ent-1α-O-acetyl-14β-O-(o-chlorobenzoyl)-6,7,15-trioxo-7,20-epoxy-6,7-seco-16-kaurene | 1422272-59-0

• 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: ent-1α-O-acetyl-14β-O-(o-chlorobenzoyl)-6,7,15-trioxo-7,20-epoxy-6,7-seco-16-kaurene
• 英文别名: [(1R,2'R,4'S,5S,6S,9S,12R)-4'-acetyloxy-2'-formyl-1',1'-dimethyl-10-methylidene-2,11-dioxospiro[3-oxatricyclo[7.2.1.01,6]dodecane-5,3'-cyclohexane]-12-yl] 2-chlorobenzoate
• CAS: 1422272-59-0
• 化学式: C₂₉H₃₁ClO₈
• 分子量: 543.013
• InChiKey: YCVRUWLDSAOQJW-VSJALRRTSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.5
• 重原子数：
  38
• 可旋转键数：
  6
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.55
• 拓扑面积：
  113
• 氢给体数：
  0
• 氢受体数：
  8

反应信息

• 作为产物：
  描述：

  冬凌草素 在 4-二甲氨基吡啶 、 lead(IV) tetraacetate 、 sodium carbonate 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 生成 ent-1α-O-acetyl-14β-O-(o-chlorobenzoyl)-6,7,15-trioxo-7,20-epoxy-6,7-seco-16-kaurene
  参考文献：
  名称：

  Synthesis of spirolactone-type diterpenoid derivatives from kaurene-type oridonin with improved antiproliferative effects and their apoptosis-inducing activity in human hepatoma Bel-7402 cells

  摘要：

  A series of novel spirolactone-type diterpenoid derivatives of oridonin (12a-j) were designed and synthesized. All the target compounds showed improved anti-proliferative activity against a panel of human cancer cell lines and the most effective compound 12j was more potent than positive control Taxol in 1062 and Bel-7402 cells with IC50 values of 0.39 mu M and 1.39 mu M, respectively. The cellular mechanisms showed that compound 12j induced apoptosis at low micromolar concentrations in human hepatoma Bel-7402 cells. These results demonstrate that the spirolactone-type diterpenoid derivatives of oridonin have optimized growth inhibitory activity against cancer cells and interesting apoptosis-inducing ability. (C) 2012 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2012.11.002