paraminabeolide D | 1289420-25-2

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 类固醇和类固醇衍生物
• 英文名称: paraminabeolide D
• 英文别名: (3R,4S,5R)-5-[(1S,2S)-2-[(8S,9S,10R,13S,14S,17R)-10,13-dimethyl-3-oxo-6,7,8,9,11,12,14,15,16,17-decahydrocyclopenta[a]phenanthren-17-yl]-1-hydroxypropyl]-3,4-dimethyloxolan-2-one
• CAS: 1289420-25-2
• 化学式: C₂₈H₄₀O₄
• 分子量: 440.623
• InChiKey: UISXVQNCBCKQHL-PPGQKZPJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.2
• 重原子数：
  32
• 可旋转键数：
  3
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.79
• 拓扑面积：
  63.6
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  paraminabeolide D 、 (R)-methoxytrifluoromethylphenylacetyl chloride 在 吡啶 作用下， 反应 3.0h， 以0.4 mg的产率得到[(1S,2S)-2-[(8S,9S,10R,13S,14S,17R)-10,13-dimethyl-3-oxo-6,7,8,9,11,12,14,15,16,17-decahydrocyclopenta[a]phenanthren-17-yl]-1-[(2R,3S,4R)-3,4-dimethyl-5-oxooxolan-2-yl]propyl] (2S)-3,3,3-trifluoro-2-methoxy-2-phenylpropanoate
  参考文献：
  名称：

  Paraminabeolides A−F, Cytotoxic and Anti-inflammatory Marine Withanolides from the Soft Coral Paraminabea acronocephala

  摘要：

  Six new withanolides, paraminabeolides A-F (1-6), along with five known compounds, minabeolides-1, -2, -4, -5, and -8 (7-11), were isolated from a Formosan soft coral, Paraminabea acronocephata. The structures of these compounds were elucidated by extensive spectroscopic analysis and chemical transformation. The absolute configuration of 4 was determined by the application of Mosher's method. Compounds 1 and 7 were cytotoxic toward Hep G2 cancer cells. Compounds 1-4 and 7-10 were found to significantly inhibit the accumulation of the pro-inflammatory iNOS protein. Compounds 7-10 also could effectively reduce the expression of COX-2 protein.

  DOI：

  10.1021/np2000705