30-O-isobutyryl-29-O-methylnigericin | 138285-66-2

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 30-O-isobutyryl-29-O-methylnigericin
• 英文别名: (2R)-2-[(2R,3S,6R)-6-[[(2S,4R,6R,7R,9R)-7-methoxy-2-[(2R,5S)-5-[(2R,3S,5R)-5-[(2S,3S,5R,6R)-6-methoxy-3,5-dimethyl-6-(2-methylpropanoyloxymethyl)oxan-2-yl]-3-methyloxolan-2-yl]-5-methyloxolan-2-yl]-2,4,6-trimethyl-1,10-dioxaspiro[4.5]decan-9-yl]methyl]-3-methyloxan-2-yl]propanoic acid
• CAS: 138285-66-2
• 化学式: C₄₅H₇₆O₁₂
• 分子量: 809.091
• InChiKey: IROZJDKUPXNCCQ-KLQHEOLQSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.7
• 重原子数：
  57
• 可旋转键数：
  13
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.96
• 拓扑面积：
  137
• 氢给体数：
  1
• 氢受体数：
  12

反应信息

• 作为反应物：
  描述：

  30-O-isobutyryl-29-O-methylnigericin 在 sodium tetrahydroborate 、 水 、 三氯化铁 、 N,N'-羰基二咪唑 作用下， 以 异丙醇 为溶剂， 反应 11.0h， 生成 30-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
• 作为产物：
  描述：

  nigericin 在 吡啶 、 lithium bromide 作用下， 反应 32.0h， 生成 30-O-isobutyryl-29-O-methylnigericin
  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

文献信息

• Secondary metabolites by chemical screening. 17. Nigericinol derivatives: synthesis, biological activities and modeling studies
  作者：Susanne Grabley、Peter Hammann、Robert Klein、Gerhard Seibert、Irvin Winkler、Achim Kroeger、Frank Ditzel

  DOI：10.1021/jm00083a020

  日期：1992.3

  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.