5-bromo-N,N'-diethoxycarbonyltetrandrine | 1400913-99-6

• 分子结构分类: 有机化合物 - 木脂素、新木脂素和相关化合物
• 英文名称: 5-bromo-N,N'-diethoxycarbonyltetrandrine
• 英文别名: diethyl (1S,14S)-19-bromo-9,20,21,25-tetramethoxy-7,23-dioxa-15,30-diazaheptacyclo[22.6.2.23,6.18,12.114,18.027,31.022,33]hexatriaconta-3(36),4,6(35),8,10,12(34),18(33),19,21,24,26,31-dodecaene-15,30-dicarboxylate
• CAS: 1400913-99-6
• 化学式: C₄₂H₄₅BrN₂O₁₀
• 分子量: 817.731
• InChiKey: KLUHQZLMVZZNBZ-CONSDPRKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.8
• 重原子数：
  55
• 可旋转键数：
  8
• 环数：
  8.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  115
• 氢给体数：
  0
• 氢受体数：
  10

反应信息

• 作为反应物：
  描述：

  5-bromo-N,N'-diethoxycarbonyltetrandrine 在 potassium hydroxide 作用下， 以 甲醇 为溶剂， 反应 72.0h， 以45%的产率得到5-bromo-N,N'-didemethyltetrandrine
  参考文献：
  名称：

  Partial synthesis and biological evaluation of bisbenzylisoquinoline alkaloids derivatives: potential modulators of multidrug resistance in cancer

  摘要：

  A series of new bisbenzylisoquinoline alkaloids was partially synthesized from tetrandrine and fangchinoline and evaluated for their ability to reverse P-glycoprotein-mediated multidrug resistance (MDR) in cancer cells. All the test compounds increased the intracellular accumulation rate of rhodamine 123 in MDR cells (Bel7402 and HCT8), and most exhibited more potent MDR-reversing activity relative to the reference compound verapamil. Compounds 8, 10, 13, and 14 enhanced intracellular accumulation of doxorubicin in Bel7402 and HCT8 cells.

  DOI：

  10.1080/10286020.2012.680443
• 作为产物：
  描述：

  溴泰君 、 氯甲酸乙酯 在 sodium carbonate 作用下， 以 二氯甲烷 为溶剂， 反应 4.0h， 以69%的产率得到5-bromo-N,N'-diethoxycarbonyltetrandrine
  参考文献：
  名称：

  Partial synthesis and biological evaluation of bisbenzylisoquinoline alkaloids derivatives: potential modulators of multidrug resistance in cancer

  摘要：

  A series of new bisbenzylisoquinoline alkaloids was partially synthesized from tetrandrine and fangchinoline and evaluated for their ability to reverse P-glycoprotein-mediated multidrug resistance (MDR) in cancer cells. All the test compounds increased the intracellular accumulation rate of rhodamine 123 in MDR cells (Bel7402 and HCT8), and most exhibited more potent MDR-reversing activity relative to the reference compound verapamil. Compounds 8, 10, 13, and 14 enhanced intracellular accumulation of doxorubicin in Bel7402 and HCT8 cells.

  DOI：

  10.1080/10286020.2012.680443

文献信息

• Partial synthesis and biological evaluation of bisbenzylisoquinoline alkaloids derivatives: potential modulators of multidrug resistance in cancer
  作者：Ping He、Hua Sun、Xi-Xian Jian、Qiao-Hong Chen、Dong-Lin Chen、Geng-Tao Liu、Feng-Peng Wang

  DOI：10.1080/10286020.2012.680443

  日期：2012.6

  A series of new bisbenzylisoquinoline alkaloids was partially synthesized from tetrandrine and fangchinoline and evaluated for their ability to reverse P-glycoprotein-mediated multidrug resistance (MDR) in cancer cells. All the test compounds increased the intracellular accumulation rate of rhodamine 123 in MDR cells (Bel7402 and HCT8), and most exhibited more potent MDR-reversing activity relative to the reference compound verapamil. Compounds 8, 10, 13, and 14 enhanced intracellular accumulation of doxorubicin in Bel7402 and HCT8 cells.