3-O-triethylsilylbruceolide | 205655-77-2

• 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: 3-O-triethylsilylbruceolide
• 英文别名: methyl (1R,2S,3R,6R,8R,13S,14R,15R,16S,17S)-3,15,16-trihydroxy-9,13-dimethyl-4,11-dioxo-10-triethylsilyloxy-5,18-dioxapentacyclo[12.5.0.01,6.02,17.08,13]nonadec-9-ene-17-carboxylate
• CAS: 205655-77-2
• 化学式: C₂₇H₄₀O₁₀Si
• 分子量: 552.694
• InChiKey: RESQRFDCERTIEB-LXQJQWFWSA-N

物化性质

• 沸点：
  671.9±55.0 °C(Predicted)
• 密度：
  1.32±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.46
• 重原子数：
  38
• 可旋转键数：
  7
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.81
• 拓扑面积：
  149
• 氢给体数：
  3
• 氢受体数：
  10

反应信息

• 作为反应物：
  描述：

  3-O-triethylsilylbruceolide 在 吡啶 、 氟化氢吡啶 作用下， 以 四氢呋喃 为溶剂， 反应 5.0h， 生成 methyl (1R,2S,3R,6R,8R,13S,14R,15R,16S,17S)-10,15,16-trihydroxy-3-methoxycarbonyloxy-9,13-dimethyl-4,11-dioxo-5,18-dioxapentacyclo[12.5.0.01,6.02,17.08,13]nonadec-9-ene-17-carboxylate
  参考文献：
  名称：

  New Semisynthetic Quassinoids with in Vivo Antimalarial Activity

  摘要：

  On the basis of a comparative analysis for stability in mouse serum between 15-O-acetylbruceolide and bruceolide 15-methyl carbonate, several 3,15-dialkyl carbonates of bruceolide were synthesized and their in vitro antimalarial activity was assessed. Methyl, ethyl, and isopropyl carbonates with pronounced in vitro activity were further evaluated for in vivo antimalarial potency. Both the methyl and ethyl carbonates significantly increased the life span of mice as compared with 3,15-di-O-accetylbruceolide and chloroquine.

  DOI：

  10.1021/jm0201971
• 作为产物：
  描述：

  deacetylyadanzioside F 在 吡啶 、 acetate buffer 、 celluase from Aspergillus niger 作用下， 生成 3-O-triethylsilylbruceolide
  参考文献：
  名称：

  Anti-malarial activities of acylated bruceolide derivatives

  摘要：

  Several O-acylated derivatives of bruceolide (2) were synthesized and their anti-malarial activities together with selective toxicities were examined. It was found that 3,15-di-O-acetyl- (3c), 3,15-di-O-propionyl- (3d) and 15-O-propionylbruceolide (3b), as well as bruceine B (3a), exhibited potent anti-malarial activities with high selective toxicities. (C) 1998 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(98)00045-6