5-cyano-1-ethyl-6,7-(methylenedioxy)-4-quinolone-3-carboxylic acid | 141613-50-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 喹啉及其衍生物
• 英文名称: 5-cyano-1-ethyl-6,7-(methylenedioxy)-4-quinolone-3-carboxylic acid
• 英文别名: 9-cyano-5-ethyl-8-oxo-[1,3]dioxolo[4,5-g]quinoline-7-carboxylic acid
• CAS: 141613-50-5
• 化学式: C₁₄H₁₀N₂O₅
• 分子量: 286.244
• InChiKey: JYXNOBMMKWSQFN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.32
• 重原子数：
  21.0
• 可旋转键数：
  2.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.21
• 拓扑面积：
  101.55
• 氢给体数：
  1.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  5-cyano-1-ethyl-6,7-(methylenedioxy)-4-quinolone-3-carboxylic acid 在 氯化亚砜 、 三溴化硼 、 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 28.0h， 生成 5-Cyano-1-ethyl-4-oxo-6,7-bis-trimethylsilanyloxy-1,4-dihydro-quinoline-3-carbonyl chloride
  参考文献：
  名称：

  Synthesis and structure-activity relationships of cephalosporins with C-3' catechol-containing residues

  摘要：

  Cephalosporins with new catechol substituents at C-3' have been synthesized, including novel compounds with C-3' carbon-carbon bonds. Many of these compounds have high potency against Gram-negative bacteria, in particular against resistant strains like Pseudomonas aeruginosa. Structure-activity relationships are discussed in terms of their dependence on the pK(a) of the C-3' catechol and also in terms of steric and conformational factors of the C-3' substituent. The best overall properties were found in compounds with a bulky and/or conformationally restricted acidic C-3' catechol.

  DOI：

  10.1021/jm00092a014
• 作为产物：
  描述：

  氰化钠 、 9-amino-5-ethyl-8-oxo-5,8-dihydro-[1,3]dioxolo[4,5-g]quinolin-7-carboxylic acid 在 nitrosylsulfuric acid 作用下， 生成 5-cyano-1-ethyl-6,7-(methylenedioxy)-4-quinolone-3-carboxylic acid
  参考文献：
  名称：

  Synthesis and structure-activity relationships of cephalosporins with C-3' catechol-containing residues

  摘要：

  Cephalosporins with new catechol substituents at C-3' have been synthesized, including novel compounds with C-3' carbon-carbon bonds. Many of these compounds have high potency against Gram-negative bacteria, in particular against resistant strains like Pseudomonas aeruginosa. Structure-activity relationships are discussed in terms of their dependence on the pK(a) of the C-3' catechol and also in terms of steric and conformational factors of the C-3' substituent. The best overall properties were found in compounds with a bulky and/or conformationally restricted acidic C-3' catechol.

  DOI：

  10.1021/jm00092a014