N-(6,7-methylenedioxyquinolin-4-yl)-N-butyl-2-bromo-5-nitrobenzamide | 538366-74-4

• 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: N-(6,7-methylenedioxyquinolin-4-yl)-N-butyl-2-bromo-5-nitrobenzamide
• 英文别名: 2-bromo-N-butyl-N-([1,3]dioxolo[4,5-g]quinolin-8-yl)-5-nitrobenzamide
• CAS: 538366-74-4
• 化学式: C₂₁H₁₈BrN₃O₅
• 分子量: 472.295
• InChiKey: JJTJVYUIBLPBMY-UHFFFAOYSA-N

物化性质

• 沸点：
  632.1±55.0 °C(Predicted)
• 密度：
  1.559±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.8
• 重原子数：
  30
• 可旋转键数：
  5
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.24
• 拓扑面积：
  97.5
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  N-(6,7-methylenedioxyquinolin-4-yl)-N-butyl-2-bromo-5-nitrobenzamide 在 palladium diacetate 、 Ra-Ni 、 一水合肼 、 三(邻甲基苯基)磷 、 silver carbonate 作用下， 以 乙醇 、 N,N-二甲基甲酰胺 为溶剂， 反应 5.0h， 生成 8-amino-5-butyl-2,3-methylenedioxy-5H-dibenzo[c,h][1,6]naphthyridin-6-one
  参考文献：
  名称：

  Nitro and Amino Substitution in the D-Ring of 5-(2-Dimethylaminoethyl)- 2,3-methylenedioxy-5H-dibenzo[c,h][1,6]naphthyridin-6-ones:  Effect on Topoisomerase-I Targeting Activity and Cytotoxicity

  摘要：

  5H-8,9-Dimethoxy-5-(2-N,N-dimethylaminoethyl)-2,3-methylenedioxydibenzo[c,h] [1,6]naphthyridin-6-one exhibits potent TOP1-targeting activity and pronounced antitumor activity. It was hypothesized that replacement of the two methoxyl groups with a nitro substituent would allow for retention of similar activity. In this study 8-, 9-, and 10-nitro-5H-2,3-methylenedioxy-5-(2-N,N-dimethylaminoethyl)dibenzo[c,h] [1,6]naphthyridin-6-one and their amino derivatives were synthesized and assessed for their relative TOP1-targeting activity and cytotoxicity. In the case of both the 8- and 9-nitro analogues, their TOP1-targeting activity and cytotoxicity are greater than that of camptothecin and comparable to that of 5H-8,9-dimethoxy-5-(2-N,N-dimethylaminoethyl)-2,3-methylenedioxydibenzo[c,h] [1,6]naphthyridin-6-one.

  DOI：

  10.1021/jm020498a
• 作为产物：
  描述：

  2-溴-5-硝基苯甲酸 在 草酰氯 、 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 75.0h， 生成 N-(6,7-methylenedioxyquinolin-4-yl)-N-butyl-2-bromo-5-nitrobenzamide
  参考文献：
  名称：

  Nitro and Amino Substitution in the D-Ring of 5-(2-Dimethylaminoethyl)- 2,3-methylenedioxy-5H-dibenzo[c,h][1,6]naphthyridin-6-ones:  Effect on Topoisomerase-I Targeting Activity and Cytotoxicity

  摘要：

  5H-8,9-Dimethoxy-5-(2-N,N-dimethylaminoethyl)-2,3-methylenedioxydibenzo[c,h] [1,6]naphthyridin-6-one exhibits potent TOP1-targeting activity and pronounced antitumor activity. It was hypothesized that replacement of the two methoxyl groups with a nitro substituent would allow for retention of similar activity. In this study 8-, 9-, and 10-nitro-5H-2,3-methylenedioxy-5-(2-N,N-dimethylaminoethyl)dibenzo[c,h] [1,6]naphthyridin-6-one and their amino derivatives were synthesized and assessed for their relative TOP1-targeting activity and cytotoxicity. In the case of both the 8- and 9-nitro analogues, their TOP1-targeting activity and cytotoxicity are greater than that of camptothecin and comparable to that of 5H-8,9-dimethoxy-5-(2-N,N-dimethylaminoethyl)-2,3-methylenedioxydibenzo[c,h] [1,6]naphthyridin-6-one.

  DOI：

  10.1021/jm020498a

文献信息

• Nitro and Amino Substitution in the D-Ring of 5-(2-Dimethylaminoethyl)- 2,3-methylenedioxy-5<i>H</i>-dibenzo[<i>c,h</i>][1,6]naphthyridin-6-ones:  Effect on Topoisomerase-I Targeting Activity and Cytotoxicity
  作者：Sudhir K. Singh、Alexander L. Ruchelman、Tsai-Kun Li、Angela Liu、Leroy F. Liu、Edmond J. LaVoie

  DOI：10.1021/jm020498a

  日期：2003.5.1

  5H-8,9-Dimethoxy-5-(2-N,N-dimethylaminoethyl)-2,3-methylenedioxydibenzo[c,h] [1,6]naphthyridin-6-one exhibits potent TOP1-targeting activity and pronounced antitumor activity. It was hypothesized that replacement of the two methoxyl groups with a nitro substituent would allow for retention of similar activity. In this study 8-, 9-, and 10-nitro-5H-2,3-methylenedioxy-5-(2-N,N-dimethylaminoethyl)dibenzo[c,h] [1,6]naphthyridin-6-one and their amino derivatives were synthesized and assessed for their relative TOP1-targeting activity and cytotoxicity. In the case of both the 8- and 9-nitro analogues, their TOP1-targeting activity and cytotoxicity are greater than that of camptothecin and comparable to that of 5H-8,9-dimethoxy-5-(2-N,N-dimethylaminoethyl)-2,3-methylenedioxydibenzo[c,h] [1,6]naphthyridin-6-one.