6-bromo-N-(5-cyclopropyl-6,7-dimethoxynaphthalen-1-yl)-2,3-dimethoxybenzamide | 1235871-65-4

• 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-cyclopropyl-6,7-dimethoxynaphthalen-1-yl)-2,3-dimethoxybenzamide
• CAS: 1235871-65-4
• 化学式: C₂₄H₂₄BrNO₅
• 分子量: 486.362
• InChiKey: MRDWQMLXRACIEC-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：
  4.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  66
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  6-bromo-N-(5-cyclopropyl-6,7-dimethoxynaphthalen-1-yl)-2,3-dimethoxybenzamide 在 lithium aluminium tetrahydride 、 palladium diacetate 、 sodium hydride 、 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-Cyclopropyl-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：

  2,3-二甲氧基-6-溴苯甲酸 在 草酰氯 、 三乙胺 作用下， 以 二氯甲烷 为溶剂， 生成 6-bromo-N-(5-cyclopropyl-6,7-dimethoxynaphthalen-1-yl)-2,3-dimethoxybenzamide
  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

• [EN] BENZO [C] PHENANTHRIDINES AS ANTIMICROBIAL AGENTS<br/>[FR] BENZO[C]PHÉNANTHRIDINES COMME AGENTS ANTIMICROBIENS
  申请人：UNIV RUTGERS

  公开号：WO2010083436A1

  公开（公告）日：2010-07-22

  The present invention provides compounds of formula I: formula (I) wherein X1- X4 and R1-R12 have any of the values defined in the specification, as well as salts and prodrugs thereof, which inhibit major molecular mechanisms associated with bacterial cell division and proliferation so as to be useful for the treatment and/or prevention of bacterial infections. The invention also provides compositions comprising these compounds as well as methods for using these compounds to inhibit bacterial cell division and proliferation and to treat bacterial infections.

  本发明提供了以下式I的化合物：式(I)其中X1-X4和R1-R12具有规范中定义的任何值，以及其盐和前药，这些化合物抑制与细菌细胞分裂和增殖相关的主要分子机制，因此可用于治疗和/或预防细菌感染。该发明还提供了包含这些化合物的组合物，以及使用这些化合物抑制细菌细胞分裂和增殖并治疗细菌感染的方法。
• BENZO [C] PHENANTHRIDINES AS ANTIMICROBIAL AGENTS
  申请人：LaVoie Edmond J.

  公开号：US20120022061A1

  公开（公告）日：2012-01-26

  The present invention provides compounds of formula I: formula (I) wherein X 1 -X 4 and R 1 -R 12 have any of the values defined in the specification, as well as salts and prodrugs thereof, which inhibit major molecular mechanisms associated with bacterial cell division and proliferation so as to be useful for the treatment and/or prevention of bacterial infections. The invention also provides compositions comprising these compounds as well as methods for using these compounds to inhibit bacterial cell division and proliferation and to treat bacterial infections.

  本发明提供了式I的化合物：式（I）其中X1-X4和R1-R12具有规范中定义的任何值，以及其盐和前药，可以抑制与细菌细胞分裂和增殖相关的主要分子机制，因此可用于治疗和/或预防细菌感染。本发明还提供了包含这些化合物的组合物，以及使用这些化合物抑制细菌细胞分裂和增殖并治疗细菌感染的方法。
• US8741917B2
  申请人：——

  公开号：US8741917B2

  公开（公告）日：2014-06-03