Synthesis and Antibacterial Activity of Amino Acid and Dipeptide Prodrugs of IMB-070593, a Fluoroquinolone Candidate

Zhang, Tingting; Wu, Jinwei; Chen, Shihong; Liu, Kaixiang; Lin, Yabin; Guo, Hai‐Ming; Liu, Mingliang

doi:10.3390/molecules19056822

Cited by 12 publications

(13 citation statements)

References 19 publications

(18 reference statements)

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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%

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%

Fluoroquinolones’ Biological Activities against Laboratory Microbes and Cancer Cell Lines

2022

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“…Based on that, various fluoroquinolones 12 (Fig. ) with different oximes at C‐7 position were screened for their antibacterial , antitumor , and anti‐TB activities by our group. The preliminary results indicated that the side chains at C‐7 position have great influence on their biological activities, and the anti‐TB SAR revealed that (1) piperidine > pyrrolidine > azetidine; (2) small –H was more favorable than large –Me at R 2 position, which may be attributed to the steric hindrance; (3) for the fluoroquinolone moieties, C‐OMe ≈ CH ≥ N. Among them, the oxime‐functionalized piperidinyl‐based fluoroquinolone IMB‐070593 displayed excellent antibacterial and anti‐TB activities as well as extremely low phototoxicity, hepatotoxicity, and cardiac toxicity .…”

Section: Quinolone‐based Derivativesmentioning

confidence: 99%

Quinoline Derivatives with Potential Activity Against Multidrug‐resistant Tuberculosis

Zhou

et al. 2018

Journal of Heterocyclic Chem

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Tuberculosis (TB), which affects primarily the lungs (pulmonary TB) apart from other vital organs, is a life‐threatening chronic deadliest infectious disease caused by members of Mycobacterium tuberculosis (MTB) complex and mainly by MTB itself. The emergence of MTB new virulent forms that are resistant to some or all first‐line and second‐line anti‐TB agents, including multidrug‐resistant (MDR), extensively drug‐resistant, and totally drug‐resistant strains has further aggravated the spread of this disease and was increased up to an alarming level in the recent decades. More than ever, it is imperative to develop novel, high effective, and fast acting anti‐TB drugs to prevent the spread of TB, particularly in its hard‐to‐kill MDR‐TB, extensively drug‐resistant‐TB, and totally drug‐resistant‐TB strains. In recent years, numerous compounds have been synthesized for this purpose, but only a handful of compounds have entered human trials after the discovery of rifampicin, reflecting the inherent difficulties of developing new anti‐TB agents. Despite of bedaquiline and delamanid have received approval from many countries for treatment of MDR‐TB infected patients, both drugs are associated with serious side effects and are only recommended for those MDR‐TB patients without other treatment options. All these aforementioned facts make it an urgent need to develop novel drugs. Quinoline‐based derivatives including quinolones ex biological activities, and some of them displayed excellent in vitro and in vivo activities against MDR‐TB. This review outlines the recent developments of quinoline‐based derivatives with potential activity against MDR‐TB as well as the structure–activity relationship.

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“…Quinolones with oxime‐functionalized azetidines, pyrrolidines, or piperidines have caused great interests since the discovery of the fourth generation FQs GMFX and its derivatives zabofloxacin as well as DW286, which exhibit excellent in vitro and in vivo activities against both Gram‐positive and Gram‐negative organisms including quinolone‐resistant pathogens and improved pharmacokinetic profiles . Some of them were found to have considerable activities against Gram‐negative bacteria, but few of them were superior to GMFX.…”

Section: Structure–activity Relationshipmentioning

confidence: 99%

4‐Quinolone Derivatives and Their Activities Against Gram‐negative Pathogens

Jiang

2018

Journal of Heterocyclic Chem

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Gram‐negative pathogens represent a significant global health threat, while the emergency and widespread of drug resistance make the situation even worse. As “privileged building blocks,” 4‐quinolones including fluoroquinolones are mainstays of chemotherapy against various bacterial infections. However, as other antibiotics, the resistance of Gram‐negative bacteria to 4‐quinolones develops rapidly and spreads widely throughout the world. To overcome the resistance and improve the potency, a number of 4‐quinolone derivatives were designed, synthesized, and screened for their in vitro and in vivo activities against representative Gram‐negative pathogens. This review aims to summarize the recent advances made towards the discovery of 4‐quinolone derivatives as anti‐Gram‐negative agents as well as their structure–activity relationship. The enriched structure–activity relationship paves the way to the further rational development of 4‐quinolones with excellent potency against both drug‐susceptible and drug‐resistant Gram‐negative pathogens.

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Synthesis and Antibacterial Activity of Amino Acid and Dipeptide Prodrugs of IMB-070593, a Fluoroquinolone Candidate

Cited by 12 publications

References 19 publications

Fluoroquinolones’ Biological Activities against Laboratory Microbes and Cancer Cell Lines

Fluoroquinolones’ Biological Activities against Laboratory Microbes and Cancer Cell Lines

Quinoline Derivatives with Potential Activity Against Multidrug‐resistant Tuberculosis

4‐Quinolone Derivatives and Their Activities Against Gram‐negative Pathogens

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