9-chloro-N-cyanophenazine-1-carboxamide

• 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-chloro-N-cyanophenazine-1-carboxamide
• 化学式: C₁₄H₇ClN₄O
• 分子量: 282.689
• InChiKey: MOCGYVCSXCZGLS-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  20
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  78.7
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  氰胺 、 9-氯吩嗪-1-羧酸 在 4-二甲氨基吡啶 、 N,N'-羰基二咪唑 、 三乙胺 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 26.0h， 以49%的产率得到9-chloro-N-cyanophenazine-1-carboxamide
  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

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.