9-{[4-(Dimethylamino)benzyl]amino}-5-(3,4,5-trimethoxyphenyl)-5,5a,8a,9-tetrahydrofuro[3',4':6,7]naphtho[2,3-d][1,3]dioxol-6(8H)-one | 1341774-40-0

• 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: 9-{[4-(Dimethylamino)benzyl]amino}-5-(3,4,5-trimethoxyphenyl)-5,5a,8a,9-tetrahydrofuro[3',4':6,7]naphtho[2,3-d][1,3]dioxol-6(8H)-one
• 英文别名: (5S,5aS,8aR,9R)-5-[[4-(dimethylamino)phenyl]methylamino]-9-(3,4,5-trimethoxyphenyl)-5a,6,8a,9-tetrahydro-5H-[2]benzofuro[6,5-f][1,3]benzodioxol-8-one
• CAS: 1341774-40-0
• 化学式: C₃₁H₃₄N₂O₇
• 分子量: 546.62
• InChiKey: CAGAGRLEQWBGFC-ALMBTRMVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.9
• 重原子数：
  40
• 可旋转键数：
  8
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.39
• 拓扑面积：
  87.7
• 氢给体数：
  1
• 氢受体数：
  9

反应信息

• 作为产物：
  描述：

  4β-azido-4-deoxypodophyllotoxin 在 sodium tetrahydroborate 、 palladium 10% on activated carbon 、 碳酸氢铵 、 溶剂黄146 作用下， 以 甲醇 、 乙醇 、 4-(dicyanomethylene)-2-methyl-6-(p-dimethylaminostyryl)-4H-pyran 为溶剂， 反应 19.0h， 生成 9-{[4-(Dimethylamino)benzyl]amino}-5-(3,4,5-trimethoxyphenyl)-5,5a,8a,9-tetrahydrofuro[3',4':6,7]naphtho[2,3-d][1,3]dioxol-6(8H)-one
  参考文献：
  名称：

  Design, synthesis, and antitumor activity of novel podophyllotoxin derivatives as potent anticancer agents

  摘要：

  In order to find novel synthetic compounds with superior antitumor activity and overcome multidrug resistance, a series of novel 4-N-substituted podophyllotoxin derivatives were synthesized under mild conditions with satisfactory yield. Nine novel podophyllotoxin derivatives were synthesized by linking 4-amino-podophyllotoxin with aldehydes via the formation of a Schiff's base, and imines were reducted to secondary amines. These novel derivatives have been evaluated for cytotoxicity against human cancer cell lines Hela, K562, and K562/AO2. The results indicated that these compounds possess superior bioactivity (IC50 values were found at the range of 10(-6)-10(-8)mol/l) and weak multidrug resistance.

  DOI：

  10.1080/10286020.2013.802688

文献信息

• Design, synthesis, and antitumor activity of novel podophyllotoxin derivatives as potent anticancer agents
  作者：Jing Liu、Bo Cao、Ying Gao、Mei Bai、Xin Mei、Hong Chen、Yun-Gen Jiang、Da-Jiang Huang

  DOI：10.1080/10286020.2013.802688

  日期：2013.9

  In order to find novel synthetic compounds with superior antitumor activity and overcome multidrug resistance, a series of novel 4-N-substituted podophyllotoxin derivatives were synthesized under mild conditions with satisfactory yield. Nine novel podophyllotoxin derivatives were synthesized by linking 4-amino-podophyllotoxin with aldehydes via the formation of a Schiff's base, and imines were reducted to secondary amines. These novel derivatives have been evaluated for cytotoxicity against human cancer cell lines Hela, K562, and K562/AO2. The results indicated that these compounds possess superior bioactivity (IC50 values were found at the range of 10(-6)-10(-8)mol/l) and weak multidrug resistance.