(S,E)-4-(2-((1R,4aS,5R,6R,8aS)-6-hydroxyl-5-((mesitylsulfonyloxy)methyl)-5,8a-dimethyl-2-methylene decahydronaphthalen-1-yl)ethylidene)-5-oxotetrahydrofuran-3-yl acetate

• 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: (S,E)-4-(2-((1R,4aS,5R,6R,8aS)-6-hydroxyl-5-((mesitylsulfonyloxy)methyl)-5,8a-dimethyl-2-methylene decahydronaphthalen-1-yl)ethylidene)-5-oxotetrahydrofuran-3-yl acetate
• 英文别名: [(3S,4E)-4-[2-[(1R,4aS,5R,6R,8aS)-6-hydroxy-5,8a-dimethyl-2-methylidene-5-[(2,4,6-trimethylphenyl)sulfonyloxymethyl]-3,4,4a,6,7,8-hexahydro-1H-naphthalen-1-yl]ethylidene]-5-oxooxolan-3-yl] acetate
• 化学式: C₃₁H₄₂O₈S
• 分子量: 574.736
• InChiKey: HMXIPGNRYJRAED-OZEOGBFXSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.87
• 重原子数：
  40.0
• 可旋转键数：
  7.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.61
• 拓扑面积：
  116.2
• 氢给体数：
  1.0
• 氢受体数：
  8.0

反应信息

• 作为反应物：
  描述：

  (S,E)-4-(2-((1R,4aS,5R,6R,8aS)-6-hydroxyl-5-((mesitylsulfonyloxy)methyl)-5,8a-dimethyl-2-methylene decahydronaphthalen-1-yl)ethylidene)-5-oxotetrahydrofuran-3-yl acetate 在 sodium methylate 作用下， 以 甲醇 为溶剂， 反应 1.0h， 以85%的产率得到((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
• 作为产物：
  描述：

  穿心莲内酯 在 吡啶 、 盐酸 、 碘 作用下， 以 四氢呋喃 、 水 为溶剂， 反应 10.0h， 生成 (S,E)-4-(2-((1R,4aS,5R,6R,8aS)-6-hydroxyl-5-((mesitylsulfonyloxy)methyl)-5,8a-dimethyl-2-methylene decahydronaphthalen-1-yl)ethylidene)-5-oxotetrahydrofuran-3-yl acetate
  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.