1-ethyl-6-fluoro-1,4-dihydro-4-oxo-7-[4-(2-oxopropyl)-1-piperazinyl]-quinoline-3-carboxylic acid | 103175-73-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 喹啉及其衍生物
• 英文名称: 1-ethyl-6-fluoro-1,4-dihydro-4-oxo-7-[4-(2-oxopropyl)-1-piperazinyl]-quinoline-3-carboxylic acid
• 英文别名: 1-ethyl-6-fluoro-1,4-dihydro-4-oxo-7-<4-(2-oxopropyl)-1-piperazinyl>quinoline-3-carboxylic acid；1-ethyl-6-fluoro-1,4-dihydro-4-oxo-7-[4-(2-oxopropyl)-1-piperazinyl]quinoline-3-carboxylic acid；1-ET-6-F-4-OXO-7-(4-(2-OXO-PR)-PIPERAZIN-1-YL)-2H-QUINOLINE-3-CARBOXYLIC ACID；3-Quinolinecarboxylic acid, 1,4-dihydro-1-ethyl-6-fluoro-4-oxo-7-(4-(2-oxopropyl)-1-piperazinyl)-；1-ethyl-6-fluoro-4-oxo-7-[4-(2-oxopropyl)piperazin-1-yl]quinoline-3-carboxylic acid
• CAS: 103175-73-1
• 化学式: C₁₉H₂₂FN₃O₄
• 分子量: 375.4
• InChiKey: SOYKHROCYAGPMS-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0
• 重原子数：
  27
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.42
• 拓扑面积：
  81.2
• 氢给体数：
  1
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  1-ethyl-6-fluoro-1,4-dihydro-4-oxo-7-[4-(2-oxopropyl)-1-piperazinyl]-quinoline-3-carboxylic acid 在 间氯过氧苯甲酸 作用下， 以 氯仿 为溶剂， 生成
  参考文献：
  名称：

  Studies on prodrugs. 10. Possible mechanism of N-dealkylation of N-masked norfloxacins having several active methylene groups

  摘要：

  As a prodrug approach to norfloxacin (NFLX, 2), we have prepared several N-masked NFLXs (1a-f) and studied the cleavage mechanism of the C-N bond of N-masked NFLXs utilizing the following experiments: (1) the oxidation of N-masked NFLXs (1a-f) with m-chloroperbenzoic acid (MCPBA) and their subsequent cleavage to 2 in chloroform at room temperature or at 50 degrees C; (2) the liberation of NFLX from N-masked NFLXs after oral administration in mice. It was found that the chemical oxidative dealkylation of N-masked NFLXs proceeded when anion-stabilizing groups (e.g., CN, COR, COOR) are present on the alpha carbon of the nitrogen atom. In in vivo experiments, N-masked NFLXs having acidic hydrogens on the alpha carbon to the nitrogen atom also liberated NFLX (2) after oral administration.

  DOI：

  10.1021/jm00123a031
• 作为产物：
  描述：

  诺氟沙星 、 溴丙酮 在 potassium hydrogencarbonate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 1.0h， 以68%的产率得到1-ethyl-6-fluoro-1,4-dihydro-4-oxo-7-[4-(2-oxopropyl)-1-piperazinyl]-quinoline-3-carboxylic acid
  参考文献：
  名称：

  Studies on prodrugs. 5. Synthesis and antimicrobial activity of N-(oxoalkyl)norfloxacin derivatives

  摘要：

  Several N-(oxoalkyl)norfloxacin derivatives (3a-g) were synthesized and evaluated for antibacterial activity in vitro and in vivo. Most of the compounds exhibited in vitro activity comparable to that of norfloxacin for Gram-positive bacteria, whereas their activity was lower than for Gram-negative bacteria. N-(2-Oxopropyl)norfloxacin (3b) liberated norfloxacin in the blood after oral administration in mice, and the serum level of norfloxacin was about 3-fold higher than that of norfloxacin itself. Thus, 3b showed high antibacterial activity in vivo.

