1-O-isobutyrylnigericinol | 138285-71-9

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 1-O-isobutyrylnigericinol
• 英文别名: [(2S)-2-[(2R,3S,6R)-6-[[(2S,4R,6R,7R,9R)-2-[(2R,5S)-5-[(2R,3S,5R)-5-[(2S,3S,5R,6R)-6-hydroxy-6-(hydroxymethyl)-3,5-dimethyloxan-2-yl]-3-methyloxolan-2-yl]-5-methyloxolan-2-yl]-7-methoxy-2,4,6-trimethyl-1,10-dioxaspiro[4.5]decan-9-yl]methyl]-3-methyloxan-2-yl]propyl] 2-methylpropanoate
• CAS: 138285-71-9
• 化学式: C₄₄H₇₆O₁₁
• 分子量: 781.081
• InChiKey: SGGCZDHBPWBFHJ-XNNPZDAWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.2
• 重原子数：
  55
• 可旋转键数：
  12
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.98
• 拓扑面积：
  131
• 氢给体数：
  2
• 氢受体数：
  11

反应信息

• 作为产物：
  描述：

  在 四丁基氟化铵 作用下， 以 四氢呋喃 为溶剂， 反应 6.0h， 以72%的产率得到1-O-isobutyrylnigericinol
  参考文献：
  名称：

  Secondary metabolites by chemical screening. 17. Nigericinol derivatives: synthesis, biological activities and modeling studies

  摘要：

  The synthesis and the biological activity of C-1-reduced nigericin derivatives (nigericinols) are described and discussed. The dichloronigericinol 7 impressively demonstrated that the C-1 carboxylic acid moiety was not required for a distinct activity against bacteria and viruses. Based on the correlation between K+/H+ antiport activities and antibacterial activities it was deduced that the mode of action of the described nigericinols are related to their ionophoric properties. Molecular modeling studies showed that the efficiency of the nigericinols as ionophores correlates, qualitatively, with the probability of forming a cyclic structure, with the exception of 7.

  DOI：

  10.1021/jm00083a020