Synthesis of stable aromatic and heteroaromatic sulfonyl-amidoximes and evaluation of their antioxidant and lipid peroxidation activity

Ismini Doulou; Christos Kontogiorgis; Alexandros E Koumbis; Eleni Evgenidou; Dimitra Hadjipavlou-Litina; Konstantina C Fylaktakidou

doi:10.1016/j.ejmech.2014.04.040

Synthesis of stable aromatic and heteroaromatic sulfonyl-amidoximes and evaluation of their antioxidant and lipid peroxidation activity

Eur J Med Chem. 2014 Jun 10:80:145-53. doi: 10.1016/j.ejmech.2014.04.040. Epub 2014 Apr 13.

Authors

Ismini Doulou¹, Christos Kontogiorgis², Alexandros E Koumbis³, Eleni Evgenidou³, Dimitra Hadjipavlou-Litina², Konstantina C Fylaktakidou⁴

Affiliations

¹ Laboratory of Organic, Bioorganic and Natural Products Chemistry, Molecular Biology and Genetics Department, Democritus University of Thrace, 68100 Alexandroupolis, Greece.
² Department of Pharmaceutical Chemistry, School of Pharmacy, Faculty of Health Sciences, Aristotle University of Thessaloniki, 54124 Thessaloniki, Greece.
³ Laboratory of Organic Chemistry, Department of Chemistry, Aristotle University of Thessaloniki, 54124 Thessaloniki, Greece.
⁴ Laboratory of Organic, Bioorganic and Natural Products Chemistry, Molecular Biology and Genetics Department, Democritus University of Thrace, 68100 Alexandroupolis, Greece. Electronic address: kfylakta@mbg.duth.gr.

PMID: 24769352
DOI: 10.1016/j.ejmech.2014.04.040

Abstract

We describe herein the synthesis of stable aromatic and heteroaromatic sulfonyl-amidoximes, from the reaction of amidoximes with the corresponding sulfonyl chlorides, in low to excellent yields. Evaluation of their antioxidant activity has shown that 17 out of 28 compounds highly compete DMSO for hydroxyl radicals, while five of them inhibit lipid peroxidation. Combining the reducing and anti-lipid peroxidation ability it seems that compounds 13 and 31 could be used as lead molecules.

Keywords: Amidoximes; Antioxidant; Hydroxyl radicals; Lipid peroxidation; Sulfonyl-amidoximes.

MeSH terms

Biphenyl Compounds / chemistry
Chemistry Techniques, Synthetic
Drug Design*
Drug Stability
Hydroxyl Radical / chemistry
Lipid Peroxidation / drug effects*
Oximes / chemical synthesis*
Oximes / chemistry
Oximes / pharmacology*
Picrates / chemistry
Structure-Activity Relationship

Substances

Biphenyl Compounds
Oximes
Picrates
Hydroxyl Radical
1,1-diphenyl-2-picrylhydrazyl