Acetylcholinesterase inhibitory and antioxidant activities of novel symmetric sulfamides derived from phenethylamines.
The antioxidant and acetylcholinesterase inhibitory properties of novel symmetric sulfamides derived from phenethylamines were evaluated. Phenethylamines 8-11 were reacted with SO2Cl2 in the presence of Et3N to afford sulfamides in good yields. The synthesized sulfamides were converted to their phenolic derivatives with BBr3. We elucidated the antioxidant activity of novel symmetric sulfamides by using different bioanalytical assays. For this purpose, the radical scavenging activities of the novel symmetric sulfamides were assessed by DPPH(•), ABTS(•+), DMPD(•+), and O2(•-) radical scavenging tests. In addition, the reducing abilities of the novel symmetric sulfamides were evaluated by Fe(3+)-Fe(2+) reducing, Cu(2+)-Cu(+) reducing, and [Fe(3+)-(TPTZ)2](3+)-[Fe(2+)-(TPTZ)2](2+) reducing activity tests. Also, the Fe(2+) chelating activity by the pipyrdyl reagent and the acetylcholinesterase inhibitory activities of the novel symmetric sulfamides were studied. Especially, the novel phenolic and symmetric sulfamides 16-19 showed high antioxidant and acetylcholinesterase inhibitory properties. On the other hand, IC50 values were calculated for the DPPH(•), ABTS(•+), DMPD(•+), and O2(•-) scavenging, the metal chelating, and the acetylcholinesterase inhibition effects of the novel symmetric sulfamides.
Department of Chemistry, Faculty of Science, Ataturk University, Erzurum, Turkey.
Kadir
K
Aksu
Department of Chemistry, Faculty of Science, Ataturk University, Erzurum, Turkey.
Fevzi
F
Topal
Department of Chemistry, Faculty of Science, Ataturk University, Erzurum, Turkey.|Fetal Programming of Diseases Research Chair, Zoology Department, College of Science, King Saud University, Riyadh, Saudi Arabia.
İlhami
İ
Gulcin
Department of Chemistry, Faculty of Science and Arts, Sutcu Imam University, Kahramanmaras, Turkey.
Ferhan
F
Tümer
Department of Chemistry, Faculty of Science, Ataturk University, Erzurum, Turkey.
Süleyman
S
Göksu
D000110:Acetylcholinesterase / Q000378:metabolism*; D000975:Antioxidants / Q000138:chemical synthesis* / Q000494:pharmacology*; D002800:Cholinesterase Inhibitors / Q000138:chemical synthesis* / Q000494:pharmacology*; D015195:Drug Design; D005609:Free Radicals / Q000737:chemistry; D007502:Iron Chelating Agents / Q000138:chemical synthesis / Q000494:pharmacology; D015394:Molecular Structure; D010084:Oxidation-Reduction; D010627:Phenethylamines / Q000737:chemistry*; D017382:Reactive Oxygen Species / Q000737:chemistry; D013329:Structure-Activity Relationship; D013449:Sulfonamides / Q000138:chemical synthesis* / Q000494:pharmacology*
D000975:Antioxidants; D002800:Cholinesterase Inhibitors; D005609:Free Radicals; D007502:Iron Chelating Agents; D010627:Phenethylamines; D017382:Reactive Oxygen Species; D013449:Sulfonamides; D000110:Acetylcholinesterase
Acetylcholine esterase; Antioxidant activity; Enzyme inhibition; Phenethylamines; Sulfamide