(20S,24S)-epoxy-3β-O-acetyl-25-hydroxydammarane-12-one | 1469999-09-4

• 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: (20S,24S)-epoxy-3β-O-acetyl-25-hydroxydammarane-12-one
• 英文别名: [(3S,5R,8R,9R,10R,13R,14R,17S)-17-[(2S,5S)-5-(2-hydroxypropan-2-yl)-2-methyloxolan-2-yl]-4,4,8,10,14-pentamethyl-12-oxo-1,2,3,5,6,7,9,11,13,15,16,17-dodecahydrocyclopenta[a]phenanthren-3-yl] acetate
• CAS: 1469999-09-4
• 化学式: C₃₂H₅₂O₅
• 分子量: 516.762
• InChiKey: XPNOOZBVQYGHTA-RDHUZIRASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.2
• 重原子数：
  37
• 可旋转键数：
  4
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.94
• 拓扑面积：
  72.8
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (20S,24S)-epoxy-3β-O-acetyl-25-hydroxydammarane-12-one 在 甲醇 、 potassium hydroxide 作用下， 反应 5.0h， 以87%的产率得到(20S,24S)-epoxy-3β,25-dihydroxydammarane-12-one
  参考文献：
  名称：

  Synthesis and biological evaluation of novel ocotillol-type triterpenoid derivatives as antibacterial agents

  摘要：

  A novel class of ocotillol-type triterpenoid derivatives have been synthesized and evaluated for their in vitro antibacterial activity against several representative pathogenic bacterial strains. Compounds 20(S)-protopanaxadiol (PPD), 3, 5,16 and 24 exhibited potent antibacterial activity against Gram-positive bacteria. Compounds 3 and 5 also displayed promising antibacterial activity against a community-associated methicillin-resistant Staphylococcus aureus (CA-MRSA; strain USA300). Furthermore, compounds PPD, 3 and 16 combined with two commercially available antibiotics kanamycin and chloramphenicol showed strong synergistic inhibitory effects at their sub-MIC concentrations against S. aureus USA300 and Bacillus subtilis 168. Additionally, cytotoxic activity assay showed that the compounds tested did not affect cell viability of the human epithelial kidney (HEK-293) and human cervical (HeLa) cells at their MICs. (C) 2013 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2013.07.041
• 作为产物：
  描述：

  原人参二醇 在 吡啶 、 甲醇 、 4-二甲氨基吡啶 、 间氯过氧苯甲酸 、 pyridinium chlorochromate 、 potassium hydroxide 作用下， 以 二氯甲烷 为溶剂， 反应 50.0h， 生成 (20S,24S)-epoxy-3β-O-acetyl-25-hydroxydammarane-12-one
  参考文献：
  名称：

  Synthesis and biological evaluation of novel ocotillol-type triterpenoid derivatives as antibacterial agents

  摘要：

  A novel class of ocotillol-type triterpenoid derivatives have been synthesized and evaluated for their in vitro antibacterial activity against several representative pathogenic bacterial strains. Compounds 20(S)-protopanaxadiol (PPD), 3, 5,16 and 24 exhibited potent antibacterial activity against Gram-positive bacteria. Compounds 3 and 5 also displayed promising antibacterial activity against a community-associated methicillin-resistant Staphylococcus aureus (CA-MRSA; strain USA300). Furthermore, compounds PPD, 3 and 16 combined with two commercially available antibiotics kanamycin and chloramphenicol showed strong synergistic inhibitory effects at their sub-MIC concentrations against S. aureus USA300 and Bacillus subtilis 168. Additionally, cytotoxic activity assay showed that the compounds tested did not affect cell viability of the human epithelial kidney (HEK-293) and human cervical (HeLa) cells at their MICs. (C) 2013 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2013.07.041