Synthesis and Biological Activity of Quinoline-2-Carboxylic Acid Aryl Esters and Amides

Boyarshinov, V. D.; Mikhalev, A. I.; Yushkova, T. A.; Ukhov, S. V.; Kon'shina, T. M.

doi:10.1007/s11094-017-1613-4

Cited by 7 publications

(4 citation statements)

References 1 publication

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“…Synthesis. 2-Chloroquinoline-3-carbaldehyde and 2chloro-8-methylquinoline-3-carbaldehyde were prepared by the literature report method [23,25].…”

Section: 2mentioning

confidence: 99%

“…Firstly, 2-chloroquinoline-3-carbaldehyde (1) and 2chloro-8-methylquinoline-3-carbaldehydes (5) were, respectively, synthesized from acetanilide and 2-methylacetanilide by utilizing the Vilsmeier reaction which involves treating the corresponding acetanilide analogs with POCl 3 in DMF mixture [23,25].…”

Section: Synthesis In the Present Work A New Series Of [23′mentioning

confidence: 99%

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Synthesis, Antibacterial, Antioxidant, and Molecular Modeling Studies of Novel [2,3′-Biquinoline]-4-Carboxylic Acid and Quinoline-3-Carbaldehyde Analogs

Zeleke

Melaku

Belay

et al. 2021

Journal of Chemistry

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Currently, it has been common to see people being affected and dying from untreatable infections caused by multidrug-resistant (MDR) germs. To tackle this problem, developing new effective chemotropic agents is urgently needed. Hence, this project aims to design, synthesize, and evaluate their antibacterial and antioxidant activities of new series of [2,3′-biquinoline]-4-carboxylic acid and quinoline-3-carbaldehyde analogs. The molecular docking analysis of the compounds against E. coli DNA gyrase was computed to investigate the binding mode of the compounds within the active site of the enzyme. In this regard, a new series of [2,3′-biquinoline]-4-carboxylic acid and quinoline-3-carbaldehyde analogs were synthesized by utilization of Vilsmeier–Haack, Doebner, nucleophilic substitution, and hydrolysis reactions. The structures of the synthesized compounds were determined using UV-Vis, FT-IR, and NMR. The synthesized compounds were screened for their antibacterial activity against four bacterial strains using disc diffusion methods. The findings of the study revealed that seven of synthetic compounds possess good antibacterial activity compared to ciprofloxacin which was used as a positive control in the experiment. Among them, compounds 4, 9, and 10 displayed the highest mean inhibition zone of 13.7 ± 0.58, 16.0 ± 1.7, and 20.7 ± 1.5 mm, respectively, at 0.1 μg/μL. The radical scavenging property of these compounds was evaluated using DPPH radical assay where compounds 9 and 20 showed the strongest activity with IC50 values of 1.25 and 1.75 μg/mL, respectively. At the same concentration, the IC50 value of ascorbic acid was 4.5 μg/mL. The synthesized compounds were also assessed for their in silico molecular docking analysis. Compounds 4 (−6.9 kcal/mol), 9 (−6.9 kcal/mol), and 10 (−7.9 kcal/mol) showed the maximum binding affinity close to ciprofloxacin (−7.2 kcal/mol) used as a positive control. Thus, compounds 4, 9, and 10 showed the best antibacterial activities in both in vitro and molecular docking analyses among the synthetic compounds. The results of in silico molecular docking evaluation of the synthetic compounds against E. coli DNA gyrase B were in good agreement with the in vitro antibacterial analysis. Therefore, the antibacterial activity displayed by these compounds is encouraging for further investigation to improve the activities of [2,3′-biquinoline]-4-carboxylic acid by incorporating various bioisosteric groups in either of the quinoline rings.

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“…Synthesis. 2-Chloroquinoline-3-carbaldehyde and 2chloro-8-methylquinoline-3-carbaldehyde were prepared by the literature report method [23,25].…”

Section: 2mentioning

confidence: 99%

Section: Synthesis In the Present Work A New Series Of [23′mentioning

confidence: 99%

Synthesis, Antibacterial, Antioxidant, and Molecular Modeling Studies of Novel [2,3′-Biquinoline]-4-Carboxylic Acid and Quinoline-3-Carbaldehyde Analogs

