2,3,7,8-Tetramethoxy-5-methyl-1-phenylbenzo[c]phenanthridin-5-ium;chloride | 1235871-13-2

• 分子结构分类: 有机化合物 - 生物碱及其衍生物 - 苯并菲啶生物碱
• 英文名称: 2,3,7,8-Tetramethoxy-5-methyl-1-phenylbenzo[c]phenanthridin-5-ium;chloride
• CAS: 1235871-13-2
• 化学式: C₂₈H₂₆NO₄*Cl
• 分子量: 475.972
• InChiKey: UJCWVQUNEANYLM-UHFFFAOYSA-M

计算性质

• 辛醇/水分配系数(LogP)：
  2.68
• 重原子数：
  34
• 可旋转键数：
  5
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  40.8
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  1-bromo-2,3-dimethoxy-5-nitronaphthalene 在 lithium aluminium tetrahydride 、 四(三苯基膦)钯 、 palladium 10% on activated carbon 、 palladium diacetate 、 sodium hydride 、 sodium carbonate 、 一水合肼 、 三乙胺 、 三(邻甲基苯基)磷 、 silver carbonate 作用下， 以 四氢呋喃 、 乙醇 、 二氯甲烷 、 水 、 N,N-二甲基甲酰胺 、 甲苯 为溶剂， 生成 2,3,7,8-Tetramethoxy-5-methyl-1-phenylbenzo[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

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.