6-bromo-N-(5-ethenyl-6,7-dimethoxynaphthalen-1-yl)-2,3-dimethoxy-N-methylbenzamide | 1415326-04-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 6-bromo-N-(5-ethenyl-6,7-dimethoxynaphthalen-1-yl)-2,3-dimethoxy-N-methylbenzamide
• CAS: 1415326-04-3
• 化学式: C₂₄H₂₄BrNO₅
• 分子量: 486.362
• InChiKey: HSIIPVRIWYDMKT-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.5
• 重原子数：
  31
• 可旋转键数：
  7
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.21
• 拓扑面积：
  57.2
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  6-bromo-N-(5-ethenyl-6,7-dimethoxynaphthalen-1-yl)-2,3-dimethoxy-N-methylbenzamide 在 lithium aluminium tetrahydride 、 palladium diacetate 、 三(邻甲基苯基)磷 、 silver carbonate 作用下， 以 四氢呋喃 、 N,N-二甲基甲酰胺 为溶剂， 生成 1-Ethenyl-2,3,7,8-tetramethoxy-5-methylbenzo[c]phenanthridin-5-ium;chloride
  参考文献：
  名称：

  Antibacterial activity of substituted 5-methylbenzo[c]phenanthridinium derivatives

  摘要：

  Antibiotic resistance has prompted efforts to discover antibiotics with novel mechanisms of action. FtsZ is an essential protein for bacterial cell division, and has been viewed as an attractive target for the development of new antibiotics. Sanguinarine is a benzophenanthridine alkaloid that prevents cytokinesis in bacteria by inhibiting FtsZ self-assembly. In this study, a series of 5-methylbenzo[c]phenanthridinium derivatives were synthesized and evaluated for antibacterial activity against Staphylococcus aureus and Enterococcus faecalis. The data indicate that the presence of a 1- or 12-phenyl substituent on 2,3,8,9-tetramethoxy-5-methylbenzo[c]phenanthridinium chloride significantly enhances antibacterial activity relative to the parent compound or sanguinarine. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2012.09.097
• 作为产物：
  描述：

  1-bromo-2,3-dimethoxy-5-nitronaphthalene 在 四(三苯基膦)钯 、 三丁基乙烯基锡 、 sodium hydride 、 三乙胺 、 tin(ll) chloride 作用下， 以 乙醇 、 二氯甲烷 、 水 、 N,N-二甲基甲酰胺 为溶剂， 生成 6-bromo-N-(5-ethenyl-6,7-dimethoxynaphthalen-1-yl)-2,3-dimethoxy-N-methylbenzamide
  参考文献：
  名称：

  Antibacterial activity of substituted 5-methylbenzo[c]phenanthridinium derivatives

  摘要：

  Antibiotic resistance has prompted efforts to discover antibiotics with novel mechanisms of action. FtsZ is an essential protein for bacterial cell division, and has been viewed as an attractive target for the development of new antibiotics. Sanguinarine is a benzophenanthridine alkaloid that prevents cytokinesis in bacteria by inhibiting FtsZ self-assembly. In this study, a series of 5-methylbenzo[c]phenanthridinium derivatives were synthesized and evaluated for antibacterial activity against Staphylococcus aureus and Enterococcus faecalis. The data indicate that the presence of a 1- or 12-phenyl substituent on 2,3,8,9-tetramethoxy-5-methylbenzo[c]phenanthridinium chloride significantly enhances antibacterial activity relative to the parent compound or sanguinarine. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2012.09.097

文献信息

• Antibacterial activity of substituted 5-methylbenzo[c]phenanthridinium derivatives
  作者：Ajit Parhi、Cody Kelley、Malvika Kaul、Daniel S. Pilch、Edmond J. LaVoie

  DOI：10.1016/j.bmcl.2012.09.097

  日期：2012.12

  Antibiotic resistance has prompted efforts to discover antibiotics with novel mechanisms of action. FtsZ is an essential protein for bacterial cell division, and has been viewed as an attractive target for the development of new antibiotics. Sanguinarine is a benzophenanthridine alkaloid that prevents cytokinesis in bacteria by inhibiting FtsZ self-assembly. In this study, a series of 5-methylbenzo[c]phenanthridinium derivatives were synthesized and evaluated for antibacterial activity against Staphylococcus aureus and Enterococcus faecalis. The data indicate that the presence of a 1- or 12-phenyl substituent on 2,3,8,9-tetramethoxy-5-methylbenzo[c]phenanthridinium chloride significantly enhances antibacterial activity relative to the parent compound or sanguinarine. (C) 2012 Elsevier Ltd. All rights reserved.