4a-O-(benzotriazol-1-yl) 2-O-methyl (2S,4aR,6aR,6aS,6bR,8aR,9R,10R,11S,12aR,14bS)-10-[(2S,3R,4R,5R)-3,4-dihydroxy-5-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyoxan-2-yl]oxy-11-hydroxy-9-(hydroxymethyl)-2,6a,6b,9,12a-pentamethyl-1,3,4,5,6,6a,7,8,8a,10,11,12,13,14b-tetradecahydropicene-2,4a-dicarboxylate | 1000393-44-1

• 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: 4a-O-(benzotriazol-1-yl) 2-O-methyl (2S,4aR,6aR,6aS,6bR,8aR,9R,10R,11S,12aR,14bS)-10-[(2S,3R,4R,5R)-3,4-dihydroxy-5-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyoxan-2-yl]oxy-11-hydroxy-9-(hydroxymethyl)-2,6a,6b,9,12a-pentamethyl-1,3,4,5,6,6a,7,8,8a,10,11,12,13,14b-tetradecahydropicene-2,4a-dicarboxylate
• CAS: 1000393-44-1
• 化学式: C₄₈H₆₉N₃O₁₆
• 分子量: 944.086
• InChiKey: DIXJDTVJVLYROU-PEFFOWBFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  67
• 可旋转键数：
  11
• 环数：
  9.0
• sp3杂化的碳原子比例：
  0.79
• 拓扑面积：
  282
• 氢给体数：
  8
• 氢受体数：
  18

反应信息

• 作为产物：
  描述：

  1-羟基苯并三唑 、 商陆皂苷甲 在 N,N'-二环己基碳二亚胺 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 1.0h， 以63%的产率得到4a-O-(benzotriazol-1-yl) 2-O-methyl (2S,4aR,6aR,6aS,6bR,8aR,9R,10R,11S,12aR,14bS)-10-[(2S,3R,4R,5R)-3,4-dihydroxy-5-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyoxan-2-yl]oxy-11-hydroxy-9-(hydroxymethyl)-2,6a,6b,9,12a-pentamethyl-1,3,4,5,6,6a,7,8,8a,10,11,12,13,14b-tetradecahydropicene-2,4a-dicarboxylate
  参考文献：
  名称：

  Synthesis, in vitro inhibitory activity towards COX-2 and haemolytic activity of derivatives of Esculentoside A

  摘要：

  Esculentoside A (EsA) has been reported to possess anti-inflammatory activity and selective inhibitory activity towards cyclooxygenase-2. A series of derivatives of EsA were synthesized by converting the C-28 carboxylic acid group into amides. The haemolytic activity and inhibitory activity towards cyclooxygenase-2 were evaluated in vitro. The SAR study of the derivatives was conducted and showed that introducing aromatic ring to EsA greatly enhanced its biological activity. Compound 23 showed higher inhibitory activity than Celecoxib and EsA, but lower haemolytic toxicity than EsA. (c) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2007.10.006

文献信息

• Synthesis, in vitro inhibitory activity towards COX-2 and haemolytic activity of derivatives of Esculentoside A
  作者：Fei Wu、Yanghua Yi、Peng Sun、Dazhi Zhang

  DOI：10.1016/j.bmcl.2007.10.006

  日期：2007.12

  Esculentoside A (EsA) has been reported to possess anti-inflammatory activity and selective inhibitory activity towards cyclooxygenase-2. A series of derivatives of EsA were synthesized by converting the C-28 carboxylic acid group into amides. The haemolytic activity and inhibitory activity towards cyclooxygenase-2 were evaluated in vitro. The SAR study of the derivatives was conducted and showed that introducing aromatic ring to EsA greatly enhanced its biological activity. Compound 23 showed higher inhibitory activity than Celecoxib and EsA, but lower haemolytic toxicity than EsA. (c) 2007 Elsevier Ltd. All rights reserved.