1-carbomethoxy-7-methoxy-phenazine | 73113-71-0

• 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: 1-carbomethoxy-7-methoxy-phenazine
• 英文别名: methyl 7-methoxyphenazine-1-carboxylate；7-Methoxyphenazin-1-carbonsaeuremethylester；7-methoxy-phenazine-1-carboxylic acid methyl ester
• CAS: 73113-71-0
• 化学式: C₁₅H₁₂N₂O₃
• 分子量: 268.272
• InChiKey: ODQWLBQFOQTWHZ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  20
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.13
• 拓扑面积：
  61.3
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  1-carbomethoxy-7-methoxy-phenazine 在 水 、 sodium hydroxide 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 反应 2.0h， 以86%的产率得到7-methoxyphenazine-1-carboxylic acid
  参考文献：
  名称：

  Synthesis, biological evaluation, and metabolic stability of phenazine derivatives as antibacterial agents

  摘要：

  Drug-resistant pathogens are a major cause of hospital- and community-associated bacterial infections in the United States and around the world. These infections are increasingly difficult to treat due to the development of antibiotic resistance and the formation of bacterial biofilms. In the paper, a series of phenazines were synthesized and evaluated for their in vitro antimicrobial activity against Gram positive (methicillin resistant staphylococcus aureus, MRSA) and Gram negative (Escherichia coli, E. coli) bacteria. The compound 6,9-dichloro-N-(methylsulfonyl)phenazine-l-carboxamide (18c) proved to be the most active molecule (MIC = 16 mu g/mL) against MRSA whereas 9-methyl-N-(methylsulfonyl)phenazine-1-carboxamide (30e) showed good activity against both MRSA (MIC = 32 mu g/mL) and E. coli (MIC = 32 mu g/mL). Molecule 18c also demonstrated significant biofilm dispersion and inhibition against S. aureus. Preliminary studies indicate the molecules do not disturb bacterial membranes and there activity is not directly linked to the generation of reactive oxygen species. Compound 18c displayed minor toxicity against mammalian cells. Metabolic stability studies of the most promising compounds indicate stability towards phase I and phase II metabolizing enzymes. (C) 2017 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2017.11.026
• 作为产物：
  描述：

  2-溴-3-硝基苯甲酸甲酯 在 palladium on activated charcoal 氢气 、 溴 、 palladium diacetate 、 碳酸氢钠 、 caesium carbonate 、 R-(+)-1,1'-联萘-2,2'-双二苯膦 作用下， 以 氯仿 、 乙酸乙酯 、 甲苯 为溶剂， 生成 1-carbomethoxy-7-methoxy-phenazine
  参考文献：
  名称：

  吩嗪的新途径†

  摘要：

  通过钯（II）催化的芳基溴化物8的分子内胺化反应制备吩嗪，这些芳基溴化物是由邻溴代硝基苯3和苯胺4或3和邻溴代苯胺5使用钯（II）催化的苯胺芳基化反应制备的。

  DOI：

  10.1016/s0040-4039(99)02061-4

文献信息

• Synthesis, biological evaluation, and metabolic stability of phenazine derivatives as antibacterial agents
  作者：Maddeboina Krishnaiah、Nathalia Rodrigues de Almeida、Venkatareddy Udumula、Zhongcheng Song、Yashpal Singh Chhonker、Mai M. Abdelmoaty、Valter Aragao do Nascimento、Daryl J. Murry、Martin Conda-Sheridan

  DOI：10.1016/j.ejmech.2017.11.026

  日期：2018.1

  Drug-resistant pathogens are a major cause of hospital- and community-associated bacterial infections in the United States and around the world. These infections are increasingly difficult to treat due to the development of antibiotic resistance and the formation of bacterial biofilms. In the paper, a series of phenazines were synthesized and evaluated for their in vitro antimicrobial activity against Gram positive (methicillin resistant staphylococcus aureus, MRSA) and Gram negative (Escherichia coli, E. coli) bacteria. The compound 6,9-dichloro-N-(methylsulfonyl)phenazine-l-carboxamide (18c) proved to be the most active molecule (MIC = 16 mu g/mL) against MRSA whereas 9-methyl-N-(methylsulfonyl)phenazine-1-carboxamide (30e) showed good activity against both MRSA (MIC = 32 mu g/mL) and E. coli (MIC = 32 mu g/mL). Molecule 18c also demonstrated significant biofilm dispersion and inhibition against S. aureus. Preliminary studies indicate the molecules do not disturb bacterial membranes and there activity is not directly linked to the generation of reactive oxygen species. Compound 18c displayed minor toxicity against mammalian cells. Metabolic stability studies of the most promising compounds indicate stability towards phase I and phase II metabolizing enzymes. (C) 2017 Elsevier Masson SAS. All rights reserved.
• A new route to phenazines
  作者：Takahiro Emoto、Nobuo Kubosaki、Yoshiro Yamagiwa、Tadao Kamikawa

  DOI：10.1016/s0040-4039(99)02061-4

  日期：2000.1

  Phenazines were prepared by the palladium(II)-catalyzed intramolecular amination of aryl bromides 8, which were prepared with o-bromonitrobenzenes 3 and anilines 4 or 3 and o-bromoanilines 5 using palladium(II)-catalyzed aniline arylation.

  通过钯（II）催化的芳基溴化物8的分子内胺化反应制备吩嗪，这些芳基溴化物是由邻溴代硝基苯3和苯胺4或3和邻溴代苯胺5使用钯（II）催化的苯胺芳基化反应制备的。

表征谱图