3-(2-chloro-4-fluoro-5-nitrophenyl)-3-oxopropionic acid ethyl ester | 783357-48-2

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 3-(2-chloro-4-fluoro-5-nitrophenyl)-3-oxopropionic acid ethyl ester
• 英文别名: ethyl 3-(2-chloro-4-fluoro-5-nitrophenyl)-3-oxopropanoate
• CAS: 783357-48-2
• 化学式: C₁₁H₉ClFNO₅
• 分子量: 289.648
• InChiKey: VAVWDDRPNYAYGL-UHFFFAOYSA-N

物化性质

• 熔点：
  63-64 °C(Solv: cyclohexane (110-82-7); ethyl ether (60-29-7))
• 沸点：
  335.3±37.0 °C(Predicted)
• 密度：
  1.434±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  19
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.27
• 拓扑面积：
  89.2
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  3-(2-chloro-4-fluoro-5-nitrophenyl)-3-oxopropionic acid ethyl ester 在 sodium hydroxide 、 乙酸酐 、 potassium carbonate 作用下， 以 乙腈 为溶剂， 反应 5.0h， 生成 1-tert-butyl-1,4-dihydro-6-nitro-4-oxo-7-thiomorpholinoquinoline-3-carboxylic acid
  参考文献：
  名称：

  New 6-nitroquinolones: synthesis and antimicrobial activities

  摘要：

  Pursuing our searches on quinolonecarboxylic acids we used a simple three-step one pot procedure to synthesize novel 1,7-disubstituted-6-nitroquinolones. The new derivatives were tested against Mycobacterium tuberculosis and Mycobacterium avium complex (MAC) as well as against both gram-positive and gram-negative bacteria. In vitro assays showed some derivatives were endowed with good inhibiting activities against tested mycobacteria. Some derivatives were also found more potent than ciprofloxacin and ofloxacin (used as reference drugs) against gram-positive bacteria.

  DOI：

  10.1016/j.farmac.2004.01.014
• 作为产物：
  描述：

  2-氯-4-氟-5-硝基苯甲酸 在 氯化亚砜 、 三乙胺 、 magnesium chloride 作用下， 以 乙腈 为溶剂， 反应 4.5h， 生成 3-(2-chloro-4-fluoro-5-nitrophenyl)-3-oxopropionic acid ethyl ester
  参考文献：
  名称：

  New 6-nitroquinolones: synthesis and antimicrobial activities

  摘要：

  Pursuing our searches on quinolonecarboxylic acids we used a simple three-step one pot procedure to synthesize novel 1,7-disubstituted-6-nitroquinolones. The new derivatives were tested against Mycobacterium tuberculosis and Mycobacterium avium complex (MAC) as well as against both gram-positive and gram-negative bacteria. In vitro assays showed some derivatives were endowed with good inhibiting activities against tested mycobacteria. Some derivatives were also found more potent than ciprofloxacin and ofloxacin (used as reference drugs) against gram-positive bacteria.

  DOI：

  10.1016/j.farmac.2004.01.014

文献信息

• NOVEL COMPOSITIONS AND METHODS OF USE
  申请人：CHEN Huanming

  公开号：US20110269741A1

  公开（公告）日：2011-11-03

  Described herein are novel enzyme inhibitors. In some embodiments the enzyme inhibitors are integrase inhibitors, particularly HIV integrase inhibitors. Also described herein are compositions containing them and methods of using them. Thus, the compounds and compositions described herein are useful for the in vitro and in vivo inhibition of HIV integrase as a method of treating or preventing HIV, AIDS or related disorders.

  本文介绍了新型酶抑制剂。在某些实施例中，酶抑制剂是整合酶抑制剂，特别是HIV整合酶抑制剂。本文还介绍了包含它们的组合物和使用它们的方法。因此，本文所描述的化合物和组合物可用于体外和体内抑制HIV整合酶作为治疗或预防HIV、艾滋病或相关疾病的方法。
• [EN] NOVEL COMPOSITIONS AND METHODS OF USE<br/>[FR] NOUVELLES COMPOSITIONS ET PROCÉDÉS D'UTILISATION
  申请人：ARDEA BIOSCIENCES INC

  公开号：WO2009089263A3

  公开（公告）日：2009-09-17
• Nitroquinolones with broad-spectrum antimycobacterial activity in vitro
  作者：Marino Artico、Antonello Mai、Gianluca Sbardella、Silvio Massa、Chiara Musiu、Stefania Lostia、Francesca Demontis、Paolo La Colla

  DOI：10.1016/s0960-894x(99)00251-6

  日期：1999.6

  During search on quinolonecarboxylic acids we used a facile, convenient two- or three-step procedure to synthesize new quinolone analogs, bearing at the C-7 position alkylamino substituents, and at the C-6 position a fluorine or alternatively a nitro group. The new derivatives were tested against both Gram-positive and Gram-negative bacteria and against a number of different mycobacteria. In vitro assay's showed 1-tert-butyl-7-tert-butylamino-6-nitro-1,4-dihydro-4-quinolone-3-carboxylic acid to be a potent inhibitor of Streptococcus and Staphylococcus with potencies superior to those of ofloxacin and ciprofloxacin, used as reference drugs. Some 6-nitroquinolones were found to exert good inhibiting activities against Mycobacterium tuberculosis and various atypical mycobacteria, whereas the 6-fluoro counterparts showed poor or no activity against this bacterium. (C) 1999 Elsevier Science Ltd. All rights reserved.
• New 6-nitroquinolones: synthesis and antimicrobial activities
  作者：Gianluca Sbardella、Antonello Mai、Marino Artico、Maria Giovanna Setzu、Graziella Poni、Paolo La Colla

  DOI：10.1016/j.farmac.2004.01.014

  日期：2004.6

  Pursuing our searches on quinolonecarboxylic acids we used a simple three-step one pot procedure to synthesize novel 1,7-disubstituted-6-nitroquinolones. The new derivatives were tested against Mycobacterium tuberculosis and Mycobacterium avium complex (MAC) as well as against both gram-positive and gram-negative bacteria. In vitro assays showed some derivatives were endowed with good inhibiting activities against tested mycobacteria. Some derivatives were also found more potent than ciprofloxacin and ofloxacin (used as reference drugs) against gram-positive bacteria.