New hydrazide-hydrazones and 1,3-thiazolidin-4-ones with 3-hydroxy-2-naphthoic moiety: Synthesis, in vitro and in vivo studies

Popiołek, Łukasz; Piątkowska‐Chmiel, Iwona; Gawrońska‐Grzywacz, Monika; Biernasiuk, Anna; Izdebska, Magdalena; Herbet, Mariola; Sysa, Marcin; Malm, Anna; Dudka, Jarosław; Wujec, Monika

doi:10.1016/j.biopha.2018.04.163

Cited by 36 publications

(37 citation statements)

References 37 publications

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“…[53] The very intense bands at 1683, 1604, 1,289, 1,093, and 1,015 cm −1 were assigned to the carbonyl ν(C=O) [28] and azomethine ν(C=N) groups, [54,55] and to the enolic ν(C-OH), ether ν(O-C-O), [56] and ν(N-N) [53] linkages, respectively. The coordination mode of the ligand was found by comparing the IR spectral data of complexes with that of the free hydrazone (1). This comparison shows that acetohydrazide 1 acts as a monobasic bidentate chelator in all the complexes.…”

Section: Infrared Spectramentioning

confidence: 99%

Transition metal complexes derived fromN′‐(4‐fluorobenzylidene)‐2‐(quinolin‐2‐yloxy) acetohydrazide: Synthesis, structural characterization, and biocidal evaluation

El‐Saied

Shakdofa

Al‐Hakimi

et al. 2020

Applied Organom Chemis

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complexes of a synthetic novel hydrazone containing a quinoline moiety were prepared. The composition and structure of the prepared compounds were elucidated by spectral and analytical techniques. The results reveal that all complexes were formed in 1:1 mole ratio except Mn 2+ and Cu 2+ complexes (3) and (7), which were formed in 1 M:2 L mole ratio. It was also found that the ligand binds the metal ions via NO donor sites as a monobasic bidentate chelator in all complexes through the enolic carbonyl oxygen and azomethine nitrogen atoms. The electronic absorption spectra and magnetic moment data demonstrated square pyramidal and octahedral geometries for the VO 2+ and Ni 2+ complexes, respectively, while the other complexes adopted tetrahedral geometry. The thermal decomposition of the complexes was discussed in relation to structure. The thermal analysis data demonstrated that all complexes were decomposed in one, two, three or four stages starting with the dehydration process, removal of coordination water molecules or elimination of anions and ended with the formation of the metal oxide. The bactericidal activities of the prepared compounds demonstrated that hydrazone (1) exerted a highly inhibitory effect against B. subtilis while VO 2+ , Co 2+ , and Cu 2+ complexes (2), (4), and (7) showed an inhibitory effect against E. coli more than the tetracycline. Additionally, the inhibitory effect of the prepared compound against A. niger showed that the Cu 2+ complex (6) is the most active while the Ni 2+ , Cu 2+ , and Zn 2+ complexes (5-8) exhibited an extremely inhibitory effect against C. albicans.

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Section: Infrared Spectramentioning

confidence: 99%

Transition metal complexes derived fromN′‐(4‐fluorobenzylidene)‐2‐(quinolin‐2‐yloxy) acetohydrazide: Synthesis, structural characterization, and biocidal evaluation

El‐Saied

Shakdofa

Al‐Hakimi

et al. 2020

Applied Organom Chemis

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“…The data obtained allow us to investigate the influence of different substituents on the antimicrobial activity of hydrazide‐hydrazones. In addition to this, in our earlier study hydrazide‐hydrazones of 3‐hydroxy‐2‐naphthoic acid also displayed significant anticancer activity against human renal cell adenocarcinoma (769‐P) and human hepatocellular carcinoma (HepG2) and proved to be safe towards normal reference cell lines (rat cardiomyocytes—H9c2 and green monkey kidney cells—GMK), which is very important in designing novel antimicrobial agents (Popiołek, Piątkowska‐Chmiel, et al, ).…”

