Synthesis, structure and biological activity of hydrazones derived from 2- and 4-hydroxybenzoic acid hydrazides

Nurkenov, Oralgazy A.; Fazylov, Serik D.; Satpaeva, Zhanarkul B.; Seilkhanov, Tulegen M.; Turdybekov, Dastan M.; Mendibayeva, Anel Zh.; Akhmetova, Saule B.; Shulgau, Zarina T.; Alkhimova, Larisa E.; Kulakov, Ivan V.

doi:10.1016/j.cdc.2023.101089

Cited by 3 publications

(3 citation statements)

References 49 publications

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“…The more complex second group, shown in Table 2, contains ten disubstituted molecules ( [13][14][15][16][17][18][19][20][21][22], derivatives of vanillic aldehyde and salicylic aldehydes with OH, Br, C 6 H 4 , tBu, and OCH 3 substituents. Thirteen derivatives ( [23][24][25][26][27][28][29][30][31][32][33][34][35] with three or more substituents were assigned to the most complicated third group, which are formally salicylic aldehyde derivatives with OH, OCH 3 , CH 2 OH, CH 3 , isopropyl, and tBu, as given in Table 3.…”

Section: Antifungal Activitiesmentioning

confidence: 99%

“…To date, many studies have been carried out on aryl OH-substituted hydrazidehydrazones (see Figure 1), covering several biological aspects, such as antimicrobial [31][32][33][34][35], antiviral [33,[36][37][38][39], anticancer [40][41][42][43], antiradical [31,44], enzyme inhibitors [40, [44][45][46][47][48][49], cytotoxicity [36,50], and photophysical activity [51,52]. Recently, Mali et al [33] and Popiołek [32] published exhaustive, comprehensive reviews on the biological activity, including antimicrobial activity, of hydrazides and their derivatives.…”

Section: Introductionmentioning

confidence: 99%

“…Several articles described the examples of aryl-OH-substituted hydrazide-hydrazones in the context of the antibacterial, antifungal, and antiviral activities. For instance, the derivatives of 2-chloro- 6-fluorobenzaldehyde with salicylic acid and 4-hydroxybenzoic acid hydrazides Ia and Ib, respectively, were active against the Gram-positive bacterium Bacillus subtilis [31]. In other studies, the 4-hydroxybenzaldehyde derivative of 2-[(1-methyl-1H-tetrazol-5yl)thio)acetohydrazide (II) showed weak anticandidal activities (MIC 0.5-1.0 mg/mL) compared to ketoconazole (MIC 1-31 µg/mL) and promising anticancer activity against NIH3T3 cell line with IC 50 = 0.632 mM [34].…”

Section: Introductionmentioning

confidence: 99%

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4-Hydroxybenzoic Acid-Based Hydrazide–Hydrazones as Potent Growth Inhibition Agents of Laccase-Producing Phytopathogenic Fungi That Are Useful in the Protection of Oilseed Crops

Maniak,

Matyja,

Pląskowska

et al. 2024

Molecules

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The research on new compounds against plant pathogens is still socially and economically important. It results from the increasing resistance of pests to plant protection products and the need to maintain high yields of crops, particularly oilseed crops used to manufacture edible and industrial oils and biofuels. We tested thirty-five semi-synthetic hydrazide–hydrazones with aromatic fragments of natural origin against phytopathogenic laccase-producing fungi such as Botrytis cinerea, Sclerotinia sclerotiorum, and Cerrena unicolor. Among the investigated molecules previously identified as potent laccase inhibitors were also strong antifungal agents against the fungal species tested. The highest antifungal activity showed derivatives of 4-hydroxybenzoic acid and salicylic aldehydes with 3-tert-butyl, phenyl, or isopropyl substituents. S. sclerotiorum appeared to be the most susceptible to the tested compounds, with the lowest IC50 values between 0.5 and 1.8 µg/mL. We applied two variants of phytotoxicity tests for representative crop seeds and selected hydrazide–hydrazones. Most tested molecules show no or low phytotoxic effect for flax and sunflower seeds. Moreover, a positive impact on seed germination infected with fungi was observed. With the potential for application, the cytotoxicity of the hydrazide–hydrazones of choice toward MCF-10A and BALB/3T3 cell lines was lower than that of the azoxystrobin fungicide tested.

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Section: Antifungal Activitiesmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

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4-Hydroxybenzoic Acid-Based Hydrazide–Hydrazones as Potent Growth Inhibition Agents of Laccase-Producing Phytopathogenic Fungi That Are Useful in the Protection of Oilseed Crops

Maniak,

Matyja,

Pląskowska

et al. 2024

Molecules

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Synthesis, characterization, antimicrobial and anti-biofilm studies of Ni(II) complex with Schiff base derived from 2-thiophene carboxaldehyde and phenyl acetic hydrazide

Çınarlı,

Kıray,

Ataol

2024

Journal of Molecular Structure

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Synthesis and Biological Activity of New Hydrazones Based on N-Aminomorpholine

Nurkenov,

Zhautikova,

Khlebnikov

et al. 2024

Molecules

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The data on the synthesis of N-aminomorpholine hydrazones are presented. It is shown that the interaction of N-aminomorpholine with functionally substituted benzaldehydes and 4-pyridinaldehyde in isopropyl alcohol leads to the formation of corresponding hydrazones. The structure of the synthesized compounds was studied by 1H and 13C NMR spectroscopy methods, including the COSY (1H-1H), HMQC (1H-13C) and HMBC (1H-13C) methodologies. The values of chemical shifts, multiplicity, and integral intensity of 1H and 13C signals in one-dimensional NMR spectra were determined. The COSY (1H-1H), HMQC (1H-13C), and HMBC (1H-13C) results revealed homo- and heteronuclear interactions, confirming the structure of the studied compounds. The antiviral, cytotoxic, and antimicrobial activity of some synthesized hydrazones were investigated. It is shown that 2-((morpholinoimino)methyl)benzoic acid has a pronounced viral inhibitory property, comparable in its activity to commercial drugs Tamiflu and Remantadine. A docking study was performed using the influenza virus protein models (1930 Swine H1 Hemagglutinin and Neuraminidase of 1918 H1N1 strain). The potential binding sites that are complementary with 2-((morpholinoimino)methyl)benzoic acid were found.

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Synthesis, structure and biological activity of hydrazones derived from 2- and 4-hydroxybenzoic acid hydrazides

Cited by 3 publications

References 49 publications

4-Hydroxybenzoic Acid-Based Hydrazide–Hydrazones as Potent Growth Inhibition Agents of Laccase-Producing Phytopathogenic Fungi That Are Useful in the Protection of Oilseed Crops

4-Hydroxybenzoic Acid-Based Hydrazide–Hydrazones as Potent Growth Inhibition Agents of Laccase-Producing Phytopathogenic Fungi That Are Useful in the Protection of Oilseed Crops

Synthesis, characterization, antimicrobial and anti-biofilm studies of Ni(II) complex with Schiff base derived from 2-thiophene carboxaldehyde and phenyl acetic hydrazide

Synthesis and Biological Activity of New Hydrazones Based on N-Aminomorpholine

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