ciprofloxacin | 1446326-18-6

• 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: ciprofloxacin
• 英文别名: 1-Cyclopropyl-7-[4-(diphenylphosphanylmethyl)piperazin-1-yl]-6-fluoro-4-oxoquinoline-3-carboxylic acid；1-cyclopropyl-7-[4-(diphenylphosphanylmethyl)piperazin-1-yl]-6-fluoro-4-oxoquinoline-3-carboxylic acid
• CAS: 1446326-18-6
• 化学式: C₃₀H₂₉FN₃O₃P
• 分子量: 529.551
• InChiKey: JGDDCVANRGOERR-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  38
• 可旋转键数：
  7
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.27
• 拓扑面积：
  64.1
• 氢给体数：
  1
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  ciprofloxacin 在 selenium 作用下， 以 氯仿 为溶剂， 反应 3.0h， 以86%的产率得到1-Cyclopropyl-7-[4-(diphenylphosphinoselenoylmethyl)piperazin-1-yl]-6-fluoro-4-oxoquinoline-3-carboxylic acid
  参考文献：
  名称：

  Phosphine derivatives of ciprofloxacin and norfloxacin, a new class of potential therapeutic agents

  摘要：

  本文介绍了从环丙沙星（PPh2CH2Cp）中提取的二苯基甲基氨基膦和从诺氟沙星（PPh2CH2Nr）中提取的一种新的膦的新系列卤化物。合成的化合物通过核磁共振、质谱和 X 射线技术进行了表征。这两种膦都对以下细菌具有抗菌活性金黄色葡萄球菌、大肠杆菌、肺炎双球菌和绿脓杆菌的抗菌活性，与环丙沙星和诺氟沙星相似。它们能在相对较低的浓度下抑制微生物的生长。与膦类和未改性抗生素相比，查耳酮的活性略低。所有衍生物还作为抗癌剂对小鼠结肠癌（CT26）和人类肺腺癌（A549）进行了体外测试。细胞毒性研究表明，膦及其铬化物能够在相对较低的浓度下抑制细胞的增殖。此外，与顺铂--抗肿瘤药物的主要代表--相比，所有受测化合物对受测细胞株的活性都更强。

  DOI：

  10.1039/c3nj01243c
• 作为产物：
  描述：

  环丙沙星 、 (二苯基膦基)甲醇 在 三乙胺 作用下， 以 甲醇 、 水 为溶剂， 反应 1.0h， 生成 ciprofloxacin
  参考文献：
  名称：

  Synthesis, properties and biological activity of a novel phosphines ligand derived from ciprofloxacin

  摘要：

  Novel potential antibacterial agents derived from ciprofloxacin (HCp) were synthesized in the reaction of this antibiotic with hydroxymethyldiphenylphosphine. Detailed analysis by the NMR, IR and MS techniques attested to the identity and structure of the obtained compounds. In addition, the structure of phosphine PPh2CH2-Cp was unambiguously confirmed by X-ray crystal structural analysis. PPh2CH2-Cp exhibited an antibacterial activity comparable to that of the original drug. Cytotoxicity studies revealed that this compound was characterized by lower toxicity against mammalian cells than HCp. Besides, it did not induce a morphological change in cells after its action and was unable to degrade plasmid DNA, as well as parent antibiotic. Our results open up new possibilities in designing novel, less toxic and comparably effective antibiotics drugs. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.poly.2013.04.059

文献信息

• Polymeric micelle-mediated delivery of half-sandwich ruthenium(II) complexes with phosphanes derived from fluoroloquinolones for lung adenocarcinoma treatment
  作者：Przemysław Kołoczek、Agnieszka Skórska-Stania、Agnieszka Cierniak、Victor Sebastian、Urszula K. Komarnicka、Michał Płotek、Agnieszka Kyzioł

  DOI：10.1016/j.ejpb.2018.04.016

  日期：2018.7

  Novel half-sandwich ruthenium(II) complexes with aminomethyl(diphenyl)phosphine derived from fluoroloquinolones (RuPCp, RuPSf, RuPLm, RuPNr) were being investigated as alternatives to well-established metal-based chemotherapeutics. All compounds were characterized by elemental analysis, selected spectroscopic methods (i.e., absorption and fluorescence spectroscopies, ESI-MS, NMR, circular dichroizm)

  正在研究新型半三明治钌（II）与衍生自氟喹诺酮类化合物（RuPCp，RuPSf，RuPLm，RuPNr）的氨基甲基（二苯基）膦的配合物，以替代已建立的基于金属的化学疗法。所有化合物均通过元素分析，选定的光谱方法（即吸收光谱和荧光光谱，ESI-MS，NMR，圆二色谱），X射线衍射仪，ICP-MS和电化学技术进行表征。为了克服低溶解度，与钌配合物的全身细胞毒性有关的严重副作用并获得癌细胞的抗性，制备并表征了基于负载有选择的Ru（II）配合物的Pluronic P-123胶束的聚合物纳米制剂。产生的胶束（RuPCp_M，通过共聚焦显微镜和ICP-MS分析证明，RuPNr_M）使人肺腺癌（A549肿瘤细胞系）内的药物有效积累，从而具有细胞毒性作用。研究的复合物在体外表现出有希望的细胞毒性，IC50值显着低于参考药物顺铂。荧光光谱数据（CT-DNA滴定，体外细胞染色）以及DNA片段分析（pBR322
• Coordination versatility of phosphine derivatives of fluoroquinolones. New Cu^I and Cu^II complexes and their interactions with DNA
  作者：A. Bykowska、R. Starosta、J. Jezierska、M. Jeżowska-Bojczuk

