Monoterpenoid selenophenes derived from (-)-carvone with GPx-like activity

Area of Science:

• Medicinal Chemistry
• Organic Synthesis
• Pharmacology

Background:

• Organoselenium compounds show therapeutic promise for various diseases.
• Integrating selenium into natural products can enhance biological effects.
• Natural monoterpenoids are valuable scaffolds for drug discovery.

Purpose of the Study:

• To synthesize novel organoselenium compounds from (-)-carvone.
• To evaluate the antioxidant and glutathione peroxidase (GPx)-like activity of synthesized compounds.
• To explore structure-activity relationships of these selenium derivatives.

Main Methods:

• One-pot synthesis of mentoselenophenone 1 from (-)-carvone and selenium bromide.
• Preparation of derivatives: α,α dimer 6, oxime 7, and lactam 8.
• Assessment of antioxidant activity using GPx-like assays.

Main Results:

• Mentoselenophenone 1 and phenols 2, 3 were synthesized.
• Derivatives α,α dimer 6, oxime 7, and lactam 8 were prepared.
• Compounds 1, 2, 6, and 7 demonstrated significant GPx-like antioxidant activity, with dimer 6 being the most potent.

Conclusions:

• Novel organoselenium compounds were successfully synthesized from (-)-carvone.
• The synthesized compounds, especially dimer 6, possess notable antioxidant properties.
• These findings highlight the potential of these selenium derivatives as therapeutic agents.