2-<<(1,1-dimethylethyl)amino>methylene>-3-(2,6-dichloro-3-fluoro-4-methyl-5-pyridinyl)-3-oxopropionic acid ethyl ester | 138668-29-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡啶及其衍生物
• 英文名称: 2-<<(1,1-dimethylethyl)amino>methylene>-3-(2,6-dichloro-3-fluoro-4-methyl-5-pyridinyl)-3-oxopropionic acid ethyl ester
• CAS: 138668-29-8
• 化学式: C₁₆H₁₉Cl₂FN₂O₃
• 分子量: 377.243
• InChiKey: APADPXDCUJNJMB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.85
• 重原子数：
  24.0
• 可旋转键数：
  5.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.44
• 拓扑面积：
  68.29
• 氢给体数：
  1.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  2-<<(1,1-dimethylethyl)amino>methylene>-3-(2,6-dichloro-3-fluoro-4-methyl-5-pyridinyl)-3-oxopropionic acid ethyl ester 在 sodium hydride 作用下， 以 1,4-二氧六环 为溶剂， 反应 1.0h， 以57%的产率得到7-chloro-6-fluoro-5-methyl-1-(1,1-dimethylethyl)-4-oxo-1,4-dihydro-1,8-naphthyridine-3-carboxylic acid ethyl ester
  参考文献：
  名称：

  Fluoronaphthyridines as antibacterial agents. 4. Synthesis and structure-activity relationships of 5-substituted 6-fluoro-7-(cycloalkylamino)-1,4-dihydro-4-oxo-1,8-naphthyridine-3-carboxylic acids

  摘要：

  A series of 5-substituted-6-fluoro-7-(cycloalkylamino)-1,4-dihydro-4-oxo-1,8-naphthyridine-3-carboxylic acids have been prepared and tested for their in vitro and in vivo antibacterial activities. The 5-methyl group gave better in vitro activity with the 1-cyclopropyl appendage, but poorer activity with the 1-tert-butyl moiety. With the 1-(2,4-difluorophenyl) substitution, the influence of the 7-cycloalkylamino group was determinant: a (3S)-3-amino-pyrrolidine was shown to enhance greatly the in vitro and in vivo activity of the 5-methyl derivative. Compound 33 (BMY 43748) was selected as a promising candidate for an improved therapeutic agent.

  DOI：

  10.1021/jm00081a013
• 作为产物：
  描述：

  2,6-Dichloro-5-fluoro-4-methyl-nicotinoyl chloride 在 乙酸酐 、 对甲苯磺酸 作用下， 以 乙醇 为溶剂， 反应 20.5h， 生成 2-<<(1,1-dimethylethyl)amino>methylene>-3-(2,6-dichloro-3-fluoro-4-methyl-5-pyridinyl)-3-oxopropionic acid ethyl ester
  参考文献：
  名称：

  Fluoronaphthyridines as antibacterial agents. 4. Synthesis and structure-activity relationships of 5-substituted 6-fluoro-7-(cycloalkylamino)-1,4-dihydro-4-oxo-1,8-naphthyridine-3-carboxylic acids

  摘要：

  A series of 5-substituted-6-fluoro-7-(cycloalkylamino)-1,4-dihydro-4-oxo-1,8-naphthyridine-3-carboxylic acids have been prepared and tested for their in vitro and in vivo antibacterial activities. The 5-methyl group gave better in vitro activity with the 1-cyclopropyl appendage, but poorer activity with the 1-tert-butyl moiety. With the 1-(2,4-difluorophenyl) substitution, the influence of the 7-cycloalkylamino group was determinant: a (3S)-3-amino-pyrrolidine was shown to enhance greatly the in vitro and in vivo activity of the 5-methyl derivative. Compound 33 (BMY 43748) was selected as a promising candidate for an improved therapeutic agent.

  DOI：

  10.1021/jm00081a013