Synthesis and antibacterial activity of new 4-alkoxy, 4-aminoalkyl and 4-alkylthioquinoline derivatives

Kayirere, Marie-Gratia; Mahamoud, Abdallah; Chevalier, Jacqueline; Soyfer, J. C.; Crémieux, A; Barbe, Jacques

doi:10.1016/s0223-5234(99)80076-2

Cited by 37 publications

(25 citation statements)

References 5 publications

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“…The robot automatically inoculated the microplate with a solution containing 10 6 cells. The results were read after 24 h at 37°C (14). for cefepime, 4 g/ml for cefpirome, 1 g/ml for ciprofloxacine, 8 g/ml for chloramphenicol, and 4 g/ml for tetracycline.…”

Section: Methodsmentioning

confidence: 99%

Imipenem Resistance of Enterobacter aerogenes Mediated by Outer Membrane Permeability

et al. 2000

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Multidrug-resistant Enterobacter aerogenes strains are increasingly isolated in Europe and especially in France. Treatment leads to imipenem resistance, because of a lack of porin. We studied the evolution of resistance in 29 strains isolated from four patients during their clinical course. These strains belonged to the prevalent epidemiological type observed in France in previous studies (C. Bosi, et al., J. Clin. Microbiol. 37:2165–2169, 1999; A. Davin-Regli et al., J. Clin. Microbiol. 34:1474–1480, 1996). They also harbored a TEM-24 extended-spectrum β-lactamase-coding gene. Thirteen strains were susceptible to gentamicin and resistant to imipenem and cefepime. All of the patients showed E. aerogenes strains with this resistance after an imipenem treatment. One patient showed resistance to imipenem after a treatment with cefpirome. Twelve of these 13 strains showed a lack of porin. Cessation of treatment with imipenem for three patients was followed by reversion of susceptibility to this antibiotic and the reappearance of porins, except in one case. For one patient, we observed three times in the same day the coexistence of resistant strains lacking porin and susceptible strains possessing porin. The emergence of multidrug-resistant E. aerogenes strains is very disquieting. In our study, infection by E. aerogenesincreased the severity of the patients' illnesses, causing a 100% fatality rate.

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Section: Methodsmentioning

confidence: 99%

Imipenem Resistance of Enterobacter aerogenes Mediated by Outer Membrane Permeability

et al. 2000

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“…We have studied ADME‐Tox properties of synthesized compounds ( 8a – 8s ) by using Ciprafloxacine, Quinine, Chloroquine, Isoniazid as a standard for the prediction of pharmacophore as well as drug likeness properties. Accelrys Discovery Studio was used for the ADME‐Tox (absorption, distribution, metabolism, excretion, and toxicity) properties and are listed in Table . Marvin suite program was used for the SD file format.…”

Section: Docking Studymentioning

confidence: 99%

Synthesis, Docking, ADME‐Tox Study of 2‐(2‐(2‐Chlorophenyl)quinoline‐4‐carbonyl)‐N‐substituted hydrazinecarbothioamide Derivatives and Their Biological Evaluation

Patel

Vekariya

Patel

et al. 2018

Journal of Heterocyclic Chem

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A series of 2‐(2‐(2‐chlorophenyl)quinoline‐4‐carbonyl)‐N‐substituted hydrazinecarbothioamide derivatives were synthesized by facile and efficient conventional method. The structures of the compounds were elucidated with the aid of an elemental analysis, IR, ESI‐MS, 1H‐NMR, and 13C‐NMR spectral data. The synthesized compounds were evaluated for their in vitro antibacterial, antifungal, antimalarial, and antituberculosis activity against standard drugs. The bacterial studies were determined against gram‐positive and negative bacteria. These compounds were found to a broad spectrum of activity against the screened bacteria, but poor activity was observed against Pseudomonas aeruginosa and Escherichia coli. Compounds 8d, 8f, 8i, 8l, and 8n showed the potent activity against Staphylococcus aureus. Compounds 8d, 8g, 8k, 8l, and 8q show the potent activity against antimalarial as compared with the standard drugs Chloroquine, Quinine and compounds 8h, 8n, and 8o shows mild activity against H37Rv strain. Molecular docking revealed that synthesized derivatives and target proteins were actively involved in a binding pattern and had a significant corelation with biological activity. We have also performed a molecular dynamics and ADME‐Tox parameters for the synthesized compounds.

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“…As a structural subunit in many natural products, the quinoline ring system is one of the most commonly encountered heterocycles in medicinal chemistry. A literature survey revealed that substituted quinolines possess diverse chemotherapeutic activities including antibacterial (Kayirere et al, 1998, Kidwai et al, 2000, antifungal (Musiol et al, 2006), anti-amoebic (Burkhaller & Edgerton, 1951;Bailey et al, 1979), antileishmanial (Dade et al, 2001;Jain et al, 2005), antimalarial (Charris et al, 2005;Cunico et al, 2006) and antitumor activities (Zhao et al, 2005;Chen et al, 2006). Furthermore, heterocyclic chalcone analogs, act as intermediate products in the synthesis of practically important flavonoids and themselves show useful biological activity (Dhar & Barton, 1981).…”

Section: Commentmentioning

confidence: 99%

(E)-3-(2-Ethoxyquinolin-3-yl)-1-(2-hydroxy-6-methylphenyl)prop-2-en-1-one

et al. 2007

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The title molecule, C21H19NO3, consists of a 2‐ethoxyquinolyl group linked to an aroylvinyl group. The quinolyl ring forms a dihedral angle of 2.88 (6)° with the benzene ring. The crystal structure can be described by two types of crossed layers which are parallel to (110) and (10). The packing is stabilized by C—H...O and O—H...O intra‐ and intermolecular hydrogen bonds, resulting in the formation of a two‐dimensional network.

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Synthesis and antibacterial activity of new 4-alkoxy, 4-aminoalkyl and 4-alkylthioquinoline derivatives

Cited by 37 publications

References 5 publications

Imipenem Resistance of Enterobacter aerogenes Mediated by Outer Membrane Permeability

Imipenem Resistance of Enterobacter aerogenes Mediated by Outer Membrane Permeability

Synthesis, Docking, ADME‐Tox Study of 2‐(2‐(2‐Chlorophenyl)quinoline‐4‐carbonyl)‐N‐substituted hydrazinecarbothioamide Derivatives and Their Biological Evaluation

(E)-3-(2-Ethoxyquinolin-3-yl)-1-(2-hydroxy-6-methylphenyl)prop-2-en-1-one

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