3-(benzyloxy)-1-(2-(benzyloxy)ethyl)-4-oxo-1,4-dihydropyridine-2-carboxylic acid | 1219111-68-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡啶及其衍生物
• 英文名称: 3-(benzyloxy)-1-(2-(benzyloxy)ethyl)-4-oxo-1,4-dihydropyridine-2-carboxylic acid
• 英文别名: 1-(2-benzyloxyethyl)-3-benzyloxy-pyridin-4-(1H)-one-2-carboxylic acid；4-Oxo-3-phenylmethoxy-1-(2-phenylmethoxyethyl)pyridine-2-carboxylic acid
• CAS: 1219111-68-8
• 化学式: C₂₂H₂₁NO₅
• 分子量: 379.412
• InChiKey: XGZVGAZUJPTJCF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  28
• 可旋转键数：
  9
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  76.1
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  3-(benzyloxy)-1-(2-(benzyloxy)ethyl)-4-oxo-1,4-dihydropyridine-2-carboxylic acid 、 在 N-羟基丁二酰亚胺 、 N,N'-二环己基碳二亚胺 、 三乙胺 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 48.0h， 以68%的产率得到
  参考文献：
  名称：

  Design, Synthesis, and Antimicrobial Evaluation of Hexadentate Hydroxypyridinones with High Iron(III) Affinity

  摘要：

  A range of hexadentate 3‐hydroxypyridin‐4‐ones (HPOs) with high affinity for iron(III) has been synthesized. The log stability constants of two HPO–iron complexes (logK1) were determined to be over 34, and pFe values of the two HPOs were determined to be over 31. Antimicrobial assay indicated that they are able to markedly inhibit the growth of both Gram‐positive and Gram‐negative bacteria. Compounds 14a and 14e were found to exhibit the strongest inhibitory activity against Staphyloccocus aureus, Bacillus subtilis, Pseudomonas aeruginosa, and Escherichia coli, with MIC values of 8, 8, 16, and 8 μg/mL, respectively. These results indicate that hexadentate 3‐hydroxypyridin‐4‐ones have potential application as antimicrobial agents, especially in the treatment of wound infection.

  DOI：

  10.1111/cbdd.12358
• 作为产物：
  描述：

  3-(苄氧基)-2-甲基-4H-吡喃-4-酮 在 selenium(IV) oxide 、 sodium chlorite 、 氨基磺酸 、 乙酸酐 、 sodium hydride 、 溶剂黄146 、 sodium hydroxide 作用下， 以 四氢呋喃 、 甲醇 、 水 、 丙酮 为溶剂， 反应 5.5h， 生成 3-(benzyloxy)-1-(2-(benzyloxy)ethyl)-4-oxo-1,4-dihydropyridine-2-carboxylic acid
  参考文献：
  名称：

  Design, Synthesis, and Antimicrobial Evaluation of Hexadentate Hydroxypyridinones with High Iron(III) Affinity

  摘要：

  A range of hexadentate 3‐hydroxypyridin‐4‐ones (HPOs) with high affinity for iron(III) has been synthesized. The log stability constants of two HPO–iron complexes (logK1) were determined to be over 34, and pFe values of the two HPOs were determined to be over 31. Antimicrobial assay indicated that they are able to markedly inhibit the growth of both Gram‐positive and Gram‐negative bacteria. Compounds 14a and 14e were found to exhibit the strongest inhibitory activity against Staphyloccocus aureus, Bacillus subtilis, Pseudomonas aeruginosa, and Escherichia coli, with MIC values of 8, 8, 16, and 8 μg/mL, respectively. These results indicate that hexadentate 3‐hydroxypyridin‐4‐ones have potential application as antimicrobial agents, especially in the treatment of wound infection.

  DOI：

  10.1111/cbdd.12358

文献信息

• PROCESS FOR THE PREPARATION OF SUBSTITUTED PYRIDONE CARBOXYLIC ACIDS
  申请人：KULANGARA VIJAYA RAJ KUNIYIL

  公开号：US20100076199A1

  公开（公告）日：2010-03-25

  The present invention relates to methods for the preparation of pyridone carboxylic acids for use as intermediates in the preparation of various synthetic organic compounds. The pyridone carboxylic acids can for example be used as intermediates in the production of potent antitumor agents, antifungal agents, antiviral agents, psychotherapeutic agents or contrast imaging agents for MRI.

  本发明涉及用于制备吡啶酮羧酸的方法，用作合成各种有机化合物时的中间体。吡啶酮羧酸可以作为强效抗肿瘤药物、抗真菌药物、抗病毒药物、心理治疗药物或MRI对比成像剂的中间体。