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喹诺酮类和氟喹诺酮类的修饰：杂化化合物和双作用分子。

Modifications of quinolones and fluoroquinolones: hybrid compounds and dual-action molecules.

作者信息

Fedorowicz Joanna, Sączewski Jarosław

机构信息

Department of Organic Chemistry, Medical University of Gdańsk, Al. Gen. J. Hallera 107, 80-416 Gdańsk, Poland.

出版信息

Monatsh Chem. 2018;149(7):1199-1245. doi: 10.1007/s00706-018-2215-x. Epub 2018 Jun 7.

DOI:10.1007/s00706-018-2215-x
PMID:29983452
原文链接:https://pmc.ncbi.nlm.nih.gov/articles/PMC6006264/
Abstract

ABSTRACT

This review is aimed to provide extensive survey of quinolones and fluoroquinolones for a variety of applications ranging from metal complexes and nanoparticle development to hybrid conjugates with therapeutic uses. The review covers the literature from the past 10 years with emphasis placed on new applications and mechanisms of pharmacological action of quinolone derivatives. The following are considered: metal complexes, nanoparticles and nanodrugs, polymers, proteins and peptides, NO donors and analogs, anionic compounds, siderophores, phosphonates, and prodrugs with enhanced lipophilicity, phototherapeutics, fluorescent compounds, triazoles, hybrid drugs, bis-quinolones, and other modifications. This review provides a comprehensive resource, summarizing a broad range of important quinolone applications with great utility as a resource concerning both chemical modifications and also novel hybrid bifunctional therapeutic agents.

摘要

摘要

本综述旨在广泛探讨喹诺酮类和氟喹诺酮类药物在多种应用中的情况，这些应用涵盖从金属配合物、纳米颗粒开发到具有治疗用途的杂化共轭物等领域。该综述涵盖了过去10年的文献，重点关注喹诺酮衍生物的新应用和药理作用机制。内容包括：金属配合物、纳米颗粒和纳米药物、聚合物、蛋白质和肽、一氧化氮供体及类似物、阴离子化合物、铁载体、膦酸盐以及具有增强亲脂性的前药、光疗法、荧光化合物、三唑类、杂化药物、双喹诺酮类以及其他修饰。本综述提供了一个全面的资源，总结了广泛的重要喹诺酮应用，作为有关化学修饰和新型杂化双功能治疗剂的资源具有很大的实用价值。

