ethyl 3-(2,6-dichloro-5-fluoro-4-ethyl-pyrid-3-yl)-3-oxopropanoate | 132195-52-9

• 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: ethyl 3-(2,6-dichloro-5-fluoro-4-ethyl-pyrid-3-yl)-3-oxopropanoate
• 英文别名: Ethyl 3-(2,6-dichloro-4-ethyl-5-fluoropyridin-3-yl)-3-oxopropanoate
• CAS: 132195-52-9
• 化学式: C₁₂H₁₂Cl₂FNO₃
• 分子量: 308.137
• InChiKey: AISQSZXPBOQBRX-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  19
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.42
• 拓扑面积：
  56.3
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  ethyl 3-(2,6-dichloro-5-fluoro-4-ethyl-pyrid-3-yl)-3-oxopropanoate 在 乙酸酐 、 potassium carbonate 作用下， 以 乙醇 、 乙腈 为溶剂， 反应 17.0h， 生成 7-chloro-6-fluoro-5-ethyl-1-cyclopropyl-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：

  2,6-二氯-5-氟烟酸 在 五氯化磷 、 对甲苯磺酸 、 lithium diisopropyl amide 作用下， 反应 8.63h， 生成 ethyl 3-(2,6-dichloro-5-fluoro-4-ethyl-pyrid-3-yl)-3-oxopropanoate
  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。
• [EN] NAPHTHYRIDINE DERIVATIVES AS ANTIBACTERIAL AGENTS<br/>[FR] DERIVES DE NAPHTHYRIDINE COMME AGENTS ANTIBACTERIENS
  申请人：ABBOTT LAB

  公开号：WO2004083207A1

  公开（公告）日：2004-09-30

  Antibacterials having formula (I), 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.

  本文揭示了化学式(I)的抗菌剂及其盐、前药和前药盐，制备该化合物的过程以及用于该过程的中间体，含有该化合物的组合物，以及使用该化合物进行细菌感染的预防和治疗的方法。
• 5-Substituted-1,4-dihydro-4-oxonaphthyridine-3-carboxylate antibacterial agents
  申请人：Bristol-Myers Squibb Company

  公开号：EP0387802A2

  公开（公告）日：1990-09-19

  The invention is concerned with naphthyridine compounds of formula (I) which are substituted in the 7-position with various nitrogen heterocyclo groups and at the 1,3,4,5 and 6-positions with certain other groups. These compounds are antibacterial agents and are suitable for the treatment of infections.

  本发明涉及式（I）的萘啶化合物，该化合物在 7 位被各种氮杂环基团取代，在 1、3、4、5 和 6 位被某些其他基团取代。这些化合物是抗菌剂，适用于治疗感染。
• NAPHTHYRIDINE DERIVATIVES AS ANTIBACTERIAL AGENTS
  申请人：ABBOTT LABORATORIES

  公开号：EP1631570A1

  公开（公告）日：2006-03-08
• US8163769B2
  申请人：——

  公开号：US8163769B2

  公开（公告）日：2012-04-24