Zeleke

Melaku

Belay

et al. 2021

Journal of Chemistry

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“…Za izražavanje akutne toksičnosti se koristi koncentracija jedinjenja koja dovodi do imobilizacije 50% jedinki populacije izložene njegovom dejstvu tokom unapred definisanog vremenskog perioda (najčešće 48h) i označava se kao efektivna koncentracija, EC50 [17]. Imajući u vidu da amidi predstavljaju veliku i raznovrsnu grupu biološki aktivnih molekula sa širokom primenom u medicini [18][19][20][21][22][23], poljoprivredi [24][25][26] i biotehnologiji [27,28] u ovom radu je proučavano hromatografsko ponašanje i lipofilnost odabranih derivata cijanoacetamida, primenom tankoslojne hromatografije na obrnutim fazama u smeši vode i tri organska modifikatora ponaosob (tbutanola, N,N,-dimetilformamida (DMF) i dimetilsulfoksida (DMSO)). Primenom metode linearne regresije je ispitana zavisnost između dobijenih hromato-grafskih parametara (RM0 i m) i softverski iz-računatih vrednosti podeonog koeficijenta, log P, kao i odabranih farmakokinetičkih prediktora, odnosno parametara toksičnosti proučavanih derivata cijanoacetamida.…”

Section: Uvodunclassified

Studying of lipophilicity of potential biological active cyanoacetamide derivatives

Apostolov¹,

Vaštag²

2017

J. eng. process. manag.

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Primenom pravila Lipinskog za odabrane derivate cijanoacetamida je teorijski ispitana mogućnost postojanja njihove biološke aktivnosti. Lipofilnost proučavanih cijanoacetamida je određena primenom odgovarajućih softverskih paketa i tankoslojnom hromatografijom na obrnutim fazama (RP TLC18 F254s) u sistemima voda-t-butanol, voda-dimetilformamid i voda-dimetilsulfoksid. Dobijeni hromatografski parametri, RM0 i m su metodom linearne regresije korelisani sa podeonim koeficijentom, log P, kao standardnim merilom lipofilnosti, važnim farmakokinetičkim parametrima i odabranim parametrima toksičnosti. Uspostavljene linearne zavisnosti su opisane visokim vrednostima regresionog koeficijenta, r, čime je pokazano da RP TLC18 F254s omogućava pouzdano određivanje lipofilnosti derivata cijanoacetamida kao potencijalno bioaktivnih jedinjenja.

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“…Quinoline derivatives are heterocyclic compounds that are widely used as antibacterial, bactericidal, anti-allergic, antidepressant, antihypertensive, antitumor, and antimalarial agents. [10][11][12][13] Quinoline carboxylic acid derivatives are multidentate organic ligands containing nitrogen atoms and carboxyl oxygen atoms which can coordinate with metal ions. The coordination modes of the carboxyl groups vary at different pH values, resulting in more coordination modes.…”

Section: Introductionmentioning

confidence: 99%

Preparation, crystal structures, properties, and time-dependent density functional theory of two cobalt complexes with 3-hydroxy-2-methyl-quinoline-4-carboxylate

Lai

Yan

et al. 2020

Journal of Chemical Research

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One organic compound [HMCA]2 (1) and two novel cobalt complexes [Co(MCA)(bipy)(H2O)]·(H2O) (2), [Co2(MCA)2(Phen)3]·3(H2O) (3) are synthesized by a solvothermal approach and are structurally determined by single-crystal X-ray diffraction. Compound 1 exhibits a two-dimensional structure by hydrogen bond and π. . .π stacking interaction. The complexes exhibit a three-dimensional and one-dimensional metal-organic framework. Solid-state photoluminescence spectrums reveal that they show blue emission bands at 449 nm, and theoretical calculation results of time-dependent density functional theory show that all belong to ligand-to-ligand charge transfer. Solid-state diffuse reflectance spectrums reveal the presence of a narrow optical band gap of 1.72 and 1.60 eV in the complexes 2 and 3, respectively.

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Synthesis and Biological Activity of Quinoline-2-Carboxylic Acid Aryl Esters and Amides

Cited by 7 publications

References 1 publication

Synthesis, Antibacterial, Antioxidant, and Molecular Modeling Studies of Novel [2,3′-Biquinoline]-4-Carboxylic Acid and Quinoline-3-Carbaldehyde Analogs

Synthesis, Antibacterial, Antioxidant, and Molecular Modeling Studies of Novel [2,3′-Biquinoline]-4-Carboxylic Acid and Quinoline-3-Carbaldehyde Analogs

Studying of lipophilicity of potential biological active cyanoacetamide derivatives

Preparation, crystal structures, properties, and time-dependent density functional theory of two cobalt complexes with 3-hydroxy-2-methyl-quinoline-4-carboxylate

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