Coumarin–Chalcone Hybrids as Peroxyl Radical Scavengers: Kinetics and Mechanisms

Mazzone, Gloria; Galano, Annia; Álvarez-Idaboy, J. Raúl; Russo, Nino

doi:10.1021/acs.jcim.6b00006

Cited by 44 publications

(19 citation statements)

References 113 publications

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“…Biological properties for phenols and their derivatives have been broadly studied, revealing many of their desirable biological properties. One of these properties is their outstanding antioxidant capacity …”

Section: Resultsmentioning

confidence: 99%

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Thiophenols, Promising Scavengers of Peroxyl Radicals: Mechanisms and kinetics

2019

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The activity of 12 thiophenols as primary antioxidants in aqueous solution has been studied using density functional theory. Twelve different substituted thiophenols were tested as peroxyl radicals scavengers. Single electron transfer (SET) and formal hydrogen transfer (FHT) were investigated. The SET mechanism was found to be the main mechanism, with rate constants that are close to the diffusion limit, which means that these thiophenolic compounds have the capacity to scavenge peroxyl radicals before they can damage biomolecules. All 12 thiophenolic compounds react faster with methylperoxyl than with hydroperoxyl radicals. In addition, it was found that pH plays an important role in the reactivity of these compounds. © 2019 Wiley Periodicals, Inc.

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Section: Resultsmentioning

confidence: 99%

“…One of these properties is their outstanding antioxidant capacity. [75][76][77][78][79][80][81] The oxygen analog of specie A is phenol. As a HOO • scavenger, phenol is seen to be less efficient than thiophenol, in fact, its reaction rate constant is 28.3 times smaller.…”

Section: Scavenging Of Hydroperoxyl Radicalsmentioning

confidence: 99%

Thiophenols, Promising Scavengers of Peroxyl Radicals: Mechanisms and kinetics

2019

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“…Another study provided more evidence on the radical-scavenging property of the hybrids. 330 Chalcone–coumarin derivatives also possess antitumor activity that significantly inhibited in vitro and in vivo tumor growth. 325,326 Compound 88 has been reported to show antibacterial activity for the treatment of tenacibaculosis in fish.…”

Section: Medicinal Aspects Of Chalconesmentioning

confidence: 99%

Chalcone: A Privileged Structure in Medicinal Chemistry

et al. 2017

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Privileged structures have been widely used as an effective template in medicinal chemistry for drug discovery. Chalcone is a common simple scaffold found in many naturally occurring compounds. Many chalcone derivatives have also been prepared due to their convenient synthesis. These natural products and synthetic compounds have shown numerous interesting biological activities with clinical potentials against various diseases. This review aims to highlight the recent evidence of chalcone as a privileged scaffold in medicinal chemistry. Multiple aspects of chalcone will be summarized herein, including the isolation of novel chalcone derivatives, the development of new synthetic methodologies, the evaluation of their biological properties, and the exploration of the mechanisms of action as well as target identification. This review is expected to be a comprehensive, authoritative, and critical review of the chalcone template to the chemistry community.

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“…In these reactions a newly formed radical, which is more stable and less reactive than the previous one, is generated. There are several mechanisms of the antioxidant actions of free radicals: hydrogen atom transfer (HAT), proton coupled electron Transfer (PCET), single electron transfer followed by proton transfer (SET-PT), sequential proton loss electron transfer (SPLET), radical adduct formation (RAF), and sequential proton loss hydrogen atom transfer (SPLHAT) (Klein et al 2007;Litwinienko and Ingold 2007;Galano 2015;Galano et al 2016;Mazzone et al 2016). …”

Section: The Antioxidant Mechanismsmentioning

confidence: 99%

Study of the mechanisms of antioxidative action of different antioxidants

Marković¹

2016

J Serb Soc Comp Mech

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The reaction mechanisms by which antioxidants can exert their activity are: hydrogen atom transfer (HAT), proton coupled electron transfer (PCET), sequential proton loss electron transfer (SPLET), single electron transfer -proton transfer (SET-PT), radical adduct formation, and sequential proton loss hydrogen atom transfer. The antioxidative activity of different compounds (flavones, flavonols, and Schiff basis) was investigated by the trolox equivalent antioxidative capacity and electron paramagnetic resonance methods. The mechanisms of the antioxidative action (HAT, PCET, SPLET, and SET-PT) were investigated by using the thermodynamic parameters: bond dissociation enthalpy, ionization potential, proton dissociation enthalpy, proton affinity, and electron-transfer enthalpy. The influence of different radicals was investigated using appropriate isodesmic reactions. The mechanistic approach to the investigation of the influence of different radicals to the HAT mechanism, and the second step of the SET-PT mechanism) was applied. These investigations contribute to the elucidation and understanding of complex processes involved in the antioxidative action.

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Coumarin–Chalcone Hybrids as Peroxyl Radical Scavengers: Kinetics and Mechanisms

Cited by 44 publications

References 113 publications

Thiophenols, Promising Scavengers of Peroxyl Radicals: Mechanisms and kinetics

Thiophenols, Promising Scavengers of Peroxyl Radicals: Mechanisms and kinetics

Chalcone: A Privileged Structure in Medicinal Chemistry

Study of the mechanisms of antioxidative action of different antioxidants

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