Design, Synthesis and Antibacterial Evaluation of 1‐[(1R,2S)‐2‐Fluorocyclopropyl]ciprofloxacin‐1,2,4‐triazole‐5(4H)‐thione Hybrids

Gao, Yang; Na, Lu-Xin; Xu, Zhi; Zhang, Shu; Wang, Apeng; Lü, Kai; Guo, Hai‐Ming; Liu, Mingliang

doi:10.1002/cbdv.201800261

Cited by 25 publications

(12 citation statements)

References 22 publications

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“…As reported, norfloxacin was used as a positive control in the pipeline publications, including norfloxacin derivatives synthesis. Norfloxacin MIC against Gram-positive is presented in Table 3 [ 1 , 23 , 24 , 26 , 28 , 34 , 35 , 36 , 37 , 38 , 39 , 40 , 41 , 42 , 43 , 44 , 45 , 46 , 47 , 48 , 49 , 50 , 51 , 52 , 53 , 54 , 55 , 56 , 57 , 58 , 59 , 60 , 61 , 62 , 63 , 64 , 65 , 66 , 67 , 68 , 69 , 70 , 71 ]. In brief, norfloxacin inhibitory activity against a panel of Gram-positive bacteria regardless of the strain varied relatively.…”

Section: Fq’s Antibacterial Biological Activitymentioning

confidence: 99%

“…Considering the third FQ reference, levofloxacin was adopted by many researchers’ as a reference control, and exhibited variable antimicrobial activity against E. faecalis (MIC ranged from 1.384 µM for E. faecalis 51575 [ 55 ], 177.220 µM for E. faecalis ATCC 700221 [ 51 ]) as an example. A notable difference in levofloxacin potency against different staph strains, including methicillin-sensitive S. aureus (MSSA) [ 26 , 53 , 54 , 68 , 69 ], methicillin-resistant S. aureus (MRSA) [ 26 , 53 , 54 , 68 , 69 ], S. epidermidis , and S. pneumoniae was observed ( Table 3 ).…”

Section: Fq’s Antibacterial Biological Activitymentioning

confidence: 99%

“…Following scientific reports in the literature, levofloxacin exhibited superior antibacterial activity against Gram-positive S. epidermis strains [ 51 , 55 , 63 ] and moxifloxacin is generally the most potent amongst FQs a, gainst Gram-positive and negative bacteria [ 26 ]. Moxifloxacin was the latent agent against the food poisoning pathogen L. monocytogenes ATCC 43251 (MIC < 1.370 µM [ 28 ]) when compared with other FQs as ciprofloxacin (MIC 3.954 µM−12.072 [ 28 , 64 ]) and norfloxacin (MIC < 8.267 µM [ 28 ]).…”

Section: Fq’s Antibacterial Biological Activitymentioning

confidence: 99%

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Fluoroquinolones’ Biological Activities against Laboratory Microbes and Cancer Cell Lines

2022

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Development of novel derivatives to rein in and fight bacteria have never been more demanding, as microbial resistance strains are alarmingly increasing. A multitude of new fluoroquinolones derivatives with an improved spectrum of activity and/or enhanced pharmacokinetics parameters have been widely explored. Reporting novel antimicrobial agents entails comparing their potential activity to their parent drugs; hence, parent fluoroquinolones have been used in research as positive controls. Given that these fluoroquinolones possess variable activities according to their generation, it is necessary to include parent compounds and market available antibiotics of the same class when investigating antimicrobial activity. Herein, we provide a detailed guide on the in vitro biological activity of fluoroquinolones based on experimental results published in the last years. This work permits researchers to compare and analyze potential fluoroquinolones as positive control agents and to evaluate changes occurring in their activities. More importantly, the selection of fluoroquinolones as positive controls by medicinal chemists when investigating novel FQs analogs must be correlated to the laboratory pathogen inquest for reliable results.

