Synthesis of stable aromatic and heteroaromatic sulfonyl-amidoximes and evaluation of their antioxidant and lipid peroxidation activity.
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.
Laboratory of Organic, Bioorganic and Natural Products Chemistry, Molecular Biology and Genetics Department, Democritus University of Thrace, 68100 Alexandroupolis, Greece.
Ismini
I
Doulou
Department of Pharmaceutical Chemistry, School of Pharmacy, Faculty of Health Sciences, Aristotle University of Thessaloniki, 54124 Thessaloniki, Greece.
Christos
C
Kontogiorgis
Laboratory of Organic Chemistry, Department of Chemistry, Aristotle University of Thessaloniki, 54124 Thessaloniki, Greece.
Alexandros E
AE
Koumbis
Laboratory of Organic Chemistry, Department of Chemistry, Aristotle University of Thessaloniki, 54124 Thessaloniki, Greece.
Eleni
E
Evgenidou
Department of Pharmaceutical Chemistry, School of Pharmacy, Faculty of Health Sciences, Aristotle University of Thessaloniki, 54124 Thessaloniki, Greece.
Dimitra
D
Hadjipavlou-Litina
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.
Konstantina C
KC
Fylaktakidou
D001713:Biphenyl Compounds / Q000737:chemistry; D060326:Chemistry Techniques, Synthetic; D015195:Drug Design; D004355:Drug Stability; D017665:Hydroxyl Radical / Q000737:chemistry; D015227:Lipid Peroxidation / Q000187:drug effects*; D010091:Oximes / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology*; D010851:Picrates / Q000737:chemistry; D013329:Structure-Activity Relationship
D001713:Biphenyl Compounds; D010091:Oximes; D010851:Picrates; D017665:Hydroxyl Radical; C004931:1,1-diphenyl-2-picrylhydrazyl
Amidoximes; Antioxidant; Hydroxyl radicals; Lipid peroxidation; Sulfonyl-amidoximes