(20S,24S)-epoxy-3β-O-acetyl-dammarane-12β,25-diol | 651025-51-3

• 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-dammarane-12β,25-diol
• 英文别名: (20S,24S)-epoxy-3β-O-acetyldammarane-12β,25-diol；(20S,24S)-3-Acetyl-20,24-epoxydammarane-3,12,25-triol；[(3S,5R,8R,9R,10R,12R,13R,14R,17S)-12-hydroxy-17-[(2S,5S)-5-(2-hydroxypropan-2-yl)-2-methyloxolan-2-yl]-4,4,8,10,14-pentamethyl-2,3,5,6,7,9,11,12,13,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-3-yl] acetate
• CAS: 651025-51-3
• 化学式: C₃₂H₅₄O₅
• 分子量: 518.778
• InChiKey: NHBJTOHJGLCSIU-CPBCUCJJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.5
• 重原子数：
  37
• 可旋转键数：
  4
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.97
• 拓扑面积：
  76
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (20S,24S)-epoxy-3β-O-acetyl-dammarane-12β,25-diol 在 甲醇 、 pyridinium chlorochromate 、 potassium hydroxide 作用下， 以 二氯甲烷 为溶剂， 反应 15.0h， 生成 (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 4-二甲氨基吡啶 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 、 间氯过氧苯甲酸 、 potassium hydroxide 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 5.0h， 生成 (20S,24S)-epoxy-3β-O-acetyl-dammarane-12β,25-diol
  参考文献：
  名称：

  Bi, Yi; Ma, Cong; Zhou, Zhiwen, Records of Natural Products, 2015, vol. 9, # 3, p. 356 - 368

  摘要：

  DOI：

文献信息

• New Dammarane Triterpenes from the Aerial Parts of <i>Ibicella lutea</i> Grown in Argentina
  作者：Mario J. Simirgiotis、Carlos Jiménez、Jaime Rodríguez、Oscar S. Giordano、Carlos E. Tonn

  DOI：10.1021/np030273i

  日期：2003.12.1

  Two new dammarane triterpenes have been isolated from the aerial parts of Ibicella lutea, 3-acetyl-24-epi-polacandrin (1) and 1,3-diacetyl-24-epi-polacandrin (2), and were obtained along with the known compounds 20S*,24S*-epoxy-3beta,12beta,25-trihydroxydammarane (3) and apigenin. The structures of compounds I and 2 were deduced by spectroscopic studies and by chemical transformations leading to the preparation of derivatives 4-11. The structure and relative stereochemistry of 1 were verified by single-crystal X-ray analysis. The natural compounds and selected semisynthetic derivatives were evaluated against several tumor cells.
• Bi, Yi; Ma, Cong; Zhou, Zhiwen, Records of Natural Products, 2015, vol. 9, # 3, p. 356 - 368
  作者：Bi, Yi、Ma, Cong、Zhou, Zhiwen、Zhang, Tingting、Zhang, Hengyuan、Zhang, Xiaochen、Lu, Jing、Meng, Qingguo、Lewis, Peter J.、Xu, Jinyi

  DOI：——

  日期：——
• Synthesis and biological evaluation of novel ocotillol-type triterpenoid derivatives as antibacterial agents
  作者：Zhiwen Zhou、Cong Ma、Hengyuan Zhang、Yi Bi、Xia Chen、Hua Tian、Xiaoni Xie、Qingguo Meng、Peter John Lewis、Jinyi Xu

  DOI：10.1016/j.ejmech.2013.07.041

  日期：2013.10

  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.