2,3-methylenedioxy-10,11-dimethoxy-13-methylprotoberberine iodide | 69776-36-9

• 分子结构分类: 有机化合物 - 生物碱及其衍生物 - 原小檗碱生物碱及其衍生物
• 英文名称: 2,3-methylenedioxy-10,11-dimethoxy-13-methylprotoberberine iodide
• 英文别名: 10,11-dimethoxy-13-methyl-5,6-dihydro-[1,3]dioxolo[4,5-g]isoquino[3,2-a]isoquinolinylium; iodide；5,6-Dihydro-10,11-dimethoxy-13-methylbenzo(g)-1,3-benzodioxolo(5,6-a)quinolizinium iodide；17,18-dimethoxy-21-methyl-5,7-dioxa-13-azoniapentacyclo[11.8.0.02,10.04,8.015,20]henicosa-1(21),2,4(8),9,13,15,17,19-octaene;iodide
• CAS: 69776-36-9
• 化学式: C₂₁H₂₀NO₄*I
• 分子量: 477.299
• InChiKey: NAAROFZUAGWEQH-UHFFFAOYSA-M

计算性质

• 辛醇/水分配系数(LogP)：
  0.41
• 重原子数：
  27
• 可旋转键数：
  2
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  40.8
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  10,11-dimethoxy-13c-methyl-(13ar)-5,8,13,13a-tetrahydro-6H-[1,3]dioxolo[4,5-g]isoquino[3,2-a]isoquinoline 生成 2,3-methylenedioxy-10,11-dimethoxy-13-methylprotoberberine iodide
  参考文献：
  名称：

  Conformations, DNA binding parameters, and antileukemic activity of certain cytotoxic protoberberine alkaloids

  摘要：

  The tetrahydroprotoberberine alkaloids 5 and 7 possessing a trans-quinolizidine conformation display in vitro KB cytotoxicities in contrast to their corresponding diastereomers 4 and 6 which exist in the cis-quinolizidine conformation and are much less toxic. The DNA-binding parameters of these compounds as well as the protoberberine salts 1, 8, and 9 have been examined by equilibrium dialysis. Only the quaternary salts bind to DNA. The alcohol 5 showed low in vivo activity against leukemia P388 systems, while the quaternary salts 8 and 9 proved to be toxic to the host.

  DOI：

  10.1021/jm00189a025

文献信息

• Conformations, DNA binding parameters, and antileukemic activity of certain cytotoxic protoberberine alkaloids
  作者：Mark Cushman、Frederick W. Dekow、Linda B. Jacobsen

  DOI：10.1021/jm00189a025

  日期：1979.3

  The tetrahydroprotoberberine alkaloids 5 and 7 possessing a trans-quinolizidine conformation display in vitro KB cytotoxicities in contrast to their corresponding diastereomers 4 and 6 which exist in the cis-quinolizidine conformation and are much less toxic. The DNA-binding parameters of these compounds as well as the protoberberine salts 1, 8, and 9 have been examined by equilibrium dialysis. Only the quaternary salts bind to DNA. The alcohol 5 showed low in vivo activity against leukemia P388 systems, while the quaternary salts 8 and 9 proved to be toxic to the host.