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Related Concept Videos

Radical Reactivity: Overview01:11

Radical Reactivity: Overview

Radicals, the highly reactive species, gain stability by undergoing three different reactions. The first reaction involves a radical-radical coupling, in which a radical combines with another radical, forming a spin‐paired molecule. The second reaction is between a radical and a spin‐paired molecule, generating a new radical and a new spin‐paired molecule. The third reaction is radical decomposition in a unimolecular reaction, forming a new radical and a spin‐paired molecule. These three...
Radical Reactivity: Steric Effects01:10

Radical Reactivity: Steric Effects

The presence of electron-donating, electron-withdrawing, or conjugating groups adjacent to a radical center, imparts electronic stabilization to the radicals. Examples of such electronically-stabilized radicals are triphenylmethyl, tetramethylpiperidine‐N‐oxide, and 2,2‐diphenyl‐1‐picrylhydrazyl. These radicals are remarkably stable and are known as persistent radicals. Some of the persistent radicals can even be isolated and purified.
Along with electronic factors, steric factors also account...
Radical Reactivity: Nucleophilic Radicals01:16

Radical Reactivity: Nucleophilic Radicals

Radicals adjacent to electron-donating groups are called nucleophilic radicals. These radicals readily react with electrophilic alkenes. The SOMO–LUMO interactions are the driving force for the reaction, where the high-energy SOMO of the electron-rich, nucleophilic radicals interacts with the low-energy LUMO of the electron-deficient, electrophilic alkenes. Such SOMO–LUMO interactions are the basis of reactive radical traps, affecting the selectivity in radical reactions. For instance, consider...
Radical Formation: Overview01:03

Radical Formation: Overview

A bond can be broken either by heterolytic bond cleavage to form ions or homolytic bond cleavage to yield radicals. A fishhook arrow is used to represent the motion of a single electron in homolytic bond cleavage. There are two main sources from which radicals can be formed:
Radicals from spin-paired molecules:
Radicals can be obtained from spin-paired molecules either by homolysis or electron transfer. While two radicals are formed in the former, an electron is added in the latter, also known...
Radical Formation: Elimination00:51

Radical Formation: Elimination

Another method of radical formation is the elimination process. It is the opposite of the addition route and is driven by the instability of the radical. For example, as depicted in Figure 1, dibenzoyl peroxide yields a pair of unstable radicals upon homolysis. Given its instability, this radical spontaneously undergoes elimination via a C–C bond cleavage to form a relatively more stable phenyl radical. The mechanism involves cleavage of the bond between the α and β positions with respect to...
Radical Reactivity: Intramolecular vs Intermolecular01:33

Radical Reactivity: Intramolecular vs Intermolecular

Radical reactions can occur either intermolecularly or intramolecularly. In an intermolecular radical reaction, a nucleophilic radical adds to an electrophilic alkene or vice versa. In such reactions, the radical and generally the alkene, which is also called the radical trap, are two different molecules. Additionally, for such intermolecular reactions to occur, the radical trap must be active, present in an excess concentration, and the radical starting material must have a weak carbon–halogen...

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Free Radicals in Chemical Biology: from Chemical Behavior to Biomarker Development
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Free Radicals in Chemical Biology: from Chemical Behavior to Biomarker Development

Published on: April 15, 2013

Topological sub-structural molecular design approach: radical scavenging activity.

Alfonso Pérez-Garrido1, Aliuska Morales Helguera, Juana M Morillas Ruiz

  • 1Cátedra de Ingeniería y Toxicología Ambiental, Universidad Católica San Antonio, Guadalupe, Murcia, Spain. Aperez@pdi.ucam.edu

European Journal of Medicinal Chemistry
|January 17, 2012
PubMed
Summary

This study developed a novel Quantitative Structure-Activity Relationship (QSAR) model using TOPS-MODE descriptors to predict antioxidant activity across diverse phenolic compounds. The model accurately unifies various antioxidant families, highlighting hydrogen bonding and polarity as key factors.

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Area of Science:

  • Medicinal Chemistry
  • Computational Chemistry
  • Pharmacology

Background:

  • Phenolic compounds exhibit beneficial health effects, including anti-inflammatory, anticancer, and antiviral activities, primarily due to their antioxidant properties.
  • The antioxidant activity of phenolics is linked to their chemical structure, with previous Structure-Activity Relationship (SAR) and Quantitative Structure-Activity Relationship (QSAR) models focusing on specific chemical families.
  • Existing models are limited in scope, often not applicable to diverse groups of antioxidant substances.

Purpose of the Study:

  • To develop a unified QSAR model for a heterogeneous group of phenolic compounds to predict antioxidant activity.
  • To interpret antioxidant activity using bond contributions derived from TOPS-MODE descriptors.
  • To identify key structural features driving radical scavenging activity in a broad range of compounds.

Main Methods:

  • Development of a QSAR model utilizing TOPS-MODE descriptors for a diverse set of phenolic compounds.
  • Analysis of bond contributions to understand the structural basis of antioxidant activity.
  • Validation of the model for predictive ability and stability.

Main Results:

  • The developed QSAR model explains over 90% of the variance in experimental antioxidant activity.
  • The model demonstrates good predictive capability and stability across different chemical families.
  • Key drivers for radical scavenging activity identified as hydrogen bond donation and polarity.

Conclusions:

  • A unified QSAR model has been successfully created for diverse phenolic antioxidants, overcoming limitations of previous family-specific models.
  • The model provides a robust tool for predicting the radical scavenging activity of novel substances.
  • Understanding the roles of hydrogen bonding and polarity offers insights for designing new antioxidants.