8-Fluoro-2-methyl-1,6-dioxo-9-[4-(2-trifluoromethyl-benzyl)-piperazin-1-yl]-2,3-dihydro-1H,6H-1λ4-thia-3a-aza-phenalene-5-carboxylic acid ethyl ester | 151295-36-2

• 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: 8-Fluoro-2-methyl-1,6-dioxo-9-[4-(2-trifluoromethyl-benzyl)-piperazin-1-yl]-2,3-dihydro-1H,6H-1λ4-thia-3a-aza-phenalene-5-carboxylic acid ethyl ester
• CAS: 151295-36-2
• 化学式: C₂₇H₂₇F₄N₃O₄S
• 分子量: 565.589
• InChiKey: WCMPPDNFKXYOHV-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.17
• 重原子数：
  39.0
• 可旋转键数：
  5.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.41
• 拓扑面积：
  71.85
• 氢给体数：
  0.0
• 氢受体数：
  7.0

反应信息

• 作为反应物：
  描述：

  8-Fluoro-2-methyl-1,6-dioxo-9-[4-(2-trifluoromethyl-benzyl)-piperazin-1-yl]-2,3-dihydro-1H,6H-1λ4-thia-3a-aza-phenalene-5-carboxylic acid ethyl ester 在 sodium hydroxide 、 三溴化磷 作用下， 以 乙醇 、 N,N-二甲基甲酰胺 为溶剂， 生成 7-Fluoro-3-methyl-10-oxo-6-[4-[[2-(trifluoromethyl)phenyl]methyl]piperazin-1-yl]-4-thia-1-azatricyclo[7.3.1.05,13]trideca-5(13),6,8,11-tetraene-11-carboxylic acid
  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：

  8-chloro-7-fluoro-2-methyl-3-oxo-3,4-dihydro-2H-1,4-benzothiazine 在 lithium aluminium tetrahydride 、 PPA 、 间氯过氧苯甲酸 作用下， 以 四氢呋喃 、 乙醇 、 N,N-二甲基甲酰胺 为溶剂， 反应 7.5h， 生成 8-Fluoro-2-methyl-1,6-dioxo-9-[4-(2-trifluoromethyl-benzyl)-piperazin-1-yl]-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