(4S,E)-4-hydroxy-3-(2-((1R,4aS,5R, 6R,8aS)-6-hydroxy-5-(hydroxymethyl)-2,5,8a-trimethyldecahydronaphthalen-1-yl) ethylidene)dihydrofuran-2(3H)-one

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 内酯类
• 英文名称: (4S,E)-4-hydroxy-3-(2-((1R,4aS,5R, 6R,8aS)-6-hydroxy-5-(hydroxymethyl)-2,5,8a-trimethyldecahydronaphthalen-1-yl) ethylidene)dihydrofuran-2(3H)-one
• 英文别名: (3E,4S)-3-[2-[(1R,4aS,5R,6R,8aS)-6-hydroxy-5-(hydroxymethyl)-2,5,8a-trimethyl-1,2,3,4,4a,6,7,8-octahydronaphthalen-1-yl]ethylidene]-4-hydroxyoxolan-2-one
• 化学式: C₂₀H₃₂O₅
• 分子量: 352.471
• InChiKey: ARUWGSPXMHTGRX-LKSVVPNCSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.04
• 重原子数：
  25.0
• 可旋转键数：
  3.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.85
• 拓扑面积：
  86.99
• 氢给体数：
  3.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  (4S,E)-4-hydroxy-3-(2-((1R,4aS,5R, 6R,8aS)-6-hydroxy-5-(hydroxymethyl)-2,5,8a-trimethyldecahydronaphthalen-1-yl) ethylidene)dihydrofuran-2(3H)-one 在 sodium tetrahydroborate 、 nickel(II) chloride hexahydrate 作用下， 以 甲醇 为溶剂， 反应 0.5h， 以90%的产率得到(4S)-4-hydroxy-3-(2-((1R,4aS,5R, 6R, 8aS)-6-hydroxy-5-(hydroxymethyl)-2,5,8a-trimethyldecahydronaphthalen-1-yl) ethyl)dihydrofuran-2(3H)-one
  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 palladium 10% on activated carbon 、 氢气 作用下， 以 甲醇 为溶剂， 反应 1.0h， 以90%的产率得到(4S,E)-4-hydroxy-3-(2-((1R,4aS,5R, 6R,8aS)-6-hydroxy-5-(hydroxymethyl)-2,5,8a-trimethyldecahydronaphthalen-1-yl) ethylidene)dihydrofuran-2(3H)-one
  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