2-Methoxy-13-methyl-1-phenylmethoxy-[1,3]benzodioxolo[5,6-c]phenanthridine | 209157-84-6

• 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: 2-Methoxy-13-methyl-1-phenylmethoxy-[1,3]benzodioxolo[5,6-c]phenanthridine
• 英文别名: 2-methoxy-13-methyl-1-phenylmethoxy-[1,3]benzodioxolo[5,6-c]phenanthridine
• CAS: 209157-84-6
• 化学式: C₂₇H₂₁NO₄
• 分子量: 423.468
• InChiKey: IHFOKBDWQIOEPB-UHFFFAOYSA-N

物化性质

• 沸点：
  633.328±50.00 °C(Press: 760.00 Torr)(predicted)
• 密度：
  1.319±0.06 g/cm3(Temp: 25 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  6.3
• 重原子数：
  32
• 可旋转键数：
  4
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.15
• 拓扑面积：
  49.8
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  三氟甲烷磺酸甲酯 、 2-Methoxy-13-methyl-1-phenylmethoxy-[1,3]benzodioxolo[5,6-c]phenanthridine 在 盐酸 、 溶剂黄146 作用下， 以 甲苯 为溶剂， 以91%的产率得到2-Methoxy-12,13-dimethyl-[1,3]benzodioxolo[5,6-c]phenanthridin-12-ium-1-ol;chloride
  参考文献：
  名称：

  Synthesis of derivatives of NK109, 7-OH Benzo[c]phenanthridine alkaloid, and evaluation of their cytotoxicities and reduction-resistant properties

  摘要：

  The N-5-C-6 double bond of NK109 (an antitumor benzo[c]phenanthridine alkaloid) is easily reduced under biological environment. To suppress the inactivation caused by reduction, we synthesized 5-, 6-, and 8-substituted NK109. 5-Substituted derivatives (4a-c) were reduced more easily than NK109. 6-Substituted ones (10a-f) inhibited biological reduction, but showed weak cytotoxic activity. 8-O-Substituted ones (13a-h), especially 8-O-hydroxyethyl NK109 (13d), suppressed biological reduction and exhibited strong cytotoxic activity. (C) 2000 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(00)00467-4
• 作为产物：
  描述：

  2-methoxy-12,13-dimethyl-1-phenylmethoxy-13H-[1,3]benzodioxolo[5,6-c]phenanthridine 在 manganese(IV) oxide 作用下， 以 甲苯 为溶剂， 生成 2-Methoxy-13-methyl-1-phenylmethoxy-[1,3]benzodioxolo[5,6-c]phenanthridine
  参考文献：
  名称：

  Synthesis of derivatives of NK109, 7-OH Benzo[c]phenanthridine alkaloid, and evaluation of their cytotoxicities and reduction-resistant properties

  摘要：

  The N-5-C-6 double bond of NK109 (an antitumor benzo[c]phenanthridine alkaloid) is easily reduced under biological environment. To suppress the inactivation caused by reduction, we synthesized 5-, 6-, and 8-substituted NK109. 5-Substituted derivatives (4a-c) were reduced more easily than NK109. 6-Substituted ones (10a-f) inhibited biological reduction, but showed weak cytotoxic activity. 8-O-Substituted ones (13a-h), especially 8-O-hydroxyethyl NK109 (13d), suppressed biological reduction and exhibited strong cytotoxic activity. (C) 2000 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(00)00467-4

文献信息

• Synthesis of derivatives of NK109, 7-OH Benzo[c]phenanthridine alkaloid, and evaluation of their cytotoxicities and reduction-resistant properties
  作者：Takeshi Nakanishi、Akira Masuda、Masato Suwa、Yuji Akiyama、Naoko Hoshino-Abe、Masanobu Suzuki

  DOI：10.1016/s0960-894x(00)00467-4

  日期：2000.10

  The N-5-C-6 double bond of NK109 (an antitumor benzo[c]phenanthridine alkaloid) is easily reduced under biological environment. To suppress the inactivation caused by reduction, we synthesized 5-, 6-, and 8-substituted NK109. 5-Substituted derivatives (4a-c) were reduced more easily than NK109. 6-Substituted ones (10a-f) inhibited biological reduction, but showed weak cytotoxic activity. 8-O-Substituted ones (13a-h), especially 8-O-hydroxyethyl NK109 (13d), suppressed biological reduction and exhibited strong cytotoxic activity. (C) 2000 Elsevier Science Ltd. All rights reserved.