9-ethylphenazin-1-ol | 21050-66-8

• 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: 9-ethylphenazin-1-ol
• 英文别名: 1-Hydroxy-8-ethyl-phenazin；9-Aethyl-phenazin-1-ol
• CAS: 21050-66-8
• 化学式: C₁₄H₁₂N₂O
• 分子量: 224.262
• InChiKey: DEUUSKRYHLDYFC-UHFFFAOYSA-N

物化性质

• 沸点：
  442.5±15.0 °C(predicted)
• 密度：
  1.278±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  17
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.14
• 拓扑面积：
  46
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  9-ethylphenazin-1-ol 、 硫酸二甲酯 生成 1-ethyl-9-hydroxy-5-methyl-phenazinium-betaine
  参考文献：
  名称：

  Serebrjanyi, Ukrainskij Khimicheskij Zhurnal, 1957, vol. 23, p. 358,360

  摘要：

  DOI：
• 作为产物：
  描述：

  邻硝基苯乙醚 在 氢氧化钾 、 硫酸 作用下， 生成 9-ethylphenazin-1-ol
  参考文献：
  名称：

  Kiprianow; Krotschtschenko, Ukrainskij Khimicheskij Zhurnal, 1956, vol. 22, p. 351,354

  摘要：

  DOI：

文献信息

• An Efficient Buchwald–Hartwig/Reductive Cyclization for the Scaffold Diversification of Halogenated Phenazines: Potent Antibacterial Targeting, Biofilm Eradication, and Prodrug Exploration
  作者：Aaron T. Garrison、Yasmeen Abouelhassan、Dimitris Kallifidas、Hao Tan、Young S. Kim、Shouguang Jin、Hendrik Luesch、Robert W. Huigens

  DOI：10.1021/acs.jmedchem.7b01903

  日期：2018.5.10

  Bacterial biofilms are surface-attached communities comprised of nonreplicating persister cells housed within a protective extracellular matrix. Biofilms display tolerance toward conventional antibiotics, occur in ∼80% of infections, and lead to >500000 deaths annually. We recently identified halogenated phenazine (HP) analogues which demonstrate biofilm-eradicating activities against priority pathogens;

  细菌生物膜是由附着在保护性细胞外基质中的非复制性持久性细胞组成的表面附着群落。生物膜表现出对常规抗生素的耐受性，在约80％的感染中发生，每年导致> 500,000例死亡。我们最近鉴定了卤化吩嗪（HP）类似物，这些类似物证明了针对优先病原体的生物膜消除活性。然而，吩嗪的合成存在局限性。在此，我们报告了一种改进的HP合成方法，该方法可加快鉴定改良的生物膜消除剂的速度。1-甲氧基吩嗪支架是通过布赫瓦尔德-哈特维格交叉偶联（平均产率70％）和随后的还原环化（平均产率68％）生成的，从而加快了消灭强力生物膜的HP的发现（例如61：MRSA BAA-1707 MBEC = 4.69μM）。我们还开发了细菌选择性前药（还原活化的醌-烷氧基羰基氧基甲基部分），以提供HP 87，该产品显示出对MRSA BAA-1707（MIC = 0.15μM，MBEC = 12.5μM）具有出色的抗菌和生物膜根除活性。此
• Phenazine derivatives as antimicrobial agents
  申请人：University of Florida Research Foundation, Incorporated

  公开号：US11053205B2

  公开（公告）日：2021-07-06

  The present invention provides novel phenazine derivatives, such as compounds of Formula (I) (e.g., Formulae (II)-(XIX)), 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.

  本发明提供了新型吩嗪衍生物，如式(I)化合物（如式(II)-(XIX)）及其药学上可接受的盐类。本发明的化合物有望成为抗菌剂，并可通过微生物战争策略（如基于活性氧（ROS）的竞争策略）发挥作用。本发明还提供了涉及本发明化合物的药物组合物、试剂盒、用途和方法，可用于预防或治疗受试者的微生物感染（如细菌感染或分枝杆菌感染），抑制微生物（如细菌或分枝杆菌）的生长和/或繁殖、细菌或分枝杆菌）的生长和/或繁殖，杀死微生物（如细菌或分枝杆菌），抑制生物膜的形成和/或生长，减少或清除生物膜，和/或消毒表面。
• Serebrjanyi, Ukrainskij Khimicheskij Zhurnal, 1968, vol. 34, p. 805,809; engl. Ausg. S. Nr. 8, S. 44
  作者：Serebrjanyi

  DOI：——

  日期：——
• [EN] PHENAZINE DERIVATIVES AS ANTIMICROBIAL AGENTS<br/>[FR] DÉRIVÉS DE PHÉNAZINE UTILISÉS COMME AGENTS ANTIMICROBIENS
  申请人：UNIV OF RESEARCH FOUNDATION INCORPORATED

  公开号：WO2018152436A1

  公开（公告）日：2018-08-23

  The present invention provides novel phenazine derivatives, such as compounds of Formula (I) (e.g., Formulae (II) - (XIX)), 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.