Design, Synthesis, Molecular Docking, and Evaluation Antioxidant and Antimicrobial Activities for Novel 3-Phenylimidazolidin-4-One and 2-Aminothiazol-4-One Derivatives

Abstract

On our way to discovering and developing compounds that have an antioxidant impact compared to ascorbic acid and other biological activities, we designed, synthesized, and evaluated a new series of heterocyclic moieties drugs (1–11) as antioxidants and antimicrobial agents. As starting moieties, these new candidates were derived from two promising heterocyclic compounds, imidazoldin-4-one and thiazol-4-one. Firstly, diphenylimidazol 1 was obtained because of the cyclo condensation one-pot ternary reaction of urea, aniline, and chloroacetic acid under thermal conditions. Out of this starting compound, we could design and create new vital rings such as purine and triazine as in compounds 5 and 6, respectively. Secondly, the start thiazole derivative 7 was obtained from the intermolecular cyclization of thiourea, chloroacetic acid, p-nitobezaldehyde in the presence of sodium acetate. We synthesized various derivatives from this second starting compound 7 by being subjected to different reagents such as aniline, phenylenediamine, phenylhydrazine, and barbituric acid to yield 8, 9, 10, and 11, respectively. Using ascorbic acid as the standard compound, the pharmacological testing for antioxidant activity assessment of the produced derivatives was evaluated against ABTS (2,20-azinobis (3-ethylbenzothiazoline-6-sulfonic acid). Candidate 6 exhibited the best activity as an antioxidant agent compared to ascorbic acid as a reference compound. Moreover, all compounds were evaluated as antimicrobial agents against a series of bacteria and fungi. Among all synthesized compounds, compound 6 achieved high efficiency against two types of fungi and four kinds of bacteria, as Clotrimazole and Ampicillin were used as the reference agents, respectively. All chemical structures of the novel synthesized candidates were unequivocally elucidated and confirmed utilizing spectroscopical and elemental investigations.

Novel NO2 semicarbazone ligand and its metal complexes as VEGFR‐2 inhibitors: Synthesis, spectral characterization, density functional theory calculations, molecular docking, and antimicrobial and antitumor evaluation

“…The modeling was done using Molecular Operating Environment (MOE-2015) software, which offers a unique set of capabilities for modeling protein/ligand interactions. [32,33] The X-ray crystallographic structure of the VEGFR-2 enzyme (PDB ID: 1YWN) was downloaded from the protein data bank. [34,35] Water molecules and ligands not involved in the interaction were removed from the co-crystallized enzyme.…”

Design, synthesis, pharmacological evaluation, and in silico studies of the activity of novel spiro pyrrolo[3,4-d]pyrimidine derivatives

“…56 Consequently, it will be possible to recognize which specic structural modications are required to achieve outstanding efficiency in a simple and low-cost way. [57][58][59][60] Fortunately, our candidates exhibited signicant antiinammatory inhibitory activity. These candidates also exhibited considerable antioxidant activity compared to ascorbic acid.…”

Synthesis, crystal structure, Hirshfeld surface analysis and bioactivity studies of the hydrazones derived from 2-methylsulfonyl-5-nitrobezaldehyde against the breast (MCF-7) and cervical (HeLa) cancer cell lines, and their antioxidant potential.

“…A crystal structure of cytochrome c peroxidase enzyme that previously co-crystalized with ascorbic acid was obtained from the protein data bank (PDB code: 2X08). This enzyme-ligand complex was used before for modelling the 3-phenylimidazolidin-4-one and 2-aminothiazol-4-one derivatives against ascorbic acid as a reference ligand [37]. Molecular docking revealed that these compounds are embedded deeply into the binding pocket of cytochrome c peroxidase to interact with vital hydrophilic residues (Fig.…”