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Section: Fq’s Antibacterial Biological Activitymentioning

confidence: 99%

Section: Fq’s Antibacterial Biological Activitymentioning

confidence: 99%

Section: Fq’s Antibacterial Biological Activitymentioning

confidence: 99%

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Fluoroquinolones’ Biological Activities against Laboratory Microbes and Cancer Cell Lines

2022

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“…Hydrolysis of disubstituted hydrazinecarbothioamides 130b – d with aqueous sodium hydroxide gave 1,2,4-triazole-5-thiones 92b – d . Mannich reaction of 1,2,4-triazole-5-thiones 92b – d , 1-[(1 R ,2 S )-2-fluorocyclopropyl]CPFX ( 133 ) and formaldehyde afforded 1-[(1 R ,2 S )-2-fluorocyclopropyl]CPFX-1,2,4-triazole-5-thiones 134a – c in 52–57% yields ( Scheme 35 ) [ 67 ].…”

Section: Synthesis Of 124-triazole-3-thionesmentioning

confidence: 99%

“…Antibacterial activity against different pathogens showed that all of the CPFX-1,2,4-triazole-5-thiones 134a – c were more potent than the parent 1-[(1 R ,2 S )-2-fluorocyclopropyl]-CPFX 133 and comparable to ciprofloxacin and levofloxacin against the majority of the tested pathogens. Moreover, the anti-Gram negative bacterial activity of 134a – c was far more potent than the reference named Vancomycin (VAN) [ 67 ].…”

Section: Synthesis Of 124-triazole-3-thionesmentioning

confidence: 99%

Chemistry and Biological Activities of 1,2,4-Triazolethiones—Antiviral and Anti-Infective Drugs

et al. 2020

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Mercapto-substituted 1,2,4-triazoles are very interesting compounds as they play an important role in chemopreventive and chemotherapeutic effects on cancer. In recent decades, literature has been enriched with sulfur- and nitrogen-containing heterocycles which are used as a basic nucleus of different heterocyclic compounds with various biological applications in medicine and also occupy a huge part of natural products. Therefore, we shed, herein, more light on the synthesis of this interesting class and its application as a biologically active moiety. They might also be suitable as antiviral and anti-infective drugs.

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1,2,4‐Triazole hybrids with potential antibacterial activity against methicillin‐resistant Staphylococcus aureus

2020

Archiv der Pharmazie

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Methicillin‐resistant Staphylococcus aureus (MRSA) has developed numerous mechanisms of virulence and strategies to evade the human immune system, and it can be transmitted between humans, animals, and the environment. Thus, MRSA is an important cause of morbidity and mortality in both hospitals and in the community, creating an urgent demand for the development of novel anti‐MRSA candidates. The 1,2,4‐triazole nucleus is a bioisostere of amide, ester, and carboxylic acid, and the 1,2,4‐triazole ring is found in many compounds with diverse biological effects. 1,2,4‐Triazole derivatives could exert their antibacterial activity through inhibition of efflux pumps, filamentous temperature‐sensitive protein Z, penicillin‐binding protein, DNA gyrase, and topoisomerase IV, and they play an important role in the discovery of novel antibacterial agents. Among them, 1,2,4‐triazole hybrids, which have the potential to exert dual/multiple mechanisms of action, possess a promising broad‐spectrum antibacterial activity against a panel of clinically important drug‐resistant pathogens including MRSA. This review outlines the recent developments of 1,2,4‐triazole hybrids with a potential anti‐MRSA activity, covering articles published between 2010 and 2020. The mechanisms of action, critical aspects of their design, and structure–activity relationships are also discussed.

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Design, Synthesis and Antibacterial Evaluation of 1‐[(1R,2S)‐2‐Fluorocyclopropyl]ciprofloxacin‐1,2,4‐triazole‐5(4H)‐thione Hybrids

Cited by 25 publications

References 22 publications

Fluoroquinolones’ Biological Activities against Laboratory Microbes and Cancer Cell Lines

Fluoroquinolones’ Biological Activities against Laboratory Microbes and Cancer Cell Lines

Chemistry and Biological Activities of 1,2,4-Triazolethiones—Antiviral and Anti-Infective Drugs

1,2,4‐Triazole hybrids with potential antibacterial activity against methicillin‐resistant Staphylococcus aureus

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