₉H₄₀O₇S
• 分子量: 532.698
• InChiKey: MOTCXEPFTZUFTL-MJSWAYRLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.3
• 重原子数：
  37.0
• 可旋转键数：
  6.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.62
• 拓扑面积：
  110.13
• 氢给体数：
  2.0
• 氢受体数：
  7.0

反应信息

• 作为产物：
  描述：

  穿心莲内酯 在 吡啶 、 盐酸 、 碘 、 sodium methylate 作用下， 以 四氢呋喃 、 甲醇 、 水 为溶剂， 反应 11.0h， 生成 ((1R,2R,4aS,5R,8aS)-2-hydroxyl-5-((E)-2-((S)-4-hydroxyl-2-oxodihydrofuran-3(2H)-ylidene)ethyl)-1,4a-dimethyl-6-methylenedecahydronaphthalen-1-yl)methyl 2,4,6-trimethylbenzenesulfonate
  参考文献：
  名称：

  Synthesis of new andrographolide derivatives and evaluation of their antidyslipidemic, LDL-oxidation and antioxidant activity

  摘要：

  Andrographis paniculata, native to Taiwan, Mainland China and India, is a medicinal herb, which possesses various biological activities including anti-atherosclerosis. Andrographolide (1) has been identified as one of the active constituents against atherosclerosis. In continuation of our drug discovery program we synthesized few novel derivatives of 1 to improve their antidyslipidemic, LDL-oxidation and antioxidant activity. The tosylated derivative 7 has been turned out to be more potent than the parent compound and comparable activity with marketed antidyslipidemic drugs. (C) 2013 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2013.09.002

文献信息

• Synthesis of new andrographolide derivatives and evaluation of their antidyslipidemic, LDL-oxidation and antioxidant activity
  作者：Sukanya Pandeti、Ravi Sonkar、Astha Shukla、Gitika Bhatia、Narender Tadigoppula

  DOI：10.1016/j.ejmech.2013.09.002

  日期：2013.11

  Andrographis paniculata, native to Taiwan, Mainland China and India, is a medicinal herb, which possesses various biological activities including anti-atherosclerosis. Andrographolide (1) has been identified as one of the active constituents against atherosclerosis. In continuation of our drug discovery program we synthesized few novel derivatives of 1 to improve their antidyslipidemic, LDL-oxidation and antioxidant activity. The tosylated derivative 7 has been turned out to be more potent than the parent compound and comparable activity with marketed antidyslipidemic drugs. (C) 2013 Elsevier Masson SAS. All rights reserved.