1-acetoxymethylphenazine | 1088-38-6

• 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-acetoxymethylphenazine
• 英文别名: 1-Acetoxymethyl-phenazin；1-Phenazinemethanol, 1-acetate；phenazin-1-ylmethyl acetate
• CAS: 1088-38-6
• 化学式: C₁₅H₁₂N₂O₂
• 分子量: 252.272
• InChiKey: WSBBCSBLJHELAD-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.85
• 重原子数：
  19.0
• 可旋转键数：
  2.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.13
• 拓扑面积：
  52.08
• 氢给体数：
  0.0
• 氢受体数：
  4.0

反应信息

• 作为产物：
  描述：

  吩嗪-1-羧酸 在 吡啶 、 lithium aluminium tetrahydride 作用下， 以 甲醇 、 乙醚 为溶剂， 反应 1.0h， 生成 1-acetoxymethylphenazine
  参考文献：
  名称：

  Insights on the susceptibility of plant pathogenic fungi to phenazine-1-carboxylic acid and its chemical derivatives

  摘要：

  Pseudomonas chlororaphis subsp. aureofaciens strain M71 produced two phenazine compounds as main secondary metabolites. These metabolites were identified as phenazine-1-carboxylic acid (PCA) and 2-hydroxyphenazine (2-OH P). In this study, the spectrum of the activity of PCA and 2-OH P was evaluated against a group of crop and forestal plant pathogenic fungi by an agar plate bioassay. PCA was active against most of the tested plant pathogens, while 2-OH P slightly inhibited a few fungal species. Furthermore, four semisynthesised derivatives of PCA (phenazine-1-carboxymethyl, phenazine-1-carboxamide, phenazine-1-hydroxymethyl and phenazine-1-acetoxymethyl) were assayed for their antifungal activity against 11 phytopathogenic species. Results showed that the carboxyl group is a structural feature important for the antifungal activity of PCA. Since the activity of phenazine-1-carboxymethyl and phenazine-1-carboxamide, the two more lipophilic and reversible PCA derivatives remained substantially unaltered compared with PCA.

  DOI：

  10.1080/14786419.2012.696257