methyl (1'R,4'R,5'R,9'R,10'S,13'R)-9'-methyl-14'-methylidene-15'-oxospiro[1,3-dioxolane-2,7'-tetracyclo[11.2.1.01,10.04,9]hexadecane]-5'-carboxylate | 926026-13-3

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: methyl (1'R,4'R,5'R,9'R,10'S,13'R)-9'-methyl-14'-methylidene-15'-oxospiro[1,3-dioxolane-2,7'-tetracyclo[11.2.1.01,10.04,9]hexadecane]-5'-carboxylate
• CAS: 926026-13-3
• 化学式: C₂₂H₃₀O₅
• 分子量: 374.477
• InChiKey: MXARVTFIZJOZGD-RYQGBKPXSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  27
• 可旋转键数：
  2
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.82
• 拓扑面积：
  61.8
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  methyl (1'R,4'R,5'R,9'R,10'S,13'R)-9'-methyl-14'-methylidene-15'-oxospiro[1,3-dioxolane-2,7'-tetracyclo[11.2.1.01,10.04,9]hexadecane]-5'-carboxylate 在 sodium tetrahydroborate 、 对甲苯磺酸 作用下， 以 甲醇 、 水 为溶剂， 反应 2.17h， 生成 methyl (1R,4R,5R,9R,10S,13R,15R)-15-hydroxy-9-methyl-14-methylidene-7-oxotetracyclo[11.2.1.01,10.04,9]hexadecane-5-carboxylate
  参考文献：
  名称：

  Cytotoxic Activity of Some Natural and Synthetic ent-Kauranes

  摘要：

  Atractyligenin (1) and several synthetic derivatives were tested and found to be active against tumor cell replication. Compound 1 was readily converted to the 2,15-diketo (3) or 15-keto (4) derivatives, which contain an alpha,beta-unsaturated ketone. Compounds 3 and 4 showed significant cytotoxic activity against all six tested cancer cell lines and were most potent against 1A9 ovarian cancer cells with EC50 values of 0.2 and 0.3 mu M, respectively. These two 1-analogues are promising lead compounds for further investigation.

  DOI：

  10.1021/np060504w
• 作为产物：
  描述：

  atractyligenin 在 manganese(IV) oxide 、 对甲苯磺酸 作用下， 以 四氢呋喃 、 苯 为溶剂， 反应 5.25h， 生成 methyl (1'R,4'R,5'R,9'R,10'S,13'R)-9'-methyl-14'-methylidene-15'-oxospiro[1,3-dioxolane-2,7'-tetracyclo[11.2.1.01,10.04,9]hexadecane]-5'-carboxylate
  参考文献：
  名称：

  Cytotoxic Activity of Some Natural and Synthetic ent-Kauranes

  摘要：

  Atractyligenin (1) and several synthetic derivatives were tested and found to be active against tumor cell replication. Compound 1 was readily converted to the 2,15-diketo (3) or 15-keto (4) derivatives, which contain an alpha,beta-unsaturated ketone. Compounds 3 and 4 showed significant cytotoxic activity against all six tested cancer cell lines and were most potent against 1A9 ovarian cancer cells with EC50 values of 0.2 and 0.3 mu M, respectively. These two 1-analogues are promising lead compounds for further investigation.

  DOI：

  10.1021/np060504w