1-Ethyl-6-fluoro-7-(4-formyl-piperazin-1-yl)-4-oxo-1,2,3,4-tetrahydro-quinoline-3-carbaldehyde | 110719-53-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二嗪烷类
• 英文名称: 1-Ethyl-6-fluoro-7-(4-formyl-piperazin-1-yl)-4-oxo-1,2,3,4-tetrahydro-quinoline-3-carbaldehyde
• CAS: 110719-53-4
• 化学式: C₁₇H₂₀FN₃O₃
• 分子量: 333.363
• InChiKey: LBADRYSSZFFQPU-UHFFFAOYSA-N

物化性质

• 沸点：
  590.3±50.0 °C(Predicted)
• 密度：
  1.377±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.94
• 重原子数：
  24.0
• 可旋转键数：
  4.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.47
• 拓扑面积：
  60.93
• 氢给体数：
  0.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  1-Ethyl-6-fluoro-7-(4-formyl-piperazin-1-yl)-4-oxo-1,2,3,4-tetrahydro-quinoline-3-carbaldehyde 在 盐酸 、 manganese(IV) oxide 作用下， 以 甲醇 为溶剂， 反应 0.5h， 生成 1-乙基-6-氟-4-氧代-7-哌嗪-1-基喹啉-3-甲醛
  参考文献：
  名称：

  Studies on prodrugs. 7. Synthesis and antimicrobial activity of 3-formylquinolone derivatives

  摘要：

  Several 3-formylquinolone derivatives (8a-c) were synthesized to assay the antibacterial activity both in vitro and in vivo. In vitro, all of the compounds 8a-c showed lower activity than that of the corresponding 3-carboxyl compounds 1a-c, and in vivo, they showed higher activity than that of compounds 1a-c. After oral administration of 3-formyl compounds 8a-c to mice, the compounds were rapidly metabolized into 3-carboxyl compounds 1a-c. In particular, the 3-formyl derivative (8a) of norfloxacin (NFLX, 1a) gave a 2-fold higher serum level than that of NFLX and functioned as a prodrug of NFLX.

  DOI：

  10.1021/jm00396a035
• 作为产物：
  描述：

  诺氟沙星 在 sodium tetrahydroborate 、 sodium methylate 、 对甲苯磺酸 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 0.5h， 生成 1-Ethyl-6-fluoro-7-(4-formyl-piperazin-1-yl)-4-oxo-1,2,3,4-tetrahydro-quinoline-3-carbaldehyde
  参考文献：
  名称：

  Studies on prodrugs. 7. Synthesis and antimicrobial activity of 3-formylquinolone derivatives

  摘要：

  Several 3-formylquinolone derivatives (8a-c) were synthesized to assay the antibacterial activity both in vitro and in vivo. In vitro, all of the compounds 8a-c showed lower activity than that of the corresponding 3-carboxyl compounds 1a-c, and in vivo, they showed higher activity than that of compounds 1a-c. After oral administration of 3-formyl compounds 8a-c to mice, the compounds were rapidly metabolized into 3-carboxyl compounds 1a-c. In particular, the 3-formyl derivative (8a) of norfloxacin (NFLX, 1a) gave a 2-fold higher serum level than that of NFLX and functioned as a prodrug of NFLX.

  DOI：

  10.1021/jm00396a035