[(2R,3S,6S,7R,8R)-8-benzyl-2,6-dimethyl-4,9-dioxo-3-[[3-[[(2S)-3,3,3-trifluoro-2-methoxy-2-phenylpropanoyl]amino]-2-[(2S)-3,3,3-trifluoro-2-methoxy-2-phenylpropanoyl]oxybenzoyl]amino]-1,5-dioxonan-7-yl] (2S)-3,3,3-trifluoro-2-methoxy-2-phenylpropanoate | 1148106-28-8

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: [(2R,3S,6S,7R,8R)-8-benzyl-2,6-dimethyl-4,9-dioxo-3-[[3-[[(2S)-3,3,3-trifluoro-2-methoxy-2-phenylpropanoyl]amino]-2-[(2S)-3,3,3-trifluoro-2-methoxy-2-phenylpropanoyl]oxybenzoyl]amino]-1,5-dioxonan-7-yl] (2S)-3,3,3-trifluoro-2-methoxy-2-phenylpropanoate
• CAS: 1148106-28-8
• 化学式: C₅₃H₄₇F₉N₂O₁₃
• 分子量: 1090.95
• InChiKey: YKSGNRORSHSEQS-ZOOUUQEWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  10
• 重原子数：
  77
• 可旋转键数：
  18
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.32
• 拓扑面积：
  191
• 氢给体数：
  2
• 氢受体数：
  22

反应信息

• 作为产物：
  描述：

  [2-[[(2R,3S,6S,7R,8R)-8-benzyl-7-hydroxy-2,6-dimethyl-4,9-dioxo-1,5-dioxonan-3-yl]carbamoyl]-6-[[(2S)-3,3,3-trifluoro-2-methoxy-2-phenylpropanoyl]amino]phenyl] (2S)-3,3,3-trifluoro-2-methoxy-2-phenylpropanoate 、 (R)-methoxytrifluoromethylphenylacetyl chloride 在 4-二甲氨基吡啶 作用下， 以 吡啶 为溶剂， 生成 [(2R,3S,6S,7R,8R)-8-benzyl-2,6-dimethyl-4,9-dioxo-3-[[3-[[(2S)-3,3,3-trifluoro-2-methoxy-2-phenylpropanoyl]amino]-2-[(2S)-3,3,3-trifluoro-2-methoxy-2-phenylpropanoyl]oxybenzoyl]amino]-1,5-dioxonan-7-yl] (2S)-3,3,3-trifluoro-2-methoxy-2-phenylpropanoate
  参考文献：
  名称：

  Potent Inhibitors of Pro-Inflammatory Cytokine Production Produced by a Marine-Derived Bacterium

  摘要：

  Cytokines produced through the antigen presenting cell (APC)-T-cell interaction play a key role in the activation of the allergic asthmatic response. Evaluating small molecules that inhibit the production of these pro-inflammatory proteins is therefore important for the discovery of novel chemical structures with potential antiasthma activity. We adapted a mouse splerrocyte cytokine assay to screen a library of 2,500 marine microbial extracts for their ability to inhibit T(H)2 cytokine release and identified potent activity in a marine-derived strain CNQ431, identified as a Streptomyces species. Bioactivity guided fractionation of the organic extract of this strain led to the isolation of ten new 9-membered bis-lactones, splenocins A-J (1-10). The new compounds display potent biological activities, comparable to that of the corticosteroid dexamethasone, with IC50 values from 2 to 50 nM in the splenocyte cytokine assay. This study provides the foundation for the optimization of these potent anti-inflammatory compounds for development in the treatment of asthma.

  DOI：

  10.1021/jm801110j