(Z)-3-Cyclopropylamino-2-(3-ethoxy-2,4,5-trifluoro-benzoyl)-acrylic acid ethyl ester | 1027303-55-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: (Z)-3-Cyclopropylamino-2-(3-ethoxy-2,4,5-trifluoro-benzoyl)-acrylic acid ethyl ester
• 英文别名: ethyl (Z)-3-(cyclopropylamino)-2-(3-ethoxy-2,4,5-trifluorobenzoyl)prop-2-enoate
• CAS: 1027303-55-4
• 化学式: C₁₇H₁₈F₃NO₄
• 分子量: 357.329
• InChiKey: CDMIDMJNPWUKPR-FLIBITNWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4
• 重原子数：
  25
• 可旋转键数：
  9
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.41
• 拓扑面积：
  64.6
• 氢给体数：
  1
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  (Z)-3-Cyclopropylamino-2-(3-ethoxy-2,4,5-trifluoro-benzoyl)-acrylic acid ethyl ester 在 镍 sodium hydroxide 、 硫酸 、 氢气 、 sodium hydride 、 potassium nitrate 作用下， 以 四氢呋喃 、 乙醇 为溶剂， 24.0~30.0 ℃ 、206.84 kPa 条件下， 反应 45.0h， 生成 5-amino-1-cyclopropyl-6,7-difluoro-1,4-dihydro-8-ethoxy-4-oxo-3-quinolinecarboxylic acid
  参考文献：
  名称：

  The Synthesis, Structure-Activity, and Structure-Side Effect Relationships of a Series of 8-Alkoxy- and 5-Amino-8-alkoxyquinolone Antibacterial Agents

  摘要：

  A series of 1-cyclopropyl-6-fluoro-8-alkoxy (8-methoxy and 8-ethoxy)-quionoline-3-carboxylic acids and 1-cyclopropyl-5-amino-6-fluoro-8-alkoxyquinoline-3-carboxylic acids has been prepared and evaluated for antibacterial activity. In addition, they were also compared to quinolones with classic substitution at C-8 (H, F, Cl) and the naphthyridine nucleus in a phototoxicity and mammalian cell cytotoxicity assay. The series of 8-methoxyquinolones had antibacterial activity against Gram-positive, Gram-negative, and anaerobic bacteria equivalent to the most active 8-substituted compounds (8-F and 8-Cl). There was also a concomitant reduction in several of the potential side effects (i.e., phototoxicity and clonogenicity) compared to the most active quinolones with classic substitution at C-8. The 8-ethoxy derivatives had an even better safety profile but were significantly less active (2-3 dilutions) in the antibacterial assay.

  DOI：

  10.1021/jm00022a013
• 作为产物：
  描述：

  2,4,5-三氟-3-羟基苯甲酸 在 2,2'-联吡啶 、 sodium hydroxide 、 正丁基锂 、 草酰氯 、 乙酸酐 、 sodium hydride 、 N,N-二甲基甲酰胺 作用下， 以 甲醇 、 乙醇 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 77.0h， 生成 (Z)-3-Cyclopropylamino-2-(3-ethoxy-2,4,5-trifluoro-benzoyl)-acrylic acid ethyl ester
  参考文献：
  名称：

  The Synthesis, Structure-Activity, and Structure-Side Effect Relationships of a Series of 8-Alkoxy- and 5-Amino-8-alkoxyquinolone Antibacterial Agents

  摘要：

  A series of 1-cyclopropyl-6-fluoro-8-alkoxy (8-methoxy and 8-ethoxy)-quionoline-3-carboxylic acids and 1-cyclopropyl-5-amino-6-fluoro-8-alkoxyquinoline-3-carboxylic acids has been prepared and evaluated for antibacterial activity. In addition, they were also compared to quinolones with classic substitution at C-8 (H, F, Cl) and the naphthyridine nucleus in a phototoxicity and mammalian cell cytotoxicity assay. The series of 8-methoxyquinolones had antibacterial activity against Gram-positive, Gram-negative, and anaerobic bacteria equivalent to the most active 8-substituted compounds (8-F and 8-Cl). There was also a concomitant reduction in several of the potential side effects (i.e., phototoxicity and clonogenicity) compared to the most active quinolones with classic substitution at C-8. The 8-ethoxy derivatives had an even better safety profile but were significantly less active (2-3 dilutions) in the antibacterial assay.

  DOI：

  10.1021/jm00022a013

文献信息

• The Synthesis, Structure-Activity, and Structure-Side Effect Relationships of a Series of 8-Alkoxy- and 5-Amino-8-alkoxyquinolone Antibacterial Agents
  作者：Joseph P. Sanchez、Rocco D. Gogliotti、John M. Domagala、Stephen J. Gracheck、Michael D. Huband、Josephine A. Sesnie、Michael A. Cohen、Martin A. Shapiro

  DOI：10.1021/jm00022a013

  日期：1995.10

  A series of 1-cyclopropyl-6-fluoro-8-alkoxy (8-methoxy and 8-ethoxy)-quionoline-3-carboxylic acids and 1-cyclopropyl-5-amino-6-fluoro-8-alkoxyquinoline-3-carboxylic acids has been prepared and evaluated for antibacterial activity. In addition, they were also compared to quinolones with classic substitution at C-8 (H, F, Cl) and the naphthyridine nucleus in a phototoxicity and mammalian cell cytotoxicity assay. The series of 8-methoxyquinolones had antibacterial activity against Gram-positive, Gram-negative, and anaerobic bacteria equivalent to the most active 8-substituted compounds (8-F and 8-Cl). There was also a concomitant reduction in several of the potential side effects (i.e., phototoxicity and clonogenicity) compared to the most active quinolones with classic substitution at C-8. The 8-ethoxy derivatives had an even better safety profile but were significantly less active (2-3 dilutions) in the antibacterial assay.