(+)-muqubilone B methyl ester | 1108199-23-0

• 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: (+)-muqubilone B methyl ester
• 英文别名: methyl (2R)-2-[(3R,6R)-6-methyl-6-[(E)-4,8,8-trimethyl-7,12-dioxotridec-3-enyl]dioxan-3-yl]propanoate
• CAS: 1108199-23-0
• 化学式: C₂₅H₄₂O₆
• 分子量: 438.605
• InChiKey: RLNZNXBQJCWOKE-VPJHOPBLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.4
• 重原子数：
  31
• 可旋转键数：
  14
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.8
• 拓扑面积：
  78.9
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  (+)-muqubilone B methyl ester 在 palladium on activated charcoal 、 氢气 作用下， 以 乙醇 为溶剂， 20.0 ℃ 、101.33 kPa 条件下， 反应 1.0h， 以4 mg的产率得到(+)-Muqubilone B Diol
  参考文献：
  名称：

  The Marine Sponge Diacarnus bismarckensis as a Source of Peroxiterpene Inhibitors of Trypanosoma brucei, the Causative Agent of Sleeping Sickness

  摘要：

  Human African trypanosomiasis, also known as African sleeping sickness, is a neglected tropical disease with inadequate therapeutic options. We have launched a collaborative new lead discovery venture using our repository of extracts and natural product compounds as input into our growth inhibition primary screen against Trypanosoma brucei. Careful evaluation of the spectral data of the natural products and derivatives allowed for the elucidation of the absolute configuration (using the modified Mosher's method) of two new peroxiterpenes: (+)-muqubilone B (1a) and (-)-ent-muqubilone (3a). Five known compounds were also isolated: (+)-sigmosceptrellin A (4a), (+)-sigmosceptrellin A methyl ester (4b), (-)-sigmosceptrellin B (5), (+)-epi-muqubillin A (6), and (-)-epi-nuapapuin B methyl ester (7). The isolated peroxiterpenes demonstrated activities in the range IC50 = 0.2-2 mu g/mL.

  DOI：

  10.1021/np800711a
• 作为产物：
  描述：

  (+)-muqubilone B 、 三甲基硅烷化重氮甲烷 以 甲醇 、 正己烷 为溶剂， 反应 0.5h， 以6.2 mg的产率得到(+)-muqubilone B methyl ester
  参考文献：
  名称：

  The Marine Sponge Diacarnus bismarckensis as a Source of Peroxiterpene Inhibitors of Trypanosoma brucei, the Causative Agent of Sleeping Sickness

  摘要：

  Human African trypanosomiasis, also known as African sleeping sickness, is a neglected tropical disease with inadequate therapeutic options. We have launched a collaborative new lead discovery venture using our repository of extracts and natural product compounds as input into our growth inhibition primary screen against Trypanosoma brucei. Careful evaluation of the spectral data of the natural products and derivatives allowed for the elucidation of the absolute configuration (using the modified Mosher's method) of two new peroxiterpenes: (+)-muqubilone B (1a) and (-)-ent-muqubilone (3a). Five known compounds were also isolated: (+)-sigmosceptrellin A (4a), (+)-sigmosceptrellin A methyl ester (4b), (-)-sigmosceptrellin B (5), (+)-epi-muqubillin A (6), and (-)-epi-nuapapuin B methyl ester (7). The isolated peroxiterpenes demonstrated activities in the range IC50 = 0.2-2 mu g/mL.

  DOI：

  10.1021/np800711a