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A Structure-Activity Relationship Study on the Antioxidant Properties of Dithiocarbamic Flavanones
Mihail Lucian Birsa1, Laura Gabriela Sarbu1
1Department of Chemistry, Alexandru Ioan Cuza University of Iasi, No. 11 Carol I Boulevard, 700506 Iasi, Romania.
Antioxidants (Basel, Switzerland)
|August 29, 2024
Summary
Halogenated dithiocarbamic flavanones show potent antioxidant activity. Specifically, C-8 halogen substituents enhance free radical scavenging, outperforming BHT and ascorbic acid.
Area of Science:
- Medicinal Chemistry
- Organic Chemistry
- Pharmacology
Background:
- Flavanones are a class of flavonoids with diverse biological activities.
- Dithiocarbamate derivatives are known for their potential therapeutic applications.
- Understanding structure-activity relationships is crucial for developing novel antioxidants.
Purpose of the Study:
- To investigate the antioxidant properties of novel 3-dithiocarbamic flavanones.
- To evaluate the influence of halogen substituents on Ring A and the dithiocarbamic moiety.
- To compare the efficacy of these compounds against standard antioxidants like BHT and ascorbic acid.
Main Methods:
- Synthesis of 3-dithiocarbamic flavanone derivatives.
- Evaluation of antioxidant activity using DPPH and ABTS assays.
- Computational analysis to understand radical intermediate stability.
Main Results:
- Compounds with a halogen substituent at the C-8 position exhibited superior antioxidant activity.
- These derivatives showed better performance than butylated hydroxytoluene (BHT) and ascorbic acid.
- Halogenation at C-8 stabilized a free radical intermediate at the C-3 position.
Conclusions:
- The C-8 halogen substituent significantly enhances the antioxidant capacity of dithiocarbamic flavanones.
- A stable free radical enolate intermediate is likely responsible for the observed antioxidant activity.
- Dithiocarbamic moiety plays a key role in the antioxidant properties of these flavanones.
