Synthesis and antibacterial properties of new N<sub>4</sub>-acetylated hexahydro-2,7-dioxopyrido[2,3-<i>f</i>]quinoxaline-8-carboxylic acids

Al‐Hiari, Yusuf; Shakya, Ashok K.; Alzweiri, Muhammed; Al-Qirim, Tariq; Shattat, Ghassan; El‐Abadelah, Mustafa M.

doi:10.3109/14756366.2010.543421

Cited by 8 publications

(2 citation statements)

References 29 publications

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“…It also facilitates nitration at the C-8. A halogen at the C-7 position allows nucleophilic aromatic substitution to submit an amino group to generate a variety of novel bioactive 7,8-bridged tricyclic quinolones, [60][61][62][63] secondary amines and tricyclic or tetracyclic quinolones.…”

Section: Discussionmentioning

confidence: 99%

Synthesis and Anticancer Activity of 1‐(Ethyl/Methyl)‐7‐(p‐Methoxybenzyl Amino) and 7‐Amino‐6‐Fluoroquinolone‐Boron Difluoride Complexes

Hernández‐López,

Tejada‐Rodríguez,

Leyva‐Ramos

et al. 2023

ChemistrySelect

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Novel 1‐(ethyl/methyl)‐7‐(p‐methoxybenzyl amino) and 7‐amino‐6‐fluoroquinolone‐boron difluoride complexes were synthesized, and their biological activity was studied, comparing the influence of the nature of 7‐substituent as well as N‐1 substituent. The quinolone compounds were characterized by IR, UV‐Vis, 1H, 13C{1H} and 19F{1H} NMR, and mass spectrometry. The antiproliferative effect of the new fluoroquinolone‐boron complexes in breast cancer (BC) derived cell lines MCF‐7 and SKBR‐3 was investigated. Compounds 9 b and 9 a showed antiproliferative in MCF‐7 cells, and 9 b, 11 b, 9 a, 7 a, 7b and 8 a showed similar effects in SKBR‐3 cells. Derivatives with p‐methoxybenzyl amino moieties at C‐7 and an ethyl or methyl group at N‐1 in the fluoroquinolone ring (9 a and 9 b) were the more efficient in both breast cancer cell lines. In addition, an 8‐nitro group to the fluoroquinolone (11 b) improved activity against SKBR‐3 cell proliferation. These compounds represent potential drug candidates for breast cancer treatment.

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Section: Discussionmentioning

confidence: 99%

Synthesis and Anticancer Activity of 1‐(Ethyl/Methyl)‐7‐(p‐Methoxybenzyl Amino) and 7‐Amino‐6‐Fluoroquinolone‐Boron Difluoride Complexes

Hernández‐López,

Tejada‐Rodríguez,

Leyva‐Ramos

et al. 2023

ChemistrySelect

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“…The majority of –NO 2 , 7,8‐imidazoline‐fused and 7,8‐imidazole‐fused FQs , and hexahydro‐2,7‐dioxopyrido[2,3‐f] quinolones exhibited weak to moderate potency, but the SAR was enriched.…”

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 novel 7-haloanilino-8-nitrofluoroquinolone derivatives

et al. 2011

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The synthesis of new 7-(halophenylamino)-1-cyclopropyl-6-fluoro-8-nitro-4-oxo-1,4-dihydroquinoline-3-carboxylic acid derivatives is described. Substitution of quinolonic compound 1a with chloro and fluoro aniline derivatives at position 7 produced target compounds 2-9 with relatively low yields. Alternatively, the product of correspondent carboxylate ester 1b subsequent with acid hydrolysis produced satisfactory yield. The prepared targets have shown interesting antibacterial properties against standard and resistant gram-positive strains. In particular, 2-chloro and 3-chloro aniline derivatives (3 and 4) depict MIC values of 6.7 and 0.9 lg/ml, respectively against standard S. aureous. Both compounds showed good activity against resistant strains of S. aureous.

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Synthesis and antibacterial properties of new N₄-acetylated hexahydro-2,7-dioxopyrido[2,3-f]quinoxaline-8-carboxylic acids

Cited by 8 publications

References 29 publications

Synthesis and Anticancer Activity of 1‐(Ethyl/Methyl)‐7‐(p‐Methoxybenzyl Amino) and 7‐Amino‐6‐Fluoroquinolone‐Boron Difluoride Complexes

Synthesis and Anticancer Activity of 1‐(Ethyl/Methyl)‐7‐(p‐Methoxybenzyl Amino) and 7‐Amino‐6‐Fluoroquinolone‐Boron Difluoride Complexes

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

Synthesis and antibacterial activity of novel 7-haloanilino-8-nitrofluoroquinolone derivatives

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Synthesis and antibacterial properties of new N4-acetylated hexahydro-2,7-dioxopyrido[2,3-f]quinoxaline-8-carboxylic acids

Cited by 8 publications

References 29 publications

Synthesis and Anticancer Activity of 1‐(Ethyl/Methyl)‐7‐(p‐Methoxybenzyl Amino) and 7‐Amino‐6‐Fluoroquinolone‐Boron Difluoride Complexes

Synthesis and Anticancer Activity of 1‐(Ethyl/Methyl)‐7‐(p‐Methoxybenzyl Amino) and 7‐Amino‐6‐Fluoroquinolone‐Boron Difluoride Complexes

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

Synthesis and antibacterial activity of novel 7-haloanilino-8-nitrofluoroquinolone derivatives

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Synthesis and antibacterial properties of new N₄-acetylated hexahydro-2,7-dioxopyrido[2,3-f]quinoxaline-8-carboxylic acids