7-(4-(3-azidopropyl)piperazin-1-yl)-1-cyclopropyl-6-fluoro-4-oxo-1,4-dihydroquinoline-3-carboxylic acid | 1144106-71-7

• 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: 7-(4-(3-azidopropyl)piperazin-1-yl)-1-cyclopropyl-6-fluoro-4-oxo-1,4-dihydroquinoline-3-carboxylic acid
• 英文别名: 7-[4-(3-Azidopropyl)piperazin-1-yl]-1-cyclopropyl-6-fluoro-4-oxoquinoline-3-carboxylic acid
• CAS: 1144106-71-7
• 化学式: C₂₀H₂₃FN₆O₃
• 分子量: 414.439
• InChiKey: RMXXISWNSRPUDO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.6
• 重原子数：
  30
• 可旋转键数：
  7
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  78.4
• 氢给体数：
  1
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  2-(7-(dimethylamino)-2-oxo-2H-chromen-4-yl)-N-(prop-2-yn-1-yl)acetamide 、 7-(4-(3-azidopropyl)piperazin-1-yl)-1-cyclopropyl-6-fluoro-4-oxo-1,4-dihydroquinoline-3-carboxylic acid 在 copper(II) sulfate 作用下， 以 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 1.0h， 以12%的产率得到1-Cyclopropyl-7-[4-[3-[4-[[[2-[7-(dimethylamino)-2-oxochromen-4-yl]acetyl]amino]methyl]triazol-1-yl]propyl]piperazin-1-yl]-6-fluoro-4-oxoquinoline-3-carboxylic acid
  参考文献：
  名称：

  氟喹诺酮衍生的荧光探针，用于研究细菌的渗透和外排。

  摘要：

  使用Cu（i）催化的叠氮化物-炔烃环加成（CuAAC）合成了衍生自氟喹诺酮抗生素环丙沙星的荧光探针，以将环丙沙星叠氮化物衍生物与炔烃取代的绿色和蓝色荧光团连接。叠氮化物（2）和荧光团（3和4）衍生物保留了对革兰氏阳性和革兰氏阴性细菌的抗菌活性。共聚焦荧光显微镜的使用显示了细胞内的渗透，在存在作为大肠杆菌外排泵抑制剂的羰基氰3-氯苯基phenyl的情况下，细胞内的渗透显着增强。

  DOI：

  10.1039/c9md00124g
• 作为产物：
  描述：

  环丙沙星 、 alkaline earth salt of/the/ methylsulfuric acid 在 碳酸氢钠 作用下， 以 乙腈 为溶剂， 以70%的产率得到7-(4-(3-azidopropyl)piperazin-1-yl)-1-cyclopropyl-6-fluoro-4-oxo-1,4-dihydroquinoline-3-carboxylic acid
  参考文献：
  名称：

  Design, Synthesis, and Evaluation of Novel Fluoroquinolone−Aminoglycoside Hybrid Antibiotics

  摘要：

  A series of new hybrid structures containing fluoroquinolone (ciprofloxacin) and aminoglycoside (neomycin) antibiotics linked via 1,2,3-triazole moiety were designed and synthesized, and their antibacterial activities were determined against both Gram-negative and Gram-positive bacteria, including resistant strains. The nature of spacers in both the ciprofloxacin and neomycin parts greatly influenced the antibacterial activity. The majority of hybrids was significantly more potent than the parent neomycin and overcame most prevalent types of resistance associated with aminoglycosides. Selected hybrids inhibited bacterial protein synthesis with the potencies similar to or better than that of neomycin and were up to 32-fold more potent inhibitors than ciprofloxacin for the fluoroquinolone targets, DNA gyrase and toposiomerase IV, indicating a balanced dual mode of action. Significant delay of resistance formation was observed in both E. coli and B. subtilis to the treatment with ciprofloxacin-neomycin hybrid in comparison to that of each drug separately or their 1: 1 mixture.

  DOI：

  10.1021/jm900028n

文献信息

• CONJUGATED ANTIMICROBIAL AGENTS
  申请人：Technion Research & Development Foundation Ltd.

  公开号：EP2413974A1

  公开（公告）日：2012-02-08
• US8809286B2
  申请人：——

  公开号：US8809286B2

  公开（公告）日：2014-08-19
• US9149536B2
  申请人：——

  公开号：US9149536B2

  公开（公告）日：2015-10-06
• [EN] CONJUGATED ANTIMICROBIAL AGENTS<br/>[FR] AGENTS ANTIMICROBIENS CONJUGUÉS
  申请人：TECHNION RES & DEV FOUNDATION

  公开号：WO2010113151A1

  公开（公告）日：2010-10-07

  Provided herein are antimicrobial conjugates of two antibiotic agents, exhibiting improved activity also against resistant bacteria, compared to each of the agents separately or their mixture, and having substantially no resistance emerged thereagainst, as well as processes for preparation the same, compositions containing the same, and uses thereof in medical treatments against pathogenic microorganisms. The disclosed antimicrobial conjugates are composed of aminoglycosides and non-ribosomal active antibiotics. Some of the antimicrobial conjugates are prepared via "click" chemistry.
• Design, Synthesis, and Evaluation of Novel Fluoroquinolone−Aminoglycoside Hybrid Antibiotics
  作者：Varvara Pokrovskaya、Valery Belakhov、Mariana Hainrichson、Sima Yaron、Timor Baasov

  DOI：10.1021/jm900028n

  日期：2009.4.23

  A series of new hybrid structures containing fluoroquinolone (ciprofloxacin) and aminoglycoside (neomycin) antibiotics linked via 1,2,3-triazole moiety were designed and synthesized, and their antibacterial activities were determined against both Gram-negative and Gram-positive bacteria, including resistant strains. The nature of spacers in both the ciprofloxacin and neomycin parts greatly influenced the antibacterial activity. The majority of hybrids was significantly more potent than the parent neomycin and overcame most prevalent types of resistance associated with aminoglycosides. Selected hybrids inhibited bacterial protein synthesis with the potencies similar to or better than that of neomycin and were up to 32-fold more potent inhibitors than ciprofloxacin for the fluoroquinolone targets, DNA gyrase and toposiomerase IV, indicating a balanced dual mode of action. Significant delay of resistance formation was observed in both E. coli and B. subtilis to the treatment with ciprofloxacin-neomycin hybrid in comparison to that of each drug separately or their 1: 1 mixture.