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Antibiotics (Basel). 2024 Feb 1;13(2):142. doi: 10.3390/antibiotics13020142.
6
Menthol- and thymol-based ciprofloxacin derivatives against Mycobacterium tuberculosis: in vitro activity, lipophilicity, and computational studies.基于薄荷醇和百里酚的环丙沙星衍生物抗结核分枝杆菌：体外活性、亲脂性和计算研究。
Sci Rep. 2023 Sep 28;13(1):16328. doi: 10.1038/s41598-023-43708-4.
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Fluoroquinolone Analogs, SAR Analysis, and the Antimicrobial Evaluation of 7-Benzimidazol-1-yl-fluoroquinolone in In Vitro, In Silico, and In Vivo Models.氟喹诺酮类似物、SAR 分析以及 7-苯并咪唑-1-基-氟喹诺酮在体外、计算机模拟和体内模型中的抗菌评价。
Molecules. 2023 Aug 11;28(16):6018. doi: 10.3390/molecules28166018.
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Synthesis and Antibacterial Evaluation of Ciprofloxacin Congeners with Spirocyclic Amine Periphery.具有螺环胺外围的环丙沙星同系物的合成与抗菌评价。
Int J Mol Sci. 2023 Jan 4;24(2):954. doi: 10.3390/ijms24020954.
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Novel ciprofloxacin and norfloxacin-tetrazole hybrids as potential antibacterial and antiviral agents: Targeting topoisomerase and SARS-CoV-2-MPro.新型环丙沙星和诺氟沙星-四氮唑杂化物作为潜在的抗菌和抗病毒药物：靶向拓扑异构酶和SARS-CoV-2-MPro
J Mol Struct. 2023 Feb 15;1274:134507. doi: 10.1016/j.molstruc.2022.134507. Epub 2022 Nov 7.
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Synthesis and molecular docking of new N4-piperazinyl ciprofloxacin hybrids as antimicrobial DNA gyrase inhibitors.合成和分子对接新的 N4-哌嗪基环丙沙星杂合体作为抗菌 DNA 拓扑异构酶抑制剂。
Mol Divers. 2023 Aug;27(4):1751-1765. doi: 10.1007/s11030-022-10528-z. Epub 2022 Sep 24.
Synthesis, antibacterial properties and 2D-QSAR studies of quinolone-triazole conjugates.
喹诺酮-三唑共轭物的合成、抗菌性能及二维定量构效关系研究
Eur J Med Chem. 2018 Jan 1;143:1524-1534. doi: 10.1016/j.ejmech.2017.10.042. Epub 2017 Oct 16.
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Enhancing the Potency of Nalidixic Acid toward a Bacterial DNA Gyrase with Conjugated Peptides.通过共轭肽增强萘啶酸对细菌DNA回旋酶的效力。
ACS Chem Biol. 2017 Oct 20;12(10):2563-2569. doi: 10.1021/acschembio.7b00540. Epub 2017 Sep 1.
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Design and synthesis of theranostic antibiotic nanodrugs that display enhanced antibacterial activity and luminescence.设计和合成具有增强抗菌活性和发光的治疗性抗生素纳米药物。
Proc Natl Acad Sci U S A. 2017 Aug 8;114(32):8464-8469. doi: 10.1073/pnas.1708556114. Epub 2017 Jul 25.
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Design, synthesis and in vitro anti-mycobacterial evaluation of gatifloxacin-1H-1,2,3-triazole-isatin hybrids.加替沙星-1H-1,2,3-三唑-异吲哚酮杂合物的设计、合成及体外抗分枝杆菌活性评价
Bioorg Med Chem Lett. 2017 Aug 15;27(16):3643-3646. doi: 10.1016/j.bmcl.2017.07.023. Epub 2017 Jul 8.
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Ciprofloxacin-nitroxide hybrids with potential for biofilm control.具有生物膜控制潜力的环丙沙星-氮氧化物杂化物。
Eur J Med Chem. 2017 Sep 29;138:590-601. doi: 10.1016/j.ejmech.2017.06.058. Epub 2017 Jun 28.
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Azide-alkyne cycloaddition towards 1H-1,2,3-triazole-tethered gatifloxacin and isatin conjugates: Design, synthesis and in vitro anti-mycobacterial evaluation.叠氮-炔环加成法构建 1H-1,2,3-三氮唑键合加替沙星和色酮轭合物：设计、合成与体外抗分枝杆菌活性评价。
Eur J Med Chem. 2017 Sep 29;138:66-71. doi: 10.1016/j.ejmech.2017.05.057. Epub 2017 Jun 9.
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Synthesis and Evaluation of Antimicrobial Activity of [R₄W₄K]-Levofloxacin and [R₄W₄K]-Levofloxacin-Q Conjugates.[R₄W₄K]-左氧氟沙星及[R₄W₄K]-左氧氟沙星-Q缀合物的合成及其抗菌活性评价
Molecules. 2017 Jun 8;22(6):957. doi: 10.3390/molecules22060957.
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Design, synthesis and biological evaluation of ciprofloxacin tethered bis-1,2,3-triazole conjugates as potent antibacterial agents.设计、合成及生物评价新型环丙沙星双三唑连接物的抗菌活性。
Eur J Med Chem. 2016 Nov 29;124:218-228. doi: 10.1016/j.ejmech.2016.08.031. Epub 2016 Aug 17.