Combined experimental and theoretical studies of the structure-antiradical activity relationship of heterocyclic hydrazone compounds

Khodja, Imène Amine; Bensouici, Chawki; Boulebd, Houssem

doi:10.1016/j.molstruc.2020.128858

Cited by 13 publications

(3 citation statements)

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“…It was found that the synthesized new derivatives exhibited antioxidant activity comparable to those of ascorbic acid and Trolox [ 11 ]. In another study [ 12 ], twelve heterocyclic compounds bearing hydrazone functional groups were evaluated for antioxidant activity using DPPH, ABTS, and DMSO alkaline assays. The results showed that these heterocyclic compounds are potent antiradical agents [ 12 ].…”

Section: Introductionmentioning

confidence: 99%

“…In another study [ 12 ], twelve heterocyclic compounds bearing hydrazone functional groups were evaluated for antioxidant activity using DPPH, ABTS, and DMSO alkaline assays. The results showed that these heterocyclic compounds are potent antiradical agents [ 12 ]. In addition, a preliminary study performed by Tzankova et al [ 13 ] identified the promising radical scavenging potential of pyrrole-based hydrazones, as determined through DPPH and ABTS assays, which pointed our attention toward the synthesis of analogous representatives in an attempt to enrich the variety of molecules.…”

Section: Introductionmentioning

confidence: 99%

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Synthesis, DFT Study, and In Vitro Evaluation of Antioxidant Properties and Cytotoxic and Cytoprotective Effects of New Hydrazones on SH-SY5Y Neuroblastoma Cell Lines

Tzankova,

Kuteva,

Mateev

et al. 2023

Pharmaceuticals

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A series of ten new hydrazide–hydrazone derivatives bearing a pyrrole ring were synthesized and structurally elucidated through appropriate spectral characteristics. The target hydrazones were assessed for radical scavenging activity through 1,1-diphenyl-2-picrylhydrazyl (DPPH) and 2,2′-azino-bis(3-ethylbenzothiazoline-6-sulphonic acid) (ABTS) tests, with ethyl 5-(4-bromophenyl)-1-(2-(2-(4-hydroxy-3,5-dimethoxybenzylidene)hydrazine-yl)-2-oxoethyl)-2-methyl-1H-pyrrole-3-carboxylate (7d) and ethyl 5-(4-bromophenyl)-1-(3-(2-(4-hydroxy-3,5-dimethoxybenzylidene) hydra zine-yl)-3-oxopropyl)-2-methyl-1H-pyrrole-3-carboxylate (8d) highlighted as the best radical scavengers from the series. Additional density functional theory (DFT) studies have indicated that the best radical scavenging ligands in the newly synthesized molecules are stable, do not decompose into elements, are less polarizable, and with a hard nature. The energy of the highest occupied molecular orbital (HOMO) revealed that both compounds possess good electron donation capacities. Overall, 7d and 8d can readily scavenge free radicals in biological systems via the donation of hydrogen atoms and single electron transfer. The performed in vitro assessment of the compound’s protective activity on the H2O2-induced oxidative stress model on human neuroblastoma cell line SH-SY5Y determined 7d as the most perspective representative with the lowest cellular toxicity and the highest protection.

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Section: Introductionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Synthesis, DFT Study, and In Vitro Evaluation of Antioxidant Properties and Cytotoxic and Cytoprotective Effects of New Hydrazones on SH-SY5Y Neuroblastoma Cell Lines

Tzankova,

Kuteva,

Mateev

et al. 2023

Pharmaceuticals

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“…The rationale for studying the anticancer activity in this class of molecules is the fact that the heterocyclic hydrazones designed and described earlier showed significant antiproliferative activity in human tumor cells [ 18 ]. In turn, the justification for testing the ability to inhibit oxidative hemolysis by these compounds is that the previously described hybrids containing the 4,5-dihydro-1 H -imidazole template showed the highest antioxidant activity among hydrazones with various heterocyclic rings [ 19 ].…”

