Studies on 6-Aminoquinolones:  Synthesis and Antibacterial Evaluation of 6-Amino-8-methylquinolones

Cecchetti, Violetta; Fravolini, Arnaldo; Lorenzini, Maria Cristina; Tabarrini, Oriana; Terni, Patrizia; Tao, Xin

doi:10.1021/jm950558v

Cited by 69 publications

(45 citation statements)

References 15 publications

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“…For the 6-amino compounds as well, the overall potency is highly dependent on substituents at positions C-7 and C-8. Similar to the fluoroquinolones, a methyl (and probably a methoxy), at position 8 enhances Gram-positive activity, at least in vitro [40].…”

Section: Positionmentioning

confidence: 99%

“…Another group of agents with novel substituents at C-6 position are the 6-nitro and 6-amino quinolones, which have expanded activity against Gram-positive cocci [39,40]. For the 6-amino compounds as well, the overall potency is highly dependent on substituents at positions C-7 and C-8.…”

Section: Positionmentioning

confidence: 99%

“…Manipulation of the group at position 8 has also been shown to play a role in altering oral pharmacokinetics, broadening the spectrum of activity and reducing the selection of mutants [40,[67][68][69]. Halogen substituents, as well as a methyl or methoxy also increase the in vitro activity against Gram-positive cocci, even in those bacteria resistant to older fluoroquinolones.…”

Section: Positionmentioning

confidence: 99%

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Structural Features of New Quinolones and Relationship to Antibacterial Activity Against Gram-positive Bacteria

Emami¹,

Shafiee²,

Foroumadi

2006

MRMC

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A major recent focus of quinolone antibacterials has been the development of agents with enhanced activity against Gram-positive bacteria. The extensive research efforts have enabled a better definition of the structural features of quinolones that offer the best combination of clinical efficacy and reduced resistance selection in Gram-positive bacteria. This review considers the structural features of new quinolones and relationship to antibacterial activity against Gram-positive bacteria, while trying to position them in the context of recent and possible future advances based on an understanding of their chemical structure and how these impact on target specificity, avoidance of efflux and prevention of emergence of quinolone-resistant mutants in Gram-positive bacteria.

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Section: Positionmentioning

confidence: 99%

Section: Positionmentioning

confidence: 99%

Section: Positionmentioning

confidence: 99%

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Structural Features of New Quinolones and Relationship to Antibacterial Activity Against Gram-positive Bacteria

Emami¹,

Shafiee²,

Foroumadi

2006

MRMC

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“…Among them, compound 2 (Fig. ) with N‐1 cyclopropyl exhibited high in vitro (MIC: 0.008–0.06 μg/mL against most of the tested Gram‐negative and Gram‐positive organisms) and in vivo potency and could act as a lead for further exploitation . Asanhina et al .…”

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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“…Thus, recent efforts have been directed toward the synthesis of new quinolones that can provide improved Gram-positive antibacterial activity, while retaining the good Gram-negative activity of early fluoroquinolones, such as ciprofloxacin (CPFX) and ofloxacin [5][6][7][8].…”

Section: Introductionmentioning

confidence: 99%

Synthesis and In Vitro Antibacterial Activity of 7‐(3‐Alkoxyimino‐4‐methyl‐4‐methylaminopiperidin‐1‐yl)‐fluoroquinolone Derivatives

Zhang

Feng

You

et al. 2010

Archiv der Pharmazie

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A series of novel 7-(3-alkoxyimino-4-methyl-4-methylaminopiperidin-1-yl)fluoroquinolone derivatives were designed, synthesized, and characterized by 1H-NMR, MS, and HRMS. These fluoroquinolones were evaluated for their in-vitro antibacterial activity against representative Gram-positive and Gram-negative strains. Generally, all of the target compounds have considerable antibacterial activity against the tested forty strains, and exhibit exceptional potency in inhibiting the growth of methicillin-sensitive Staphylococcus aureus (MSSA) and methicillin-resistant S. aureus (MRSA) ATCC33591 (MICs: 0.06 to 2 microg/mL). In particular, compounds 14, 19, 28, and 29 are fourfold more potent than ciprofloxacin against MSSA 08-49. Compounds 23, 26, and 27 are twofold more potent than ciprofloxacin against MRSA ATCC33591 and MSSA ATCC29213. In addition, compound 14 exhibits excellent activity (MIC: 0.06 microg/mL) against Acinetobactes calcoaceticus, which is two- to 16-fold more potent than the reference drugs gemifloxacin, levofloxacin, and ciprofloxacin.

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Studies on 6-Aminoquinolones: Synthesis and Antibacterial Evaluation of 6-Amino-8-methylquinolones

Cited by 69 publications

References 15 publications

Structural Features of New Quinolones and Relationship to Antibacterial Activity Against Gram-positive Bacteria

Structural Features of New Quinolones and Relationship to Antibacterial Activity Against Gram-positive Bacteria

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

Synthesis and In Vitro Antibacterial Activity of 7‐(3‐Alkoxyimino‐4‐methyl‐4‐methylaminopiperidin‐1‐yl)‐fluoroquinolone Derivatives

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