  DOI：

  10.1021/jm00160a037

文献信息

• 6-fluoro-1,4-dihydro-7-[4-(2-hydroxyiminoethyl)-1-piperazinyl]-4-oxoquinoline-3-carboxylic acid derivatives, their preparation and pharmaceutical compositions
  申请人：Pharmaceutical Industry Technology

  公开号：US20020061895A1

  公开（公告）日：2002-05-23

  The present invention discloses a novel 6-fluoro-1,4-dihydro-7-[4-(2-hydroxyiminoethyl)-1-piperazinyl]-4-oxoquinoline-3-carboxylic acid derivatives (formula I), with a process for their preparation, and with pharmaceutical compositions containing them as the active ingredient for the treatment of bacterial infections and/or renal cancer diseases. 1

  本发明揭示了一种新颖的6-氟-1,4-二氢-7-[4-(2-羟基亚胺基乙基)-1-哌嗪基]-4-氧喹啉-3-羧酸衍生物（式I），以及它们的制备方法和含有它们作为活性成分的药物组合物，用于治疗细菌感染和/或肾癌疾病。
• 6-fluoro-1,4-dihydro-7-&lsqb;4-(2-hydroxyiminoethyl)-1-piperazinyl&rsqb;-4-oxoquinoline-3-carboxylic acid derivatives, their preparation and pharmaceutical compositions
  申请人：Pharmaceutical Industry Technology and Development Center

  公开号：US06492373B2

  公开（公告）日：2002-12-10

  The present invention discloses a novel 6-fluoro-1,4-dihydro-7-[4-(2-hydroxyiminoethyl)-1-piperazinyl]-4-oxoquinoline-3-carboxylic acid derivatives (formula I), with a process for their preparation, and with pharmaceutical compositions containing them as the active ingredient for the treatment of bacterial infections and/or renal cancer diseases.

  本发明揭示了一种新型的6-氟-1,4-二氢-7-[4-(2-羟基亚胺乙基)-1-哌嗪基]-4-氧代喹啉-3-羧酸衍生物（式I），其制备过程以及含有它们作为活性成分的药物组合物，用于治疗细菌感染和/或肾癌疾病。
• Synthesis, Antibacterial, and Cytotoxic Evaluation of Certain 7-Substituted Norfloxacin Derivatives
  作者：Kuo-Chang Fang、Yeh-Long Chen、Jia-Yuh Sheu、Tai-Chi Wang、Cherng-Chyi Tzeng

  DOI：10.1021/jm000153x

  日期：2000.10.1

  We report herein the synthesis and biological evaluation of two series of 7-substituted norfloxacin derivatives. Most compounds tested in this study demonstrated better activity against methicillin-resistant Staphylococcus aureus than norfloxacin. Preliminary in vitro evaluation indicated that the 7-[4-(2-hydroxyiminoethyl)piperazin-1-yl] derivatives 3b-e possess distinct cytotoxicity profiles as compared with their alpha-methylene-gamma-butyrolactone counterparts, 4b,e: i.e., excellent activities against the renal cancer subpanel. Among them, 1-ethyl-6-fluoro-7-4-[2-(4-chlorophenyl)-2-hydroxyiminoethyl]-1-piperazinyl}-4-oxo-1,4-dihydro-3-quinolinecarboxylic acid (3d) demonstrated the most significant activities against renal cancer cell lines, with log GI(50) values of -6.40 against CAK-1, -6.14 against RXF 393, and -7.54 against UO-31, compared with a mean log GI(50) value of -5.03.
• KONDO, HIROSATO;SAKAMOTO, FUMIO;INOUE, YOSHIMASA;TSUKAMOTO, GORO, J. MED. CHEM., 32,(1989) N, C. 679-682
  作者：KONDO, HIROSATO、SAKAMOTO, FUMIO、INOUE, YOSHIMASA、TSUKAMOTO, GORO

  DOI：——

  日期：——
• US6492373B2
  申请人：——

  公开号：US6492373B2

  公开（公告）日：2002-12-10