Pyridonecarboxylic acids as antibacterial agents. Synthesis and antibacterial activity of 7-(3-amino-1-pyrrolidinyl)-1-ethyl-6-fluoro-1,4-dihydro-4-oxo-1,8-naphthyridine-3-carboxylic acid and its analogs

Egawa, Hiroshi; Miyamoto, Teruyuki; Minamida, Akira; Nishimura, Yoshihiko; Okada, Hidetsugu; Uno, Hitoshi; Matsumoto, Junichi

doi:10.1021/jm00378a004

Cited by 46 publications

(20 citation statements)

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“…Most of the thiazoloquinolone derivatives were more cytotoxic than thiazetoquinolone derivatives against mammalian cells. 6-Fluoro-1-methyl-4-oxo-7-(1-piperazinyl)-4H- [1,3]thiazeto[3,2-a]quinoline-3-carboxylic acid (36) showed the most potent antibacterial activity of all compounds tested, as well as a very low cytotoxicity. This compound showed antibacterial activity and cytotoxicity comparable to that of ciprofloxacin [52].…”

Section: Thiazolo Derivativesmentioning

confidence: 99%

1,8‐Naphthyridine Derivatives: A Review of Multiple Biological Activities

Madaan

Verma

Kumar

et al. 2015

Archiv der Pharmazie

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The 1,8-naphthyridine group of compounds have gained special attention of researchers on account of their demonstrating a variety of interesting biological activities. A wide range of biological properties establishes them as potent scaffolds in therapeutic and medicinal research. The broad spectrum of activities primarily includes antimicrobial, antiviral, anticancer, anti-inflammatory, and analgesic activities. 1,8-Naphthyridine derivatives have also exhibited potential applications in neurological disorders such as Alzheimer's disease, multiple sclerosis, and depression. In addition, these synthetic derivatives have been found to possess activities such as anti-osteoporotic (α(v)β(3) antagonists), anti-allergic, antimalarial, gastric antisecretory, bronchodilator, anticonvulsant, anti-hypertensive, platelet aggregation inhibition, anti-oxidant, EGFR inhibition, protein kinase inhibition, ionotropic agent, β-3 antagonist, MDR modulator, adenosine receptor agonist, adrenoceptor antagonist, and pesticide activities. In spite of the widespread application of the 1,8-naphythyridine scaffolds, only a limited number of review articles are available till date. In this review, we attempt to compile and discuss the key data available in the literature for the multiple biological activities of 1,8-naphthyridine derivatives, in a chronological manner. This review compilation (with 199 references) may be helpful in understanding the diverse biological properties of 1,8-naphthyridines and provide insights into their mechanism of action. This may direct future research in the synthesis of new derivatives and exploring this scaffold for other possible biological activities.

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Section: Thiazolo Derivativesmentioning

confidence: 99%

1,8‐Naphthyridine Derivatives: A Review of Multiple Biological Activities

Madaan

Verma

Kumar

et al. 2015

Archiv der Pharmazie

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“…Many of the naphthyridines have shown bacterial, fungicidal and carcinogenic activities [3][4][5][6]. In recent past, study on derivatives of 1,8-naphthyridine has been concentrated as these compounds show a broad spectrum of biological activities [7][8][9][10][11][12][13][14][15]. A very few reports available on synthesis of urea derivative on naphthyridine.…”

Section: Introductionmentioning

confidence: 99%

“…7, 155.4, 153.7, 149.1, 138.8, 138.2, 137.1, 129.3, 121.8, 121.4, 119.5, 115.8, 115.2, 112.7; 222.19 (M+1).…”

mentioning

confidence: 99%

Synthesis and Antimicrobial Activity of Novel 1-[3-(1,8-Naphthyridin-2-yl)phenyl]-3-arylurea Derivatives

Bhasker¹,

Satyanarayana²,

Latha³

et al. 2018

Asian J. Chem.

