1-Benzyloxy-2-methoxy-12-methyl-13-phenyl-12,13-dihydro-[1,3]dioxolo[4',5':4,5]benzo[1,2-c]phenanthridine | 209157-93-7

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 1-Benzyloxy-2-methoxy-12-methyl-13-phenyl-12,13-dihydro-[1,3]dioxolo[4',5':4,5]benzo[1,2-c]phenanthridine
• 英文别名: 2-methoxy-12-methyl-13-phenyl-1-phenylmethoxy-13H-[1,3]benzodioxolo[5,6-c]phenanthridine
• CAS: 209157-93-7
• 化学式: C₃₃H₂₇NO₄
• 分子量: 501.582
• InChiKey: FNFNUSZIVGPXCT-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.4
• 重原子数：
  38
• 可旋转键数：
  5
• 环数：
  7.0
• sp3杂化的碳原子比例：
  0.15
• 拓扑面积：
  40.2
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  1-Benzyloxy-2-methoxy-12-methyl-13-phenyl-12,13-dihydro-[1,3]dioxolo[4',5':4,5]benzo[1,2-c]phenanthridine 在 盐酸 、 溶剂黄146 、 2,3-二氯-5,6-二氰基-1,4-苯醌 作用下， 以 二氯甲烷 为溶剂， 生成 1-Hydroxy-2-methoxy-12-methyl-13-phenyl-[1,3]dioxolo[4',5':4,5]benzo[1,2-c]phenanthridin-12-ium; 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：

  phenylmagnesium bromide 、 2,3-(methylenedioxy)-5-methyl-6-ethoxy-7-benzyloxy-8-methoxy-5,6-dihydrobenzo[c]phenanthridine 以 四氢呋喃 为溶剂， 生成 1-Benzyloxy-2-methoxy-12-methyl-13-phenyl-12,13-dihydro-[1,3]dioxolo[4',5':4,5]benzo[1,2-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