An effective strategy to develop active cinnamic acid-directed antioxidants based on elongating the conjugated chains

Area of Science:

• Medicinal Chemistry
• Organic Chemistry
• Biochemistry

Background:

• Cinnamic acid derivatives (CAs) are known for their antioxidant properties.
• Optimizing antioxidant activity and lipophilicity is crucial for developing effective therapeutic agents.

Purpose of the Study:

• To design and synthesize novel CAs with enhanced antioxidant activity and lipophilicity.
• To investigate the impact of conjugated chain elongation on the antioxidant performance of CAs.

Main Methods:

• Synthesis of four CA analogs using a conjugated chain elongation strategy.
• Evaluation of antioxidant activity through DPPH-scavenging, ferric reducing/antioxidant power, cyclic voltammetry, DNA strand breakage inhibition, and anti-haemolysis assays.

Main Results:

• Elongated CAs demonstrated superior DPPH-scavenging, DNA strand breakage-inhibiting, and anti-haemolysis activities compared to parent compounds.
• Improved hydrogen atom-donating ability and lipophilicity were identified as key factors for enhanced antioxidant performance.
• The conjugated chain elongation strategy proved effective in optimizing CA properties.

Conclusions:

• Conjugated chain elongation is an effective strategy for developing potent CA-based antioxidants.
• The synthesized CA analogs show promise as potential therapeutic agents for conditions associated with oxidative stress.