2-(ethoxymethylene)-3-(2,6-dichloro-3-fluoro-4-methyl-5-pyridinyl)-3-oxopropionic acid ethyl ester | 132195-45-0

• 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-(ethoxymethylene)-3-(2,6-dichloro-3-fluoro-4-methyl-5-pyridinyl)-3-oxopropionic acid ethyl ester
• 英文别名: ethyl (2E/Z)-2-((2,6-dichloro-5-fluoro-4-methylpyridin-3-yl)carbonyl)-3-ethoxy-2-propenoate；Ethyl 2-(2,6-dichloro-5-fluoro-4-methylpyridine-3-carbonyl)-3-ethoxyprop-2-enoate
• CAS: 132195-45-0
• 化学式: C₁₄H₁₄Cl₂FNO₄
• 分子量: 350.174
• InChiKey: YMDADPORKCZWPN-UHFFFAOYSA-N

物化性质

• 沸点：
  481.4±45.0 °C(Predicted)
• 密度：
  1.342±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.9
• 重原子数：
  22
• 可旋转键数：
  7
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  65.5
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  2-(ethoxymethylene)-3-(2,6-dichloro-3-fluoro-4-methyl-5-pyridinyl)-3-oxopropionic acid ethyl ester 在 sodium hydroxide 、 sodium hydride 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 作用下， 以 1,4-二氧六环 、 乙醇 、 乙腈 为溶剂， 反应 4.0h， 生成 7-((3S)-3-amino-1-pyrrolidinyl)-1,4,-dihydro-1-(2,4-difluorophenyl)-6-fluoro-5-methyl-4-oxo-1,8-napthyridine-3-carboxylic acid
  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， 反应 19.5h， 生成 2-(ethoxymethylene)-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

文献信息

• Antibacterial compounds
  申请人：——

  公开号：US20030232818A1

  公开（公告）日：2003-12-18

  Antibacterials having formula (I) 1 and salts, prodrugs, and salts of prodrugs thereof, processes for making the compounds and intermediates used in the processes, compositions containing the compounds, and methods of prophylaxis and treatment of bacterial infections using the compounds are disclosed.

  抗菌剂的化学式（I）及其盐、前药、前药的盐，制备这些化合物的方法和用于制备过程中使用的中间体，含有这些化合物的组合物，以及使用这些化合物进行细菌感染的预防和治疗方法被披露。
• Synthesis and Biological Activity of Novel N-1-Aryl-6-fluoro-5-methyl 1,8-Naphthyridine-3-carboxylic Acids
  作者：Jean-Pierre Jacquet、Daniel Bouzard、Pierre Di Cesare、Nicolas Dolnic、Massoud Massoudi、Philippe Remuzon

  DOI：10.3987/com-92-6121

  日期：——

  A series of 5-methyl-4-oxo-1,8-naphthyridine-3-carboxylic acids was prepared in which the N-1 position was substituted by various aryl groups. Seven compounds showed excellent in vitro antibacterial activity against Gram-positive and Gram-negative strains.