5-bromo-N-(6,7-dimethoxynaphthalen-1-yl)benzo[d][1,3]dioxole-4-carboxamide

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 5-bromo-N-(6,7-dimethoxynaphthalen-1-yl)benzo[d][1,3]dioxole-4-carboxamide
• 英文别名: 5-bromo-N-(6,7-dimethoxynaphthalen-1-yl)-1,3-benzodioxole-4-carboxamide
• 化学式: C₂₀H₁₆BrNO₅
• 分子量: 430.255
• InChiKey: YVIXHRDWNXXZMM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.5
• 重原子数：
  27
• 可旋转键数：
  4
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.15
• 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：

  5-bromo-N-(6,7-dimethoxynaphthalen-1-yl)benzo[d][1,3]dioxole-4-carboxamide 在 palladium diacetate 、 sodium hydride 、 三(邻甲基苯基)磷 、 silver carbonate 作用下， 以 N,N-二甲基甲酰胺 、 mineral oil 为溶剂， 反应 4.0h， 生成 12-(2-(dimethylamino)ethyl)-9,10-dimethoxybenzo[c][1,3]dioxolo[4,5-i]phenanthridin-13(12H)-one
  参考文献：
  名称：

  Synthesis of Methoxy-, Methylenedioxy-, Hydroxy-, and Halo-Substituted Benzophenanthridinone Derivatives as DNA Topoisomerase IB (TOP1) and Tyrosyl-DNA Phosphodiesterase 1 (TDP1) Inhibitors and Their Biological Activity for Drug-Resistant Cancer

  摘要：

  DOI：

  10.1021/acs.jmedchem.1c00318
• 作为产物：
  描述：

  5-溴-1,3-苯并间二氧杂环戊烯-4-羧酸 在 氯化亚砜 、 三甲胺 作用下， 以 二氯甲烷 为溶剂， 反应 14.0h， 生成 5-bromo-N-(6,7-dimethoxynaphthalen-1-yl)benzo[d][1,3]dioxole-4-carboxamide
  参考文献：
  名称：

  Synthesis of Methoxy-, Methylenedioxy-, Hydroxy-, and Halo-Substituted Benzophenanthridinone Derivatives as DNA Topoisomerase IB (TOP1) and Tyrosyl-DNA Phosphodiesterase 1 (TDP1) Inhibitors and Their Biological Activity for Drug-Resistant Cancer

  摘要：

  DOI：

  10.1021/acs.jmedchem.1c00318

文献信息

• 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。
• 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.
• US8741917B2
  申请人：——

  公开号：US8741917B2

  公开（公告）日：2014-06-03
• Synthesis of Methoxy-, Methylenedioxy-, Hydroxy-, and Halo-Substituted Benzophenanthridinone Derivatives as DNA Topoisomerase IB (TOP1) and Tyrosyl-DNA Phosphodiesterase 1 (TDP1) Inhibitors and Their Biological Activity for Drug-Resistant Cancer
  作者：De-Xuan Hu、Wen-Lin Tang、Yu Zhang、Hao Yang、Wenjie Wang、Keli Agama、Yves Pommier、Lin-Kun An

  DOI：10.1021/acs.jmedchem.1c00318

  日期：2021.6.10