8-O-desmethyl-N-nornitidine

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 喹啉及其衍生物
• 英文名称: 8-O-desmethyl-N-nornitidine
• 英文别名: 9-hydroxy-8-methoxy-2,3-methylenedioxybenzo[c]phenanthridine；norisoterihanine；2-Methoxy-[1,3]benzodioxolo[5,6-c]phenanthridin-3-ol；2-methoxy-[1,3]benzodioxolo[5,6-c]phenanthridin-3-ol
• 化学式: C₁₉H₁₃NO₄
• 分子量: 319.317
• InChiKey: ZCMNYBNYFRAPIS-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.1
• 重原子数：
  24
• 可旋转键数：
  1
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.11
• 拓扑面积：
  60.8
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  8-O-desmethyl-N-nornitidine 在 Jones reagent 作用下， 以 丙酮 为溶剂， 反应 13.0h， 生成 isoterihanine chloride
  参考文献：
  名称：

  Total Synthesis of the Benzo[c]phenanthridine Alkaloids, Terihanine and Isoterihanine, and Their Antitumor Activity

  摘要：

  A new total synthesis of terihanine (2a) and isoterihanine (2b) was established by our new bond formation between the C4b and N5 positions of the benzo[c]phenanthridine ring based on a microwave-assisted thermal electrocyclic reaction of 2-cycloalkenylbenzaldoxime as an aza 6 pi-electron system. In addition, the antitumor activity of these synthesized compounds, including nitidine and nornitidine was evaluated in HCT-116 cells.

  DOI：

  10.3987/com-13-s(s)16
• 作为产物：
  描述：

  2-(6,7-methylenedioxy-3,4-diydronaphthyl)boronic acid pinacol ester 在 bis-triphenylphosphine-palladium(II) chloride 、 palladium 10% on activated carbon 、 sodium acetate 、 potassium carbonate 作用下， 以 甲醇 、 乙醇 、 N,N-二甲基甲酰胺 、 邻二氯苯 为溶剂， 反应 16.0h， 生成 8-O-desmethyl-N-nornitidine
  参考文献：
  名称：

  Total Synthesis of the Benzo[c]phenanthridine Alkaloids, Terihanine and Isoterihanine, and Their Antitumor Activity

  摘要：

  A new total synthesis of terihanine (2a) and isoterihanine (2b) was established by our new bond formation between the C4b and N5 positions of the benzo[c]phenanthridine ring based on a microwave-assisted thermal electrocyclic reaction of 2-cycloalkenylbenzaldoxime as an aza 6 pi-electron system. In addition, the antitumor activity of these synthesized compounds, including nitidine and nornitidine was evaluated in HCT-116 cells.

  DOI：

  10.3987/com-13-s(s)16