1-ethyl-6-fluoro-1,4-dihydro-4-oxo-7-(4-[ethoxycarbonylmethyl]-1-piperazinyl)-3-quinolinecarboxylic acid | 118476-20-3

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: 1-ethyl-6-fluoro-1,4-dihydro-4-oxo-7-(4-[ethoxycarbonylmethyl]-1-piperazinyl)-3-quinolinecarboxylic acid
• 英文别名: 1-Ethyl-6-fluoro-1,4-dihydro-7-<4-<(ethoxycarbonyl)methyl>-1-piperazinyl>-4-oxoquinoline-3-carboxylic Acid；7-(4-(2-ethoxy-2-oxoethyl)piperazin-1-yl)-1-ethyl-6-fluoro-4-oxo-1,4-dihydroquinoline-3-carboxylic acid；7-[4-(2-Ethoxy-2-oxoethyl)piperazin-1-yl]-1-ethyl-6-fluoro-4-oxoquinoline-3-carboxylic acid
• CAS: 118476-20-3
• 化学式: C₂₀H₂₄FN₃O₅
• 分子量: 405.426
• InChiKey: YIZBRGCMNUEGON-UHFFFAOYSA-N

物化性质

• 熔点：
  229-231 °C
• 沸点：
  591.3±50.0 °C(Predicted)
• 密度：
  1.322±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.6
• 重原子数：
  29
• 可旋转键数：
  7
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.45
• 拓扑面积：
  90.4
• 氢给体数：
  1
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  1-ethyl-6-fluoro-1,4-dihydro-4-oxo-7-(4-[ethoxycarbonylmethyl]-1-piperazinyl)-3-quinolinecarboxylic acid 在 间氯过氧苯甲酸 作用下， 以 氯仿 为溶剂， 反应 9.08h， 生成 诺氟沙星
  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：

  溴乙酸乙酯 、 诺氟沙星 在 sodium ethanolate 作用下， 以 乙醇 为溶剂， 反应 0.32h， 以98%的产率得到1-ethyl-6-fluoro-1,4-dihydro-4-oxo-7-(4-[ethoxycarbonylmethyl]-1-piperazinyl)-3-quinolinecarboxylic acid
  参考文献：
  名称：

  新型诺氟沙星-唑类杂合体的合成及抗菌活性评价

  摘要：

  摘要 以诺氟沙星为原料合成了诺氟沙星-唑类杂化物3和6a、b。用胺处理这些化合物作为一锅三组分反应产生相应的氨基衍生物 4a,b, 7a-g 和 8a,b，产率很高。使用常规方法和微波辅助方法，后一种方法更有效。合成化合物的结构通过元素分析、IR、1H NMR、13C NMR和MS表征。筛选所有化合物的抗微生物活性。它们中的大多数表现出优异的抗菌活性，但对选定的真菌没有活性。

  DOI：

  10.1515/hc-2018-0070

文献信息

• New Carbohydrate Derivatives of Norfloxacin
  作者：Virág Zsoldos‐Mády、Pál Sohár、József Kovács、István Pintér、Zoltán Szakács

  DOI：10.1081/car-200049410

  日期：2005.1

  New classes of sugar derivatives of the antibacterial drug norfloxacin (1) were synthesized by substituting the N-4' of the piperazinyl moiety of the molecule. Direct coupling with gluco- and galactopyranosyl units afforded glycosylamines 2-5. Introduction of urea or thiourea linkage between glycosyl and norfloxacin units was produced with the corresponding glycosyl isocyanates or isothiocyanates. For the synthesis of unprotected sugar urea compounds, a new approach was applied by using 1,2-N, O-carbonyl-beta-D-glycopyranoses. Hydrazinocarbonyl-methyl- and -propyl spacers also were found appropriate for linking norfloxacin with sugar units.
• 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：——
• Synthesis and antimicrobial activity evaluation of new norfloxacine-azole hybrids
  作者：Serpil Demirci、Neslihan Demirbaş、Meltem Menteşe、SerapBaşoğlu Özdemir、Şengül A. Karaoğlu

  DOI：10.1515/hc-2018-0070

  日期：2018.12.19

  The structures of the synthesized compounds were characterized by elemental analysis, IR, 1H NMR, 13C NMR and MS. All compounds were screened for their antimicrobial activities. Most of them exhibit excellent antibacterial activity but are not active against selected fungi.

  摘要 以诺氟沙星为原料合成了诺氟沙星-唑类杂化物3和6a、b。用胺处理这些化合物作为一锅三组分反应产生相应的氨基衍生物 4a,b, 7a-g 和 8a,b，产率很高。使用常规方法和微波辅助方法，后一种方法更有效。合成化合物的结构通过元素分析、IR、1H NMR、13C NMR和MS表征。筛选所有化合物的抗微生物活性。它们中的大多数表现出优异的抗菌活性，但对选定的真菌没有活性。
• Studies on prodrugs. 10. Possible mechanism of N-dealkylation of N-masked norfloxacins having several active methylene groups
  作者：Hirosato Kondo、Fumio Sakamoto、Yoshimasa Inoue、Goro Tsukamoto

  DOI：10.1021/jm00123a031

  日期：1989.3

  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.