鸦胆子素B | 25514-29-8

• 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
• 中文名称: 鸦胆子素B
• 英文名称: bruceine B
• 英文别名: methyl (1R,2S,3R,6R,8R,13S,14R,15R,16S,17S)-3-acetyloxy-10,15,16-trihydroxy-9,13-dimethyl-4,11-dioxo-5,18-dioxapentacyclo[12.5.0.01,6.02,17.08,13]nonadec-9-ene-17-carboxylate
• CAS: 25514-29-8
• 化学式: C₂₃H₂₈O₁₁
• 分子量: 480.469
• InChiKey: YDWODLQEUPYKGJ-LZFWDZGBSA-N

物化性质

• 沸点：
  701.8±60.0 °C(Predicted)
• 密度：
  1.52±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -0.5
• 重原子数：
  34
• 可旋转键数：
  4
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.74
• 拓扑面积：
  166
• 氢给体数：
  3
• 氢受体数：
  11

制备方法与用途

化学性质
这是一种白色结晶性粉末，能够溶解在甲醇、乙醇和DMSO等有机溶剂中，源自鸦胆子果实。

用途
鸦胆子素B具有治疗恶性肿瘤、抗疟疾以及抗炎的多种作用。

反应信息

• 作为产物：
  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 6.5h， 生成 鸦胆子素B
  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

文献信息

• New Semisynthetic Quassinoids with in Vivo Antimalarial Activity
  作者：Nobutoshi Murakami、Masanori Sugimoto、Motoyuki Kawanishi、Satoru Tamura、Hye-Sook Kim、Khurshida Begum、Yusuke Wataya、Motomasa Kobayashi

  DOI：10.1021/jm0201971

  日期：2003.2.1

  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.