ethyl 10-chloro-9-fluoro-2-methyl-7-oxo-2,3-dihydro-7H-pyrido<1,2,3-de><1,4>benzothiazine-6-carboxylate | 151295-22-6

• 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: ethyl 10-chloro-9-fluoro-2-methyl-7-oxo-2,3-dihydro-7H-pyrido<1,2,3-de><1,4>benzothiazine-6-carboxylate
• 英文别名: ethyl 9-fluoro-10-chloro-2-methyl-7-oxo-2,3-dihydro-7H-pyrido[1,2,3-de][ 1,4]benzothiazine-6-carboxylate；Ethyl 6-chloro-7-fluoro-3-methyl-10-oxo-4-thia-1-azatricyclo[7.3.1.05,13]trideca-5(13),6,8,11-tetraene-11-carboxylate
• CAS: 151295-22-6
• 化学式: C₁₅H₁₃ClFNO₃S
• 分子量: 341.791
• InChiKey: RCJVWJZFBIFZOM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  22
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  71.9
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  ethyl 10-chloro-9-fluoro-2-methyl-7-oxo-2,3-dihydro-7H-pyrido<1,2,3-de><1,4>benzothiazine-6-carboxylate 在 间氯过氧苯甲酸 作用下， 以 乙醇 、 N,N-二甲基甲酰胺 为溶剂， 反应 4.0h， 生成 8-Fluoro-9-(4-formyl-piperazin-1-yl)-2-methyl-1,6-dioxo-2,3-dihydro-1H,6H-1λ4-thia-3a-aza-phenalene-5-carboxylic acid ethyl ester
  参考文献：
  名称：

  Quinolinecarboxylic acids. 3. Synthesis and antibacterial evaluation of 2-substituted 7-oxo-2,3-dihydro-7H-pyrido[1,2,3-de][1,4]benzothiazine-6-carboxylic acids related to rufloxacin

  摘要：

  A series of 2-substituted-7-oxo-2,3-dihydro-7H-pyrido[1,2,3-de][1,4]benzothiazine-6-carboxylic acids has been prepared and evaluated for in vitro antibacterial activity. These derivatives were less active than corresponding desmethylated analogues. Among these derivatives, the most active compound 22a was selected for preliminary pharmacokinetics in rats. The pharmacokinetic data indicated that 22a was rapidly absorbed and induced lasting plasma and urinary levels. In comparison with rufloxacin, it was excreted in low quantity in urine; a significant amount of desmethylated piperazinyl urinary metabolite was observed.

  DOI：

  10.1021/jm00074a028
• 作为产物：
  描述：

  3-氯-2,4-二氟硝基苯 在 ammonium hydroxide 、 sodium hydroxide 、 lithium aluminium tetrahydride 、 PPA 、 iron(II) sulfate 作用下， 以 四氢呋喃 、 水 、 二甲基亚砜 为溶剂， 反应 14.75h， 生成 ethyl 10-chloro-9-fluoro-2-methyl-7-oxo-2,3-dihydro-7H-pyrido<1,2,3-de><1,4>benzothiazine-6-carboxylate
  参考文献：
  名称：

  Quinolinecarboxylic acids. 3. Synthesis and antibacterial evaluation of 2-substituted 7-oxo-2,3-dihydro-7H-pyrido[1,2,3-de][1,4]benzothiazine-6-carboxylic acids related to rufloxacin

  摘要：

  A series of 2-substituted-7-oxo-2,3-dihydro-7H-pyrido[1,2,3-de][1,4]benzothiazine-6-carboxylic acids has been prepared and evaluated for in vitro antibacterial activity. These derivatives were less active than corresponding desmethylated analogues. Among these derivatives, the most active compound 22a was selected for preliminary pharmacokinetics in rats. The pharmacokinetic data indicated that 22a was rapidly absorbed and induced lasting plasma and urinary levels. In comparison with rufloxacin, it was excreted in low quantity in urine; a significant amount of desmethylated piperazinyl urinary metabolite was observed.

  DOI：

  10.1021/jm00074a028

文献信息

• Antibacterially active pyrido-benzothiazine derivatives with long term action
  申请人：MEDIOLANUM FARMACEUTICI s.r.l.

  公开号：EP0267432B1

  公开（公告）日：1991-12-27
• US4868299A
  申请人：——

  公开号：US4868299A

  公开（公告）日：1989-09-19
• Quinolinecarboxylic acids. 3. Synthesis and antibacterial evaluation of 2-substituted 7-oxo-2,3-dihydro-7H-pyrido[1,2,3-de][1,4]benzothiazine-6-carboxylic acids related to rufloxacin
  作者：Violetta Cecchetti、Arnaldo Fravolini、Pier Giuseppe Pagella、Angela Savino、Oriana Tabarrini

  DOI：10.1021/jm00074a028

  日期：1993.10

  A series of 2-substituted-7-oxo-2,3-dihydro-7H-pyrido[1,2,3-de][1,4]benzothiazine-6-carboxylic acids has been prepared and evaluated for in vitro antibacterial activity. These derivatives were less active than corresponding desmethylated analogues. Among these derivatives, the most active compound 22a was selected for preliminary pharmacokinetics in rats. The pharmacokinetic data indicated that 22a was rapidly absorbed and induced lasting plasma and urinary levels. In comparison with rufloxacin, it was excreted in low quantity in urine; a significant amount of desmethylated piperazinyl urinary metabolite was observed.