Synthesis of New Phenolic Derivatives of Quinazolin-4(3H)-One as Potential Antioxidant Agents—In Vitro Evaluation and Quantum Studies

Pele, Raluca; Marc, Gabriel; Stana, Anca; Ionuț, Ioana; Nastasă, Cristina; Tiperciuc, Brîndușa; Oniga, Ilioara; Pı̂rnău, Adrian; Vlase, Laurian; Oniga, Ovidiu

doi:10.3390/molecules27082599

Cited by 8 publications

(16 citation statements)

References 40 publications

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“…In addition, the oxidation potential of the hydroxyl group plays an important role in determining the entity responsible for the activity. Čačić et al [43] proved that the catecholic part 2.3dihydroxybenzylidene (phenolic ring carrying two hydroxyl groups in ortho position; adjacent) is crucial for the anti-radical activity, as well as other authors [44][45], who investigated coumarin derivatives with o-dihydroxy phenolic groups. When two hydroxyl groups are at position 2-5 of the phenyl ring, a stable phenoxyl radical is formed, which allows an oxygen atom to share a positive charge, which causes stabilization by delocalization.…”

Section: Hydroxyl Radical Oh• Scavenging Capacitymentioning

confidence: 94%

Effect of Bridging Atom and Hydroxyl Position on the Antioxidant Capacity of Six Phenolic Schiff Bases

et al. 2022

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A series of new phenolic Schiff bases N,N-bis(2,3-dihydroxybenzyl-idene)-4,4’-diphenylmethane (3-DPM), and N,N-bis(2,5-dihydroxybenzylidene)-4,4’-diphenylmethane (5-DPM), for sulfide bridge N,N-bis(2,3-dihydroxybenzyl-idene)-4,4’-diphenyl sulfide (3-DPS), N,N-bis(2,5-dihydroxybenzylidene)-4,4’-diphenyl sulfide (5-DPS), N,N-bis(2,3-dihydroxybenzyl-idene)-4,4’-diphenyl disulfide (3-DPSS), and N,N-bis(2,5-dihydroxybenzylidene)-4,4’-diphenyl disulfide (5-DPSS) were synthesized by condensation of substituted 4,4’-diamino-bis-(4-aminophenyl) methane/sulfide with various substituted aldehydes. The synthesized molecules were characterized by physical data, elemental, IR and 1H-NMR analyses. The antioxidant ability of compounds was determined through the use in vitro assays such as DPPH• scavenging, ABTS, total antioxidant capacity (TAC), hydroxyl radical OH• scavenging, and reducing power capability. The antioxidant activity of the compounds increased slightly after changing the atom bridge and hydroxyl group position. The results showed that the compound 5-DPSS exhibited superior scavenging strength against DPPH (EC50 = 7.10 ± 0.16 μg/mL), whereas 3-DPSS showed the highest activity (EC50 = 1.36 ± 0.08 μg/mL) when inspected by ABTS in relation to butylated hydroxyanisole (BHA) (EC50 = 7.54 ± 0.67). The higher OH• activity was marked by the compound 5-DPS (EC50 = 44.9 ± 3.3 μg/mL) related to BHT at (EC50 = 98.73 ± 0.3 μg/mL). The compounds 5-DPM demonstrated remarkable activity both reducing power (EC50 = 53.2 ± 0.3 μg/mL), and TAC assay (EC50 = 620.0 ± 2.4 μg/mL). These results prove that the modification in hydroxyl group position affect the antioxidant ability of Schiff bases.

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Section: Hydroxyl Radical Oh• Scavenging Capacitymentioning

confidence: 94%

Effect of Bridging Atom and Hydroxyl Position on the Antioxidant Capacity of Six Phenolic Schiff Bases

et al. 2022

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“…In order to evaluate the electron donation capacity of CHT, three assays were carried out: Ferric Reducing Antioxidant Potential (FRAP), Reducing Power (RP) and Phosphomolybdate Assay for Total Antioxidant Capacity (TAC). From the reference compounds and CHT, solutions with a concentration of 0.2 mM in DMSO were obtained by diluting the stock solutions, which were subsequently used according to the protocols that our group previously reported [ 7 , 9 , 17 ]. The absorbance of the resulted mixtures in each assay was determined spectrophotometrically against a blank sample.…”

Section: Methodsmentioning

confidence: 99%

“…In the current research, we proposed to develop a new compound with strong antioxidant activity, based on molecular hybridization, based on combining the most convenient fragments in terms of activity from previous papers reported in the field [ 6 , 7 , 8 , 9 , 10 ], with the resulted compound to have a low bond dissociation enthalpy (BDE) of the phenol O-H bonds.…”

Section: Introductionmentioning

confidence: 99%

Antioxidant Activity Evaluation and Assessment of the Binding Affinity to HSA of a New Catechol Hydrazinyl-Thiazole Derivative

et al. 2022

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Polyphenols have attained pronounced attention due to their ability to provide numerous health benefits and prevent several chronic diseases. In this study, we designed, synthesized and analyzed a water-soluble molecule presenting a good antioxidant activity, namely catechol hydrazinyl-thiazole (CHT). This molecule contains 3′,4′-dihydroxyphenyl and 2-hydrazinyl-4-methyl-thiazole moieties linked through a hydrazone group with very good antioxidant activity in the in vitro evaluations performed. A preliminary validation of the CHT developing hypothesis was performed evaluating in silico the bond dissociation enthalpy (BDE) of the phenol O-H bonds, compared to our previous findings in the compounds previously reported by our group. In this paper, we report the binding mechanism of CHT to human serum albumin (HSA) using biophysical methods in combination with computational studies. ITC experiments reveal that the dominant forces in the binding mechanism are involved in the hydrogen bond or van der Waals interactions and that the binding was an enthalpy-driven process. NMR relaxation measurements were applied to study the CHT–protein interaction by changing the drug concentration in the solution. A molecular docking study added an additional insight to the experimental ITC and NMR analysis regarding the binding conformation of CHT to HSA.

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“…Recently, novel hybrid compounds of quinazolin‐4‐one and phenol scaffolds (Mekheimer et al, 2022) were discovered (Pele et al, 2022). Their antioxidant capacity was tested in vitro.…”

Section: Biological Actionsmentioning

confidence: 99%

A comprehensive review of recent advances in the biological activities of quinazolines

Gomaa

2022

Chem Biol Drug Des

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Quinazoline heterocycles are critical in the development of medications.Quinazoline derivatives have been intensively researched, providing a wide range of compounds with diverse biological roles. The quinazoline nucleus has garnered a lot of attention in medical chemistry in recent years. It was assumed to be a pharmacophore component in the development of physiologically interesting drugs. This review is an attempt to increase the potential of quinazoline by highlighting a wide range of advancements demonstrated by numerous derivatives of the quinazoline moiety, as well as focusing on diverse pharmacological actions of the quinazoline moiety. This review compiles recent studies on the quinazoline moiety described in the literature by researchers.

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Synthesis of New Phenolic Derivatives of Quinazolin-4(3H)-One as Potential Antioxidant Agents—In Vitro Evaluation and Quantum Studies

Cited by 8 publications

References 40 publications

Effect of Bridging Atom and Hydroxyl Position on the Antioxidant Capacity of Six Phenolic Schiff Bases

Effect of Bridging Atom and Hydroxyl Position on the Antioxidant Capacity of Six Phenolic Schiff Bases

Antioxidant Activity Evaluation and Assessment of the Binding Affinity to HSA of a New Catechol Hydrazinyl-Thiazole Derivative

A comprehensive review of recent advances in the biological activities of quinazolines

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