Section: Introductionmentioning

confidence: 99%

Synthesis of promising antimicrobial agents: hydrazide‐hydrazones of 5‐nitrofuran‐2‐carboxylic acid

et al. 2019

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In this research, we synthesized and evaluated for in vitro antimicrobial activity a new series of hydrazide-hydrazones obtained from 5-nitrofuran-2-carboxylic acid.New compounds were identified and characterized by spectral methods ( 1 H NMR and 13 C NMR). All tested hydrazide-hydrazones proved to be promising antimicrobial agents. Antimicrobial activity and antifungal activity of new derivatives of 5-nitrofuran-2-carboxylic acid were revealed in many cases to be higher than the activity of reference substances (nitrofurantoin, cefuroxime and ampicillin). Yield: 47%; M.p.: 126°C; 1 H NMR (DMSO-d 6 ) δ (ppm): 2.09 (s, 3H, CH 3 ), 2.57-2.61 (t, 2H, CH 2 , J = 6 Hz), 2.68-2.74 (q, 2H, CH 2 , J = 6 Hz), 7.50-7.51 (d, 1H, ArH, J = 3 Hz), 7.78-7.79 (d, 1H, ArH, J = 3 Hz), 7.79-7.83 (t, 1H, =CH, J = 9 Hz, J = 3 Hz), 11.95 (s, 1H, NH); 13 C NMR (DMSO-d 6 ) δ (ppm): 14.6 (SCH 3 ), 30.3 (CH 2 ), 33.6 (CH 2 ), 115.4, 123.6, 138.2, 150.1 (4C ar ), 154.8 (=CH), 156.2 (C = O); For 262 | POPIOŁEK Et al.

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“…[45] Iproniazide, an isoniazid derivative, originally used as an antituberculosis medicine, showed mood elevation in depressed patients, which makes it the first MAO (monoamine oxidase) inhibitor. [46] Due to the broad spectrum of biological activity, especially antimicrobial activity of isonicotinic acid [44,45] and 1,3,4-oxadiazole derivatives, [10 -15] as well as that of hydrazide-hydrazones, reported by our group earlier, [47][48][49][50][51][52] we decided to combine these two pharmacophores in one chemical structure with the hope of obtaining interesting antimicrobial agents.…”

Section: Introductionmentioning

confidence: 99%

Synthesis andin VitroAntimicrobial Activity Screening of New 3‐Acetyl‐2,5‐disubstituted‐1,3,4‐oxadiazoline Derivatives

Popiołek

Biernasiuk

Paruch

et al. 2019

Chemistry & Biodiversity

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Thirteen new 3‐acetyl‐2,5‐disubstituted‐1,3,4‐oxadiazoline derivatives were synthesized from corresponding hydrazide‐hydrazones of isonicotinic acid in the reaction with acetic anhydride. The obtained compounds were identified with the use of spectral methods (IR, 1H‐NMR, 13C‐NMR, MS). In vitro antimicrobial activity screening of synthesized compounds against a panel of bacteria and fungi revealed interesting antibacterial and antifungal activity of tested 1,3,4‐oxadiazoline derivatives, which is comparable to that of commonly used antimicrobial agents.

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New hydrazide-hydrazones and 1,3-thiazolidin-4-ones with 3-hydroxy-2-naphthoic moiety: Synthesis, in vitro and in vivo studies

Cited by 36 publications

References 37 publications

Transition metal complexes derived fromN′‐(4‐fluorobenzylidene)‐2‐(quinolin‐2‐yloxy) acetohydrazide: Synthesis, structural characterization, and biocidal evaluation

Transition metal complexes derived fromN′‐(4‐fluorobenzylidene)‐2‐(quinolin‐2‐yloxy) acetohydrazide: Synthesis, structural characterization, and biocidal evaluation

Synthesis of promising antimicrobial agents: hydrazide‐hydrazones of 5‐nitrofuran‐2‐carboxylic acid

Synthesis andin VitroAntimicrobial Activity Screening of New 3‐Acetyl‐2,5‐disubstituted‐1,3,4‐oxadiazoline Derivatives

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