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Free Radicals in Chemical Biology: from Chemical Behavior to Biomarker Development
Published on: April 15, 2013
Synthesis and effect on free radical processes on some substituted morpholine derivatives with potential biologic
E Tani1, E Rekka, P N Kourounakis
1Department of Pharmaceutical Chemistry, School of Pharmacy, University of Thessaloniki, Greece.
Arzneimittel-Forschung
|September 1, 1994
Summary
New morpholine derivatives show potent antioxidant activity, protecting against lipid peroxidation and hydroxyl radical oxidation. Lipophilicity did not significantly influence their effectiveness in these antioxidant processes.
Area of Science:
- Medicinal Chemistry
- Pharmacology
- Free Radical Chemistry
Background:
- Morpholine derivatives exhibit antioxidant and biological activities, suggesting involvement in free radical processes.
- Previous research indicates potential for developing novel antioxidants from this chemical class.
Purpose of the Study:
- To synthesize novel 2-hydroxy(alkoxy)-2-biphenyl-4-methyl-morpholine derivatives.
- To evaluate the antioxidant potential of these synthesized compounds.
- To investigate the relationship between lipophilicity and antioxidant activity.
Main Methods:
- Synthesis of 2-hydroxy-2-biphenyl-4-methyl-morpholine via reaction of N-methyl-ethanolamine and p-phenyl-phenacylbromide.
- Formation of 2-alkoxy-2-biphenyl-4-methyl morpholines through acid-catalyzed ketal formation.
- Assessment of lipophilicity using reversed-phase thin-layer chromatography (TLC) (RM values).
- Evaluation of antioxidant activity against hepatic microsomal lipid peroxidation and hydroxyl radical-mediated oxidation of dimethylsulfoxide.
Main Results:
- The synthesized 2-biphenyl substituted morpholines demonstrated potent antioxidant activity.
- Antioxidant efficacy was observed in both lipid peroxidation and hydroxyl radical scavenging assays.
- Lipophilicity, measured by RM values, was not found to be a critical factor determining the antioxidant properties of these compounds.
Conclusions:
- The novel synthesized morpholine derivatives possess significant antioxidant capabilities.
- A potential mechanism underlying their antioxidant properties was proposed.
- Lipophilicity is not a primary determinant of the antioxidant activity in these specific biphenyl-substituted morpholines.
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