  DOI：10.1039/c5ra07483e

  日期：——

  and IR spectroscopies. X-ray techniques were used to determine the crystal and molecular structures of [CuI-PCp]·CH2Cl2·CH3CN and OPCp-CuII]NO3·3H2O. For all the studied compounds, the ability to interact with DNA was determined using three different methods. The results of gel electrophoresis revealed that in the presence or absence of H2O2, the copper(I) complexes caused only single-stranded cleavage

  在本文中，提出了新的铜（I）和铜（II）与两种氟喹诺酮（环丙沙星和诺氟沙星）的膦衍生物的配合物。合成的化合物（[Cu I -PCp]，[Cu I -PNr]，[OPCp-Cu II ] +和[OPNr-Cu II ] +）通过元素分析和质谱以及NMR，EPR和MS进行表征。红外光谱。用X射线技术测定了[Cu I -PCp]·CH 2 Cl 2 ·CH 3 CN和OPCp-Cu II ] NO 3 ·3H 2的晶体和分子结构。O.对于所有研究的化合物，使用三种不同的方法确定了与DNA相互作用的能力。凝胶电泳的结果表明，在存在或不存在H 2 O 2的情况下，铜（I）配合物仅引起DNA的糖-磷酸骨架的单链裂解。反过来，铜（II）配合物仅在氧化剂存在下损坏质粒。H 2 O 2的添加导致质粒结构发生明显变化，导致其天然形式完全消失。检测到由单链和双链裂解产生的II型和III型。在存在溴化乙锭（EB）
• Synthesis, properties and biological activity of a novel phosphines ligand derived from ciprofloxacin
  作者：Aleksandra Bykowska、Radosław Starosta、Anna Brzuszkiewicz、Barbara Bażanów、Magdalena Florek、Natalia Jackulak、Jarosław Król、Jakub Grzesiak、Krzysztof Kaliński、Małgorzata Jeżowska-Bojczuk

  DOI：10.1016/j.poly.2013.04.059

  日期：2013.8

  Novel potential antibacterial agents derived from ciprofloxacin (HCp) were synthesized in the reaction of this antibiotic with hydroxymethyldiphenylphosphine. Detailed analysis by the NMR, IR and MS techniques attested to the identity and structure of the obtained compounds. In addition, the structure of phosphine PPh2CH2-Cp was unambiguously confirmed by X-ray crystal structural analysis. PPh2CH2-Cp exhibited an antibacterial activity comparable to that of the original drug. Cytotoxicity studies revealed that this compound was characterized by lower toxicity against mammalian cells than HCp. Besides, it did not induce a morphological change in cells after its action and was unable to degrade plasmid DNA, as well as parent antibiotic. Our results open up new possibilities in designing novel, less toxic and comparably effective antibiotics drugs. (C) 2013 Elsevier Ltd. All rights reserved.
• Phosphine derivatives of ciprofloxacin and norfloxacin, a new class of potential therapeutic agents
  作者：Aleksandra Bykowska、Radosław Starosta、Urszula K. Komarnicka、Zbigniew Ciunik、Agnieszka Kyzioł、Katarzyna Guz-Regner、Gabriela Bugla-Płoskońska、Małgorzata Jeżowska-Bojczuk

  DOI：10.1039/c3nj01243c

  日期：——

  In this paper a new series of chalcogenides of diphenylmethylaminophosphine derived from ciprofloxacin (PPh2CH2Cp) and a new phosphine derived from norfloxacin (PPh2CH2Nr) are presented. The synthesized compounds were characterized by NMR, MS and X-ray techniques. Both phosphines exhibit antibacterial activity against: S. aureus, E. coli, K. pneumoniae and P. aeruginosa, similar to ciprofloxacin and norfloxacin. They inhibit the growth of microorganisms in relatively low concentrations. Chalcogenides are slightly less active than phosphines and unmodified antibiotics. All the derivatives were also tested in vitro as anticancer agents towards mouse colon carcinoma (CT26) and human lung adenocarcinoma (A549). Cytotoxicity studies revealed that phosphines and their chalcogenides are able to inhibit the proliferation of the cells at relatively low concentrations. Moreover, all the tested compounds are more active against tested cell lines than cisplatin – the main representative of antitumor drugs.

  本文介绍了从环丙沙星（PPh2CH2Cp）中提取的二苯基甲基氨基膦和从诺氟沙星（PPh2CH2Nr）中提取的一种新的膦的新系列卤化物。合成的化合物通过核磁共振、质谱和 X 射线技术进行了表征。这两种膦都对以下细菌具有抗菌活性金黄色葡萄球菌、大肠杆菌、肺炎双球菌和绿脓杆菌的抗菌活性，与环丙沙星和诺氟沙星相似。它们能在相对较低的浓度下抑制微生物的生长。与膦类和未改性抗生素相比，查耳酮的活性略低。所有衍生物还作为抗癌剂对小鼠结肠癌（CT26）和人类肺腺癌（A549）进行了体外测试。细胞毒性研究表明，膦及其铬化物能够在相对较低的浓度下抑制细胞的增殖。此外，与顺铂--抗肿瘤药物的主要代表--相比，所有受测化合物对受测细胞株的活性都更强。