Preparation and biological assessment of some aromatic hydrazones derived from hydrazides of phenolic acids and aromatic aldehydes

Moussa, Ziad; Al-Mamary, Mohammed; Al-Juhani, Sultan; Ahmed, Saleh

doi:10.1016/j.heliyon.2020.e05019

Cited by 23 publications

(18 citation statements)

References 63 publications

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“…The stability of the phenoxy radical in this case is enhanced by the formation of an intramolecular hydrogen bond. Other studies [121][122][123] described the synthesis of different compounds like aromatic Schiff bases and aromatic hydrazones containing hydroxyl groups attached to different positions in the aromatic rings. These compounds were designed to mimic as much as possible natural phenolic compounds such as stilbene and chalcones.…”

Section: Stilbenesmentioning

confidence: 99%

Antioxidant Activity: The Presence and Impact of Hydroxyl Groups in Small Molecules of Natural and Synthetic Origin

Al-Mamary¹,

Moussa²

2021

Antioxidants - Benefits, Sources, Mechanisms of Action

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Polyhydroxylated natural phenolic compounds, especially those with low molecular weights, are characterized by their ability to eliminate free radicals as they act as strong antioxidants. The various types of phenolic compounds represent the most important natural antioxidants in addition to some vitamins. The chemical structures of these compounds is discussed in details with their action mechanisms to remove free radicals and prevent many incurable and malignant diseases. In addition to these natural compounds, the last two decades have witnessed increased attempts by many scientific groups and research centers to synthesize chemical compounds in large quantities to mimic these natural compounds, but at a lower cost and greater biological effectiveness. Herein, we conduct a chemical survey of relevant synthetic compounds containing the hydroxyl groups prepared in chemical laboratories and studied for their biological efficacies, such as their effectiveness as antioxidants, as well as the mechanism of elimination of free radicals.

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Section: Stilbenesmentioning

confidence: 99%

Antioxidant Activity: The Presence and Impact of Hydroxyl Groups in Small Molecules of Natural and Synthetic Origin

Al-Mamary¹,

Moussa²

2021

Antioxidants - Benefits, Sources, Mechanisms of Action

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“…These chelators and their synthetic complex derivatives have enormous benefit to acquire varied applications in several fields. They have shown considerable antimalarial, 1 anti-insecticidal, 2 anticancer, 3 anticholinesterase, 4 antitumor, 5,6 anti-tuberculosis, 7 antifungal, [8][9][10][11] antibacterial, 8-11 antihyperglycemic, 12,13 anti-infective, 14 antiradical, 15 antioxidant, [16][17][18] antimicrobial, 19,20 antitrypanosome, 21 antidiabetic, anti-inflammatory, 22,23 antiviral, [23][24][25] antidepressant and nootropic, 26 and gastroprotective activities. 27 Furthermore, They act as enzyme inhibitors, 23,[28][29][30] catalysts in various reactions, [31][32][33] and excellent anticorrosion to protect the metals and alloys as steel.…”

Section: Introductionmentioning

confidence: 99%

Metal complexes of hydrazone–oxime derivative as promising in vitro antimicrobial agents against some fungal and bacterial strains

Hassan

Ebrahium

2022

Applied Organom Chemis

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In this study, Cu2+, Co2+, Ni2+, Mn2+, Zn2+, Fe3+, VO2+, and UO22+ complexes derived from a NNO tridentate chelating hydrazone–oxime, namely, N′‐((2E,3Z)‐3‐(hydroxyimino)butan‐2‐ylidene)benzohydrazide (H2L,1) were prepared. The elemental, thermo‐gravimetric, spectral, molar conductivity, and magnetic measurements were applied to elucidate the compositions and structures of these new compounds. In addition to the density functional theory (DFT), studies were employed to acquire optimal structures and quantum chemical parameters. The analyses indicate that the chelator reacted as a neutral or mononegative tridentate ligand bonded to the metal ions via the enolic/ketonic carbonylic oxygen, protonated/deprotonated oximatic nitrogen, and azomethine nitrogen atoms adopting square planar or distorted octahedral geometry. The structural characterization of hydrazone–oxime and its complexes was supported by DFT calculations according to the DFT‐B3LYP procedure and 6‐311+G(d,p) basis set. The theoretical data revealed that the reactivity of the complexes is greater than the free hydrazone–oxime (H2L,1), and there is a good agreement between the practical and theoretical data. The thermogravimetric investigation shows that the complexes break down in two to four decomposing steps in temperature range extended from 50 to 1000°C. In vitro antimicrobial activity data demonstrated an increase in activity of the hydrazone–oxime (H2L,1), upon chelation, and some metal complexes show enhanced antibacterial and antifungal agents.

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“…The latter virtual simulation examines ranges based on the properties of 95 % of the known drugs and evaluates outliers based on Lipinski's rule of five. 14…”

Section: Prediction Of Adme Propertiesmentioning

confidence: 99%

Design, microwave-assisted synthesis, biological evaluation, molecular docking and ADME studies of pyrrole-based hydrazide-hydrazones as potential antioxidant agents

Mateev¹,

Georgieva²,

Zlatkov³

2022

Maced. J. Chem. Chem. Eng.

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In this study, one novel N-pyrrolyl carboxylic acid (3), the corresponding N-pyrrolyl hydrazide (5), and four new hydrazide-hydrazones (5a-d) bearing electron donating moieties were designed, synthesized, and fully elucidated by 1H NMR, FT-IR, and HRMS. The hydrazide-hydrazones were produced in five steps, which were optimized by applying microwave heating. The microwave-assisted synthesis significantly decreased the reaction times and increased the yields of the title molecules. In addition, all novel compounds were assessed for their radical scavenging properties by employing DPPH and ABTS assays. The most promising agent was obtained after condensation of the title hydrazide (5) with a 3,5-dimetoxy-4-hydroxybenzaldehyde (5d). The latter compound showed better antioxidant properties than Trolox (6-hydroxy-2,5,7,8-tetramethylchroman-2-carboxylic acid) and could serve as a prominent lead structure for future optimization as an antioxidant agent. A possible binding conformation of 5d in the active site of NADPH oxidase was also identified through molecular docking simulations. Analysis of the major interactions showed the importance of the hydroxyl moiety for the antioxidant activity. Finally, the virtual calculations of the ADME properties of the synthesized compounds displayed good drug-like properties. Overall, an optimized synthetic protocol through MW irradiation was employed. The newly synthesized ethyl (E)-5-(4-bromophenyl)-1-(1-(2-(4-hydroxy-3,5-dimethoxybenzylidene)hydrazineyl)-3-(1H-indol-3-yl)-1-oxopropan-2-yl)-2-methyl-1H-pyrrole-3-carboxylate (5d) was found to possess the most prominent radical-scavenging capacity, which identifies it as a promising lead compound for the development of novel antioxidants.

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Preparation and biological assessment of some aromatic hydrazones derived from hydrazides of phenolic acids and aromatic aldehydes

Cited by 23 publications

References 63 publications

Antioxidant Activity: The Presence and Impact of Hydroxyl Groups in Small Molecules of Natural and Synthetic Origin

Antioxidant Activity: The Presence and Impact of Hydroxyl Groups in Small Molecules of Natural and Synthetic Origin

Metal complexes of hydrazone–oxime derivative as promising in vitro antimicrobial agents against some fungal and bacterial strains

Design, microwave-assisted synthesis, biological evaluation, molecular docking and ADME studies of pyrrole-based hydrazide-hydrazones as potential antioxidant agents

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