methyl 3-[2-[[(5S,5aS,8aR,9R)-8-oxo-9-(3,4,5-trimethoxyphenyl)-5a,6,8a,9-tetrahydro-5H-[2]benzofuro[5,6-f][1,3]benzodioxol-5-yl]amino]-2-oxoacetyl]-1H-indole-4-carboxylate | 1316852-84-2

• 分子结构分类: 有机化合物 - 木脂素、新木脂素和相关化合物 - 木脂素内酯
• 英文名称: methyl 3-[2-[[(5S,5aS,8aR,9R)-8-oxo-9-(3,4,5-trimethoxyphenyl)-5a,6,8a,9-tetrahydro-5H-[2]benzofuro[5,6-f][1,3]benzodioxol-5-yl]amino]-2-oxoacetyl]-1H-indole-4-carboxylate
• CAS: 1316852-84-2
• 化学式: C₃₄H₃₀N₂O₁₁
• 分子量: 642.619
• InChiKey: KTAFOMXHHHUMIF-AQFJBESNSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  47
• 可旋转键数：
  9
• 环数：
  7.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  161
• 氢给体数：
  2
• 氢受体数：
  11

反应信息

• 作为反应物：
  描述：

  methyl 3-[2-[[(5S,5aS,8aR,9R)-8-oxo-9-(3,4,5-trimethoxyphenyl)-5a,6,8a,9-tetrahydro-5H-[2]benzofuro[5,6-f][1,3]benzodioxol-5-yl]amino]-2-oxoacetyl]-1H-indole-4-carboxylate 、 乙酰氯 在 4-二甲氨基吡啶 、 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 6.0h， 以46%的产率得到methyl 3-[2-[[(5S,5aS,8aR,9R)-8-oxo-9-(3,4,5-trimethoxyphenyl)-5a,6,8a,9-tetrahydro-5H-[2]benzofuro[5,6-f][1,3]benzodioxol-5-yl]amino]-2-oxoacetyl]-1-acetylindole-4-carboxylate
  参考文献：
  名称：

  Synthesis and antitumor activity of novel podophyllotoxin derivatives against multidrug-resistant cancer cells

  摘要：

  Seven novel 4-N-substituted podophyllotoxin derivatives with indole rings were prepared and evaluated for cytotoxicity against human cancer cell lines HeLa, KB, KBV, K562, and K562/AO2. Most of them demonstrated improved antitumor activity and weak multidrug resistance compared to the drugs currently available.

  DOI：

  10.1080/10286020.2011.568941
• 作为产物：
  描述：

  吲哚-4-羧酸甲酯 在 4-二甲氨基吡啶 、 三乙胺 作用下， 以 乙醚 、 二氯甲烷 为溶剂， 反应 12.0h， 生成 methyl 3-[2-[[(5S,5aS,8aR,9R)-8-oxo-9-(3,4,5-trimethoxyphenyl)-5a,6,8a,9-tetrahydro-5H-[2]benzofuro[5,6-f][1,3]benzodioxol-5-yl]amino]-2-oxoacetyl]-1H-indole-4-carboxylate
  参考文献：
  名称：

  Synthesis and antitumor activity of novel podophyllotoxin derivatives against multidrug-resistant cancer cells

  摘要：

  Seven novel 4-N-substituted podophyllotoxin derivatives with indole rings were prepared and evaluated for cytotoxicity against human cancer cell lines HeLa, KB, KBV, K562, and K562/AO2. Most of them demonstrated improved antitumor activity and weak multidrug resistance compared to the drugs currently available.

  DOI：

  10.1080/10286020.2011.568941

文献信息

• Synthesis and antitumor activity of novel podophyllotoxin derivatives against multidrug-resistant cancer cells
  作者：Yong-En Guo、Hong Chen、Song Zuo、Dai-Lin Liu、Yan-Ling Lu、Jing-Jing Lv、Shao-Peng Wen、Tong-Cun Zhang

  DOI：10.1080/10286020.2011.568941

  日期：2011.5.1

  Seven novel 4-N-substituted podophyllotoxin derivatives with indole rings were prepared and evaluated for cytotoxicity against human cancer cell lines HeLa, KB, KBV, K562, and K562/AO2. Most of them demonstrated improved antitumor activity and weak multidrug resistance compared to the drugs currently available.