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

• Published in: European journal of medicinal chemistry Vol. 80; pp. 145 - 153
• Main Authors: Doulou, Ismini, Kontogiorgis, Christos, Koumbis, Alexandros E., Evgenidou, Eleni, Hadjipavlou-Litina, Dimitra, Fylaktakidou, Konstantina C.
• Format: Journal Article
• Language: English
• Published: PARIS Elsevier Masson SAS 10.06.2014; Elsevier
• Subjects: Amidoximes; Antioxidant; Biphenyl Compounds - chemistry; Chemistry Techniques, Synthetic; Chemistry, Medicinal; Drug Design; Drug Stability; Hydroxyl Radical - chemistry; Hydroxyl radicals; Life Sciences & Biomedicine; Lipid peroxidation; Lipid Peroxidation - drug effects; Oximes - chemical synthesis; Oximes - chemistry; Oximes - pharmacology; Pharmacology & Pharmacy; Picrates - chemistry; Science & Technology; Structure-Activity Relationship; Sulfonyl-amidoximes; Hydroxyl radicals; Lipid peroxidation; Amidoximes; Antioxidant; Sulfonyl-amidoximes; TRANSFORMATION; ANTIINFLAMMATORY ACTIVITY; DESIGN; OXIDE; REARRANGEMENT; BIOLOGICAL EVALUATION; CHEMISTRY; AGENTS; INHIBITORS; COUMARIN DERIVATIVES
• ISSN: 0223-5234; 1768-3254
• DOI: 10.1016/j.ejmech.2014.04.040

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. [Display omitted] •Synthesis of series of stable aromatic and heteroaromatic sulfonyl amidoximes.•Biological evaluation of sulfonyl amidoximes, realized for the first time.•The majority of compounds exhibited inhibition of free hydroxyl radicals.•Some exhibited lipid peroxidation activity.