3-环丙基氨基-2-(2,6-二氯-5-氟吡啶-3-羰基)丙烯酸酯 | 96568-06-8

• 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
• 中文名称: 3-环丙基氨基-2-(2,6-二氯-5-氟吡啶-3-羰基)丙烯酸酯
• 英文名称: 3-cyclopropylamino-2-(2,6-dichloro-5-fluoropyridine-3-carbonyl) acrylate
• 英文别名: ethyl 2-(2,6-dichloro-5-fluoronicotinoyl)-3-cyclopropylaminoacrylate；ethyl 3-(cyclopropylamino)-2-(2,6-dichloro-5-fluoropyridine-3-carbonyl)prop-2-enoate
• CAS: 96568-06-8
• 化学式: C₁₄H₁₃Cl₂FN₂O₃
• 分子量: 347.173
• InChiKey: RAPUFVUTVQLBEW-UHFFFAOYSA-N

物化性质

• 沸点：
  491.9±45.0 °C(Predicted)
• 密度：
  1.44±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.91
• 重原子数：
  22.0
• 可旋转键数：
  6.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.36
• 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：

  3-环丙基氨基-2-(2,6-二氯-5-氟吡啶-3-羰基)丙烯酸酯 在 sodium hydroxide 、 potassium carbonate 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 作用下， 以 乙腈 为溶剂， 反应 3.0h， 生成 PD131628-00028
  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 、 乙酸酐 、 对甲苯磺酸 作用下， 以 乙醇 为溶剂， 反应 20.63h， 生成 3-环丙基氨基-2-(2,6-二氯-5-氟吡啶-3-羰基)丙烯酸酯
  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

• [EN] PROCESSES FOR PREPARING QUINOLONECARBOXYLATE DERIVATIVES<br/>[FR] PROCEDE DE PREPARATION DE DERIVES DE QUINOLONECARBOXYLATE
  申请人：YUHAN CORP

  公开号：WO2004056781A1

  公开（公告）日：2004-07-08

  The present invention provides a process for preparing quinolonecarboxylate derivatives under a mild condition in high yield, so as to be favorably applied to a large-scale mass production thereof.

  本发明提供了一种在温和条件下以高收率制备喹诺酮羧酸酯衍生物的方法，从而有利于其大规模量产的应用。
• Advantageous Use of Ionic Liquids for the Synthesis of Pharmaceutically Relevant Quinolones
  作者：Rolando Cannalire、Matteo Tiecco、Violetta Cecchetti、Raimondo Germani、Giuseppe Manfroni

  DOI：10.1002/ejoc.201800415

  日期：2018.6.22

  The use of ILs instead of DMF in the Grohe cycloaracylation for the synthesis of pharmaceutically relevant quinolones has several advantages. [TBMA][MsO] was the most favourable IL and was used in a one‐pot/three‐step procedure for the preparation of a quinolone acid by a totally green procedure. Our procedure represents an alternative approach to the industrial production of quinolones.

  在Grohe环酰化反应中使用IL代替DMF合成药物相关喹诺酮具有若干优势。[TBMA] [MsO]是最有利的IL，用于一锅/三步程序中，通过完全绿色的程序制备喹诺酮酸。我们的程序代表了喹诺酮类工业生产的替代方法。
• Antibacterial
  申请人：Dainippon Pharmaceutical Co., Ltd.

  公开号：US04649144A1

  公开（公告）日：1987-03-10

  The present invention relates to a 1,8-naphthyridine derivative of the formula ##STR1## wherein R.sub.1, R.sub.2 and R.sub.3 are the same or different and each hydrogen or lower alkyl having 1 to 5 carbon atoms; and esters thereof and salts thereof and processes for preparation thereof. These compounds show excellent antibacterial activity and are useful antibacterial agents.

  本发明涉及一种1,8-萘啶衍生物，其化学式为##STR1##其中R.sub.1，R.sub.2和R.sub.3相同或不同，每个为氢或具有1至5个碳原子的低级烷基；以及其酯和盐及其制备方法。这些化合物表现出优异的抗菌活性，是有用的抗菌剂。
• 6,7-disubstituted
  申请人：Bayer Aktiengesellschaft

  公开号：US04840954A1

  公开（公告）日：1989-06-20

  New 6,7-disubstituted-1-cyclopropyl-1,4-dihydro-4-oxo-1,8-naphthyridine-3-carb oxy lic acids of the formula (I) ##STR1## in which X represents halogen or nitro and A represents ##STR2## wherein R.sup.1, R.sup.2, R.sup.3 and R.sup.4 are defined hereinbelow are disclosed as well as their usefulness as antibacterial agents.

  公开了式(I)的新型6,7-二取代-1-环丙基-1,4-二氢-4-氧代-1,8-萘啶-3-羧酸，其中X代表卤素或硝基，A代表 ##STR2## 其中R.sup.1、R.sup.2、R.sup.3和R.sup.4的定义如下，以及它们作为抗菌剂的有用性。
• Processes for preparing quinolone carboxylate derivatives
  申请人：Lee Au Tai

  公开号：US20060058528A1

  公开（公告）日：2006-03-16

  Provided is a process for preparing quinolonecarboxylate derivatives under a mild condition in high yield, so as to be favorably applied to a large-scale mass production thereof.

  提供了一种在温和条件下高产得喹诺酮羧酸衍生物的制备过程，以便有利地应用于大规模生产。