[(1R,4R,5R,7R,9R,10S,13R)-5-methoxycarbonyl-9-methyl-14-methylidene-15-oxo-7-tetracyclo[11.2.1.01,10.04,9]hexadecanyl] (4S,5R)-2,4-diphenyl-4,5-dihydro-1,3-oxazole-5-carboxylate | 926026-11-1

• 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: [(1R,4R,5R,7R,9R,10S,13R)-5-methoxycarbonyl-9-methyl-14-methylidene-15-oxo-7-tetracyclo[11.2.1.01,10.04,9]hexadecanyl] (4S,5R)-2,4-diphenyl-4,5-dihydro-1,3-oxazole-5-carboxylate
• CAS: 926026-11-1
• 化学式: C₃₆H₃₉NO₆
• 分子量: 581.709
• InChiKey: RHGOSCUSXLYSNV-OSXBPOEOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.6
• 重原子数：
  43
• 可旋转键数：
  7
• 环数：
  7.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  91.3
• 氢给体数：
  0
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  [(1R,4R,5R,7R,9R,10S,13R)-5-methoxycarbonyl-9-methyl-14-methylidene-15-oxo-7-tetracyclo[11.2.1.01,10.04,9]hexadecanyl] (4S,5R)-2,4-diphenyl-4,5-dihydro-1,3-oxazole-5-carboxylate 在 对甲苯磺酸 作用下， 以 二氯甲烷 为溶剂， 反应 96.0h， 以75%的产率得到methyl (1R,4R,5R,7R,9R,10S,13R)-7-[(2R,3S)-3-benzamido-2-hydroxy-3-phenylpropanoyl]oxy-9-methyl-14-methylidene-15-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 4-二甲氨基吡啶 、 manganese(IV) oxide 、 N,N'-二环己基碳二亚胺 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 3.3h， 生成 [(1R,4R,5R,7R,9R,10S,13R)-5-methoxycarbonyl-9-methyl-14-methylidene-15-oxo-7-tetracyclo[11.2.1.01,10.04,9]hexadecanyl] (4S,5R)-2,4-diphenyl-4,5-dihydro-1,3-oxazole-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

文献信息

• Cytotoxic Activity of Some Natural and Synthetic <i>ent</i>-Kauranes
  作者：Sergio Rosselli、Maurizio Bruno、Antonella Maggio、Gabriella Bellone、Tzu-Hsuan Chen、Kenneth F. Bastow、Kuo-Hsiung Lee

  DOI：10.1021/np060504w

  日期：2007.3.1

  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.