(5β,7α,9β,10α)-7,14-dihydroxykaur-17-(4-fluorine)aniline-3,15-dione

• 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: (5β,7α,9β,10α)-7,14-dihydroxykaur-17-(4-fluorine)aniline-3,15-dione
• 英文别名: (1R,2R,4S,9R,10S,13S,16R)-14-[(4-fluoroanilino)methyl]-2,16-dihydroxy-5,5,9-trimethyltetracyclo[11.2.1.01,10.04,9]hexadecane-6,15-dione
• 化学式: C₂₆H₃₄FNO₄
• 分子量: 443.559
• InChiKey: VWMFYPKCULFESU-IMLJQXPSSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  32
• 可旋转键数：
  3
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.69
• 拓扑面积：
  86.6
• 氢给体数：
  3
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  蓝萼甲素 、 4-氟苯胺 在 silica gel 作用下， 以 甲醇 为溶剂， 以90%的产率得到(5β,7α,9β,10α)-7,14-dihydroxykaur-17-(4-fluorine)aniline-3,15-dione
  参考文献：
  名称：

  Synthesis and biological evaluation of glaucocalyxin A derivatives as potential anticancer agents

  摘要：

  A series of Mannich base type derivatives of Glaucocalyxin A (GLA) were designed and prepared. The cytotoxicity of these compounds was evaluated against six tumor cell lines (SMMC-7721, B16, SGC-7901, A549, KB, HL-60). Most compounds exhibited potent antiproliferative effects with low micromolar IC50 values. Compound 1 with para methyl benzyl amine moiety and compound 16 with cyclohexylamine moiety displayed the highest inhibition efficacy. Significantly, the cytotoxicity of compound 1 was much lower than GLA against the normal human liver cell (HL-7702). The in vitro stability assay revealed that transformation of GLA to Mannich base type derivatives improved the compound stability in rat plasma. Finally, decomposition product analysis supported that compound 1 could act as a prodrug and release GLA in the intracellular environment.

  DOI：

  10.1016/j.ejmech.2014.08.061

文献信息

• Synthesis and biological evaluation of glaucocalyxin A derivatives as potential anticancer agents
  作者：Jing Yang、Yanli Liu、Chengwen Xue、Wei Yu、Jian Zhang、Chunhua Qiao

  DOI：10.1016/j.ejmech.2014.08.061

  日期：2014.10

  A series of Mannich base type derivatives of Glaucocalyxin A (GLA) were designed and prepared. The cytotoxicity of these compounds was evaluated against six tumor cell lines (SMMC-7721, B16, SGC-7901, A549, KB, HL-60). Most compounds exhibited potent antiproliferative effects with low micromolar IC50 values. Compound 1 with para methyl benzyl amine moiety and compound 16 with cyclohexylamine moiety displayed the highest inhibition efficacy. Significantly, the cytotoxicity of compound 1 was much lower than GLA against the normal human liver cell (HL-7702). The in vitro stability assay revealed that transformation of GLA to Mannich base type derivatives improved the compound stability in rat plasma. Finally, decomposition product analysis supported that compound 1 could act as a prodrug and release GLA in the intracellular environment.