7-(4-tetradecanoylpiperazin-1-yl)-1-cyclopropyl-6-fluoro-1,4-dihydro-4-oxoquinoline-3-carboxylic acid | 1186385-04-5

• 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-tetradecanoylpiperazin-1-yl)-1-cyclopropyl-6-fluoro-1,4-dihydro-4-oxoquinoline-3-carboxylic acid
• 英文别名: 1-Cyclopropyl-6-fluoro-4-oxo-7-(4-tetradecanoylpiperazin-1-yl)quinoline-3-carboxylic acid
• CAS: 1186385-04-5
• 化学式: C₃₁H₄₄FN₃O₄
• 分子量: 541.706
• InChiKey: YVVRAYSPANRTMS-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.4
• 重原子数：
  39
• 可旋转键数：
  15
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.65
• 拓扑面积：
  81.2
• 氢给体数：
  1
• 氢受体数：
  7

反应信息

• 作为产物：
  描述：

  环丙沙星 、 肉豆蔻酰氯 在 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 1.5h， 以65%的产率得到7-(4-tetradecanoylpiperazin-1-yl)-1-cyclopropyl-6-fluoro-1,4-dihydro-4-oxoquinoline-3-carboxylic acid
  参考文献：
  名称：

  7-((4-Substituted)piperazin-1-yl) derivatives of ciprofloxacin: Synthesis and in vitro biological evaluation as potential antitumor agents

  摘要：

  Ciprofloxacin (CP), an antibiotic has been shown to have antiproliferative and apoptotic activities in several cancer cell lines. Moreover, several reports have highlighted the interest of increasing the lipophilicity to improve the antitumor efficacy. These studies have led us to synthesize new CP derivatives of various lipophilicities and to evaluate their activity in five human cancer cell lines. With an easy and cost-efficient procedure, 31 7-((4-substituted)piperazin-1-yl) derivatives of CP were prepared that displayed IC50 values ranging from mu M to mM concentrations and are non-toxic in vivo in healthy mice as shown by their maximal tolerated dose (MTD) indices >80 mg/kg. Several derivatives displayed higher in vitro antitumor activity than parent CP however this was not dependent on the lipophilicity of the substituent. Among all synthesized derivatives, the most potent were 2 and 6h whose IC50 values were <= 10 mu M in three (derivative 2) or four (derivative 6h) cancer cell lines. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2009.06.053

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.
• 7-((4-Substituted)piperazin-1-yl) derivatives of ciprofloxacin: Synthesis and in vitro biological evaluation as potential antitumor agents
  作者：Joëlle Azéma、Brigitte Guidetti、Janique Dewelle、Benjamin Le Calve、Tatjana Mijatovic、Alexander Korolyov、Julie Vaysse、Myriam Malet-Martino、Robert Martino、Robert Kiss

  DOI：10.1016/j.bmc.2009.06.053

  日期：2009.8

  Ciprofloxacin (CP), an antibiotic has been shown to have antiproliferative and apoptotic activities in several cancer cell lines. Moreover, several reports have highlighted the interest of increasing the lipophilicity to improve the antitumor efficacy. These studies have led us to synthesize new CP derivatives of various lipophilicities and to evaluate their activity in five human cancer cell lines. With an easy and cost-efficient procedure, 31 7-((4-substituted)piperazin-1-yl) derivatives of CP were prepared that displayed IC50 values ranging from mu M to mM concentrations and are non-toxic in vivo in healthy mice as shown by their maximal tolerated dose (MTD) indices >80 mg/kg. Several derivatives displayed higher in vitro antitumor activity than parent CP however this was not dependent on the lipophilicity of the substituent. Among all synthesized derivatives, the most potent were 2 and 6h whose IC50 values were <= 10 mu M in three (derivative 2) or four (derivative 6h) cancer cell lines. (C) 2009 Elsevier Ltd. All rights reserved.