1-cyclopropyl-6-fluoro-7-(4-hexanoylpiperazin-1-yl)-4-oxo-1,4-dihydroquinoline-3-carboxylic acid | 151602-46-9

• 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-cyclopropyl-6-fluoro-7-(4-hexanoylpiperazin-1-yl)-4-oxo-1,4-dihydroquinoline-3-carboxylic acid
• 英文别名: 1-Cyclopropyl-6-fluoro-7-(4-hexanoylpiperazin-1-yl)-4-oxoquinoline-3-carboxylic acid
• CAS: 151602-46-9
• 化学式: C₂₃H₂₈FN₃O₄
• 分子量: 429.491
• InChiKey: ZTJSHYXWNHFZLK-UHFFFAOYSA-N

物化性质

• 沸点：
  663.5±55.0 °C(Predicted)
• 密度：
  1.346±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  31
• 可旋转键数：
  7
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.52
• 拓扑面积：
  81.2
• 氢给体数：
  1
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  1-cyclopropyl-6-fluoro-7-(4-hexanoylpiperazin-1-yl)-4-oxo-1,4-dihydroquinoline-3-carboxylic acid 、 (3R,4S)-1-butan-2-ylsulfanyl-3-hydroxy-4-phenylazetidin-2-one 在 4-二甲氨基吡啶 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 作用下， 以 二氯甲烷 为溶剂， 反应 24.0h， 生成
  参考文献：
  名称：

  Antibiotic compositions and methods of use

  摘要：

  本公开的实施例提供了包含含有N-硫代β-内酰胺基团的抗生素的组合物、包括该抗生素的药物组合物、治疗疾病（例如细菌感染）的方法、使用组合物或药物组合物的治疗方法等。

  公开号：

  US09670179B1
• 作为产物：
  描述：

  环丙沙星 、 己酰氯 在 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 0.25h， 生成 1-cyclopropyl-6-fluoro-7-(4-hexanoylpiperazin-1-yl)-4-oxo-1,4-dihydroquinoline-3-carboxylic acid
  参考文献：
  名称：

  Studies on the antimicrobial properties of N-acylated ciprofloxacins

  摘要：

  Fluoroquinolone antibiotics have been a mainstay in the treatment of bacterial diseases. The most notable representative, ciprofloxacin, possesses potent antimicrobial activity; however, a rise in resistance to this agent necessitates development of novel derivatives to prolong the clinical lifespan of these antibiotics. Herein we have synthesized and analyzed the antimicrobial properties of a library of N-acylated ciprofloxacin analogues. We find that these compounds are broadly effective against Gram-positive and Gram-negative bacteria, with many proving more effective than the parental drug, and several possessing MICs <= 1.0 mu g/ml against methicillin-resistant Staphylococcus aureus and Bartonella species. An analysis of spontaneous mutation frequencies reveals very low potential for resistance in MRSA compared to existing fluoroquinolones. Mode of action profiling reveals that modification of the piperazinyl nitrogen by acylation does not alter the effect of these molecules towards their bacterial target. We also present evidence that these N-acylated compounds are highly effective at killing intracellular bacteria, suggesting the suitability of these antibiotics for therapeutic treatment. (c) 2012 Published by Elsevier

  DOI：

  10.1016/j.bmcl.2012.05.026

文献信息

• Fluoroquinolones and use thereof to treat bacterial infections
  申请人：UNIVERSITÉ PIERRE ET MARIE CURIE—PARIS 6 (UPMC)

  公开号：US10087165B2

  公开（公告）日：2018-10-02

  The present invention relates to novel fluoroquinolones, pharmaceutical compositions or medicament containing them and use thereof to treat bacterial infection.

  本发明涉及新型氟喹诺酮类药物、药物组合物或含有它们的药物以及使用它们治疗细菌感染。
• NOVEL FLUOROQUINOLONES AND USE THEREOF TO TREAT BACTERIAL INFECTIONS
  申请人：Université Pierre et Marie Curie - Paris 6 (UPMC)

  公开号：EP3157911A1

  公开（公告）日：2017-04-26
• [EN] NOVEL FLUOROQUINOLONES AND USE THEREOF TO TREAT BACTERIAL INFECTIONS<br/>[FR] NOUVEAUX FLUOROQUINOLONES ET LEUR UTILISATION POUR TRAITER DES INFECTIONS BACTÉRIENNES
  申请人：UNIVERSITÉ PIERRE ET MARIE CURIE PARIS 6 UPMC

  公开号：WO2015193454A1

  公开（公告）日：2015-12-23

  The present invention relates to novel fluoroquinolones, pharmaceutical compositions or medicament containing them and use thereof to treat bacterial infection.
• Studies on the antimicrobial properties of N-acylated ciprofloxacins
  作者：Ryan Cormier、Whittney N. Burda、Lacey Harrington、Jordan Edlinger、Karthik M. Kodigepalli、John Thomas、Rebecca Kapolka、Glen Roma、Burt E. Anderson、Edward Turos、Lindsey N. Shaw

  DOI：10.1016/j.bmcl.2012.05.026

  日期：2012.10

  Fluoroquinolone antibiotics have been a mainstay in the treatment of bacterial diseases. The most notable representative, ciprofloxacin, possesses potent antimicrobial activity; however, a rise in resistance to this agent necessitates development of novel derivatives to prolong the clinical lifespan of these antibiotics. Herein we have synthesized and analyzed the antimicrobial properties of a library of N-acylated ciprofloxacin analogues. We find that these compounds are broadly effective against Gram-positive and Gram-negative bacteria, with many proving more effective than the parental drug, and several possessing MICs <= 1.0 mu g/ml against methicillin-resistant Staphylococcus aureus and Bartonella species. An analysis of spontaneous mutation frequencies reveals very low potential for resistance in MRSA compared to existing fluoroquinolones. Mode of action profiling reveals that modification of the piperazinyl nitrogen by acylation does not alter the effect of these molecules towards their bacterial target. We also present evidence that these N-acylated compounds are highly effective at killing intracellular bacteria, suggesting the suitability of these antibiotics for therapeutic treatment. (c) 2012 Published by Elsevier
• Antibiotic compositions and methods of use
  申请人：Turos Edward

  公开号：US09670179B1

  公开（公告）日：2017-06-06

  Embodiments of the present disclosure provide for compositions including an antibiotic containing a N-thiolated beta-lactam moiety, pharmaceutical compositions including the antibiotic, methods of treatment of a condition (e.g., bacterial infection), methods of treatment using compositions or pharmaceutical compositions, and the like.

  本公开的实施例提供了包含含有N-硫代β-内酰胺基团的抗生素的组合物、包括该抗生素的药物组合物、治疗疾病（例如细菌感染）的方法、使用组合物或药物组合物的治疗方法等。