6-Nitro-7-methyl-1-ethyl-3-ethoxycarbonyl-4-hydroxy-1,2-dihydro-1,8-naphthyridin | 57018-74-3

• 分子结构分类: 有机化合物 - 有机1,3-偶极化合物 - 烯丙基型1,3-偶极有机化合物
• 英文名称: 6-Nitro-7-methyl-1-ethyl-3-ethoxycarbonyl-4-hydroxy-1,2-dihydro-1,8-naphthyridin
• 英文别名: 1-ethyl-7-methyl-6-nitro-4-oxo-1,2,3,4-tetrahydro-[1,8]naphthyridine-3-carboxylic acid ethyl ester
• CAS: 57018-74-3
• 化学式: C₁₄H₁₇N₃O₅
• 分子量: 307.306
• InChiKey: MNSJNHWFEZKPED-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.97
• 重原子数：
  22.0
• 可旋转键数：
  4.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.43
• 拓扑面积：
  105.8
• 氢给体数：
  1.0
• 氢受体数：
  7.0

反应信息

• 作为反应物：
  描述：

  6-Nitro-7-methyl-1-ethyl-3-ethoxycarbonyl-4-hydroxy-1,2-dihydro-1,8-naphthyridin 在 palladium on activated charcoal 盐酸 、 tetrafluoroboric acid 、 selenium(IV) oxide 、 氢气 、 2,3-二氯-5,6-二氰基-1,4-苯醌 、 sodium nitrite 作用下， 以 1,4-二氧六环 、 溶剂黄146 为溶剂， 25.0~175.0 ℃ 、368.86 kPa 条件下， 反应 21.0h， 生成 1-ethyl-6-fluoro-7-formyl-1,4-dihydro-4-oxo-1,8-naphthyridine-3-carboxylic acid
  参考文献：
  名称：

  New structure-activity relationships of the quinolone antibacterials using the target enzyme. The development and application of a DNA gyrase assay

  摘要：

  A series of 60 newly synthesized and known quinolone antibacterials, including quinoline- and 1,8-naphthyridine-3-carboxylic acids, pyrido[2,3-d]pyrimidine-6-carboxylic acids, and some monocyclic 4-pyridone-3-carboxylic acids, were tested and compared in a newly established, easy to perform, DNA gyrase assay. The results were correlated with minimum inhibitory concentrations (MICs) against a variety of organisms. Among the known quinolones were 14 clinically significant drugs (oxolinic acid, norfloxacin, ciprofloxacin, enoxacin, etc.) which were used as standards and compared side-by-side. The study focused on the changes in DNA gyrase inhibition brought about by certain features of the molecules, namely, the C6-fluorine or the nature of the C7 substituent. The intrinsic gyrase inhibition of the fused parent rings, quinoline vs. naphthyridine vs. pyrido[2,3-d]pyrimidine, was also explored. In all cases, loss of enzyme inhibition produced poor MICs, but some compounds with good DNA gyrase inhibition did not correspondingly inhibit bacterial growth. Possible explanations for this phenomena and the benefits of a DNA gyrase-MIC strategy for developing future structure-activity relationships are discussed.

  DOI：

  10.1021/jm00153a015