2,4,7,8-tetrabromo-1-hydroxyphenazine

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二氮杂萘
• 英文名称: 2,4,7,8-tetrabromo-1-hydroxyphenazine
• 英文别名: 2,4,7,8-Tetrabromophenazin-1-ol；2,4,7,8-tetrabromophenazin-1-ol
• 化学式: C₁₂H₄Br₄N₂O
• 分子量: 511.793
• InChiKey: AFNWOKAEOJCYNR-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5
• 重原子数：
  19
• 可旋转键数：
  0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  46
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  3-甲氧基儿茶酚 在 N-溴代丁二酰亚胺(NBS) 、 邻四氯苯醌 、 三溴化硼 作用下， 以 乙醚 、 二氯甲烷 、 溶剂黄146 、 甲苯 为溶剂， 反应 30.0h， 生成 2,4,7,8-tetrabromo-1-hydroxyphenazine
  参考文献：
  名称：

  结构-活性关系的针对持久，耐抗生素的细菌生物膜和结核分枝杆菌的不同种类的卤代吩嗪。

  摘要：

  持久性细菌，包括表面附着的生物膜中的持久性细胞和生长缓慢的病原体，会导致对抗生素具有耐受性的慢性感染。在这里，我们描述了由2-溴-1- hydroxyphenazine启发一系列卤化吩嗪（HP）的结构-活性关系1。我们使用多种合成途径，探查了HP支架在2、4、7和8位的各种取代，提供了有关其抗菌和细菌根除特性的重要信息。卤代吩嗪14被证明是针对MRSA（MBEC <10μM），MRSE（MBEC = 2.35μM）和VRE（MBEC = 0.20μM）生物膜的最有效的生物膜根除剂（≥99.9％持久性细胞杀伤），而11和11 12证明对结核分枝杆菌具有出色的抗菌活性（MIC = 3.13μM）。与抗菌肽模拟物通过一般的膜裂解作用来消灭生物膜不同，HP不会裂解红细胞。HP是有前途的试剂，可以有效地靶向持久性细菌，同时证明对哺乳动物细胞的毒性可忽略不计。

  DOI：

  10.1021/acs.jmedchem.5b02004

文献信息

• Halogenated Phenazines that Potently Eradicate Biofilms, MRSA Persister Cells in Non‐Biofilm Cultures, and <i>Mycobacterium tuberculosis</i>
  作者：Aaron T. Garrison、Yasmeen Abouelhassan、Dimitris Kallifidas、Fang Bai、Maria Ukhanova、Volker Mai、Shouguang Jin、Hendrik Luesch、Robert W. Huigens

  DOI：10.1002/anie.201508155

  日期：2015.12

  against non‐replicating bacteria (for example, bacteria within biofilms). We report a series of halogenated phenazines (HP), inspired by marine antibiotic 1, that targets persistent bacteria. HP 14 demonstrated the most potent biofilm eradication activities to date against MRSA, MRSE, and VRE biofilms (MBEC=0.2–12.5 μM), as well as the effective killing of MRSA persister cells in non‐biofilm cultures

  常规抗生素对非复制性细菌（例如生物膜内的细菌）无效。我们报告了一系列受海洋抗生素1启发的卤化吩嗪（HP），其针对持久性细菌。HP 14展示了迄今为止针对MRSA，MRSE和VRE生物膜（MBEC = 0.2–12.5μM）的最有效的生物膜根除活动，以及在非生物膜培养物中可有效杀死MRSA持久性细胞。一线治疗MRSA，万古霉素和达托霉素，无法根除MRSA生物膜或非生物膜，持久旁边14。HP 13显示强抗菌活性对生长缓慢的分枝 杆菌（MIC = 3.13μM），这是全球细菌感染致死的主要原因。HP类似物通过对哺乳动物细胞无毒的机制有效靶向持久性细菌，并且可能对慢性细菌感染的治疗产生重大影响。
• PHENAZINE DERIVATIVES AS ANTIMICROBIAL AGENTS
  申请人：Huigens, III Robert William

  公开号：US20180312473A1

  公开（公告）日：2018-11-01

  The present invention provides novel phenazine derivatives, such as compounds of Formula (I′) (e.g., Formula (I)), (II), and (III), and pharmaceutically acceptable salts thereof. The compounds of the invention are expected to be antimicrobial agents and may act by a microbial warfare strategy (e.g., a reactive oxygen species (ROS)-based competition strategy). The present invention also provides pharmaceutical compositions, kits, uses, and methods that involve the compounds of the invention and may be useful in preventing or treating a microbial infection (e.g., a bacterial infection or mycobacterial infection) in a subject, inhibiting the mycobacterium ), inhibiting the formation and/or growth of a biofilm, reducing or clearing a biofilm, and/or disinfecting a surface.
• [EN] PHENAZINE DERIVATIVES AS ANTIMICROBIAL AGENTS<br/>[FR] DÉRIVÉS DE PHÉNAZINE UTILISÉS COMME AGENTS ANTIMICROBIENS
  申请人：UNIV FLORIDA

  公开号：WO2017011730A2

  公开（公告）日：2017-01-19

  The present invention provides novel phenazine derivatives, such as compounds of Formula (I') (e.g., Formula (I)), (II), and (III), and pharmaceutically acceptable salts thereof. The compounds of the invention are expected to be antimicrobial agents and may act by a microbial warfare strategy (e.g., a reactive oxygen species (ROS)-based competition strategy). The present invention also provides pharmaceutical compositions, kits, uses, and methods that involve the compounds of the invention and may be useful in preventing or treating a microbial infection (e.g., a bacterial infection or mycobacterial infection) in a subject, inhibiting the growth and/or reproduction of a microorganism (e.g., a bacterium or mycobacterium), killing a microorganism (e.g., a bacterium or mycobacterium), inhibiting the formation and/or growth of a biofilm, reducing or clearing a biofilm, and/or disinfecting a surface.