Section: Introductionmentioning

confidence: 99%

Thermal Decomposition Path—Studied by the Simultaneous Thermogravimetry Coupled with Fourier Transform Infrared Spectroscopy and Quadrupole Mass Spectrometry—Of Imidazoline/Dimethyl Succinate Hybrids and Their Biological Characterization

et al. 2023

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The thermal decomposition path of synthetically and pharmacologically useful hybrid materials was analyzed in inert and oxidizing conditions for the first time and presented in this article. All the imidazoline/dimethyl succinate hybrids (1–5) were studied using the simultaneous thermogravimetry (TG) coupled with Fourier transform infrared spectroscopy (FTIR) and quadrupole mass spectrometry (QMS). It was found that the tested compounds were thermally stable up to 200–208 °C (inert conditions) and up to 191–197 °C (oxidizing conditions). In both furnace atmospheres, their decomposition paths were multi-step processes. At least two major stages (inert conditions) and three major stages (oxidizing conditions) of their decomposition were observed. The first decomposition stage occurred between T5% and 230–237 °C. It was connected with the breaking of one ester bond. This led to the emission of one methanol molecule and the formation of radicals capable of further radical reactions in both used atmospheres. At the second decomposition stage (Tmax2) between 230–237 °C and 370 °C (inert conditions), or at about 360 °C (oxidizing conditions), the cleavage of the second ester bond and N-N and C-C bonds led to the emission of CH3OH, HCN, N2, and CO2 and other radical fragments that reacted with each other to form clusters and large clusters. Heating the tested compounds to a temperature of about 490 °C resulted in the emission of NH3, HCN, HNCO, aromatic amines, carbonyl fragments, and the residue (Tmax2a) in both atmospheres. In oxidizing conditions, the oxidation of the formed residues (Tmax3) was related to the production of CO2, CO, and H2O. These studies confirmed the same radical decomposition mechanism of the tested compounds both in inert and oxidizing conditions. The antitumor activities and toxicities to normal cells of the imidazoline/dimethyl succinate hybrids were also evaluated. As a result, the two hybrid materials (3 and 5) proved to be the most selective in biological studies, and therefore, they should be utilized in further, more extended in vivo investigations.

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Preparation and Characterization of Chitosan Derivatives Bearing Imidazole Ring with Antioxidant, Antibacterial, and Antifungal Activities

Zhang

et al. 2023

Starch Stärke

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In this study, three series of chitosan derivatives bearing imidazole rings, including the Schiff-bases of chitosan, N-substituted chitosan, and quaternized chitosan are designed and synthesized. The structures of these chitosan derivatives are verified by FT-IR and 1 H NMR, and their antioxidant, antibacterial, and antifungal activities are tested. The Schiff-bases of chitosan and N-substituted chitosan have similar biological properties compared with chitosan. Derivatives 2IMTMC, 4IMTMC, MIMTMC, and BIMTMC exhibit significant antioxidant ability and antifungal activity, especially derivative BIMTMC. All the quaternized chitosan remarkably inhibits Escherichia coli, Staphylococcus aureus, and Vibrio harvey, especially derivative BIMTMC, whose minimum inhibitory concentration values are 0.03125, 0.0625, and 0.03125 mg mL −1 , respectively. The results indicated that quaternized chitosan are synergistic with imidazole groups and have the better antioxidant, antifungal, and antibacterial properties than chitosan, which can be used as drug materials for antioxididant and antimicrobial purposes.

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Combined experimental and theoretical studies of the structure-antiradical activity relationship of heterocyclic hydrazone compounds

Cited by 13 publications

References 68 publications

Synthesis, DFT Study, and In Vitro Evaluation of Antioxidant Properties and Cytotoxic and Cytoprotective Effects of New Hydrazones on SH-SY5Y Neuroblastoma Cell Lines

Synthesis, DFT Study, and In Vitro Evaluation of Antioxidant Properties and Cytotoxic and Cytoprotective Effects of New Hydrazones on SH-SY5Y Neuroblastoma Cell Lines

Thermal Decomposition Path—Studied by the Simultaneous Thermogravimetry Coupled with Fourier Transform Infrared Spectroscopy and Quadrupole Mass Spectrometry—Of Imidazoline/Dimethyl Succinate Hybrids and Their Biological Characterization

Preparation and Characterization of Chitosan Derivatives Bearing Imidazole Ring with Antioxidant, Antibacterial, and Antifungal Activities

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