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Asian Journal of Chemistry; Vol. 30, No. 4 (2018), [771][772][773][774] and only diagnostic and/or intense peaks are reported. 1H NMR spectra were recorded in DMSO-d 6 with a Varian Mercury plus 400 MHz instrument. Signals due to residual protonated solvent ( 1 H NMR) served as the internal standard. All the chemical shifts were presented in δ (ppm) using TMS as an internal standard. The 1 H NMR chemical shifts and coupling constants were determined assuming first-order behaviour. Mass spectra were recorded with a PE Sciex model API 3000 instrument. All the reactions were carried out under argon atmosphere.Biological assay: The synthesized compounds were dissolved in dimethyl sulphoxide at 30 µg/µL concentration (standard antibacterial drug, ampicilline was used as the reference antibiotic) and tested against Gram-negative strains of Escherichia coli, Klebsiella pneumonia and Gram-positive strains of Staphylococcus aureus and Bacillus subtilis using agar well diffusion method. Activities were determined by zones showing complete inhibition (mm). Growth inhibition was calculated with reference to positive control. All the samples were taken in triplicates.Synthesis of 2-(3-Nitrophenyl)-1,8-naphthyridine (3): To a stirred solution of 2-aminonicotinaldehyde (1 g, 8.18 mmol) in ethyl alcohol (20 mL) was added 1-(3-nitrophenyl)-ethanone (1.48 g, 9.00 mmol) and piperidine (2.09 g, 24.56 mmol) at room temperature and refluxed for 16 h. After completion of the reaction (monitored by TLC), the mixture was concentrated under reduced pressure and the crude product washed with 10 % dichloromethane in diethyl ether to afford 2-(3-nitrophenyl)-1,8-naphthyridine (3).Off Synthesis of 3-(1,8-naphthyridin-2-yl)aniline (4): To a stirred suspension of raney nickel (0.92 g, 10.75 mmol) in ethyl alcohol (20 mL) was added 2-(3-nitrophenyl)-1,8-naphthyridine (1 g, 3.58 mmol) and hydrazine hydrate (80 %) (0.54 g, 10.75 mmol) at room temperature and stirred at room temperature for 3 h. After completion of the reaction (monitored by TLC), the mixture was filtered through celite pad and the filtrate was concentrated under reduced pressure. The crude product was washed with 10 % dichloromethane in diethyl ether to afford 3-(1,8-naphthyridin-2-yl)aniline (4).IR ( δ 159. 7, 155.4, 153.7, 149.1, 138.8, 138.2, 137.1, 129.3, 121.8, 121.4, 119.5, 115.8, 115.2, 112.7; 222.19 (M+1). Synthesis of phenyl phenylcarbamate derivatives (5a-q):To a stirred solution of anilines (3.29 mmol) in dichloromethane (6 mL) was added triethylamine (9.89 mmol) at room temperature and stirred at room temperature for 10 min and added aryl chloro formate (4.93 mmol) at 0 °C and stirred at room temperature for 2 h. The reaction mixture was concentrated under reduced pressure and the crude material washed with 10 % diethyl ether in pentane to afford the pure compounds. Without further purification used for next step. Yields of the products varied between 65 to 85 %.Preparation of novel 1-[3-(1,8-naphthyridin-2-yl)phenyl]-3-phenylurea derivatives (6a-6q): To a stirred ...

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“…The main driving force towards the synthesis of naphthyridine is the search for compounds of therapeutic importance 1, 2 . 1,8-Naphthyridine derivatives represent one of the most active classes of compound possessing a wide spectrum of biological activities such as antifungal 3 , antitumor 4 , antimalarial 5 anti-inflammatory 6 and antihypertensive 7 .…”

Section: Introductionmentioning

confidence: 99%

One pot Two component Synthesis of linkers of Coumarine [1,8]Naphthyridine Derivatives

2017

IJMTER

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Abstract-In this paper we wish to report a one-pot synthesis of Coumarine [1,8]Naphthyridine derivatives by microwave irradiation under green protocol. Coumarins, also known as benzopyrones, are present in remarkable amounts in plants, although their presence has also been detected in microorganisms and animal sources. The Starting material 4-(2-bromoethoxy)-2H-chromen-2-one(2) and 3-Aryl-1,8-naphthyridin-2(1H)-one (3) were mixed in DMF and add potassium carbonate, the mixture was subjected to microwave irradiation at 800 W at 30 sec intervals for specified time showed after completion of the reaction (monitored by TLC), the reaction mixture was cooled to RT. Cold water added to the reaction mixture then solid precipitated is formed. The solid separated was filtered and purified by recrystallization from methanol to furnish a series of products 1-(2-((2-oxo-2H-chromen-4-yl)oxy)ethyl)-3-Aryl-1,8-naphthyridin-2(1H)-one.(4a-4o)(Scheme 1,2)(Table I,2).Compound (2) is prepared by the reaction between 4-hydroxy coumarin (1) and 1,2 dibromoetane by K 2 CO 3 under DMF above 85-90 0 C.

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Pyridonecarboxylic acids as antibacterial agents. Synthesis and antibacterial activity of 7-(3-amino-1-pyrrolidinyl)-1-ethyl-6-fluoro-1,4-dihydro-4-oxo-1,8-naphthyridine-3-carboxylic acid and its analogs

Cited by 46 publications

References 0 publications

1,8‐Naphthyridine Derivatives: A Review of Multiple Biological Activities

1,8‐Naphthyridine Derivatives: A Review of Multiple Biological Activities

Synthesis and Antimicrobial Activity of Novel 1-[3-(1,8-Naphthyridin-2-yl)phenyl]-3-arylurea Derivatives

One pot Two component Synthesis of linkers of Coumarine [1,8]Naphthyridine Derivatives

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