title: Synthesis, antioxidant, and antiacetylcholinesterase activities of sulfonamide derivatives of dopamine-related compounds.
abstract: A series of sulfonamides were synthesized from dopamine derivatives. The reactions of amines with methanesulfonyl chloride followed by O-demethylation with BBr3 afforded phenolic sulfonamides. The antioxidant activities of the synthesized phenolic sulfonamides were investigated by thiocyanate method, 2,2'-azino-bis(3-ethylbenzthiazoline-6-sulfonic acid) (ABTS(•+)), 1,1-diphenyl-2-picryl-hydrazyl (DPPH(•)), N,N-dimethyl-p-phenylenediamine (DMPD(•+)), and superoxide anion (O2(•-)) radical scavenging, reducing power, and ferrous ion (Fe(2+)) chelating assays. Sulfonamides 13-16 showed around 75-85% inhibition on linoleic acid peroxidation. On the other hand, butylated hydroxyanisole (BHA), butylated hydroxytoluene (BHT), α-tocopherol, and trolox indicated an inhibition of 90.0%, 85.73%, 73.33%, and 85.73% on peroxidation, respectively, in the same system at the same concentration (10 µg/mL). Also, the inhibition effects of the synthesized compounds on acetylcholinesterase (AChE) activity were evaluated. AChE was effectively inhibited by sulfanomides 13-16, with K(i) values in the range of 33.04 ± 4.3 to 131.68 ± 8.8 nM.
authors.affiliation: Central Researching Laboratory, Agri Ibrahim Cecen University, Agri, Turkey; Faculty of Science, Department of Chemistry, Atatürk University, Erzurum, Turkey.
authors.forename: Hülya
authors.initials: H
authors.lastname: Göçer
authors.forename: Akın
authors.initials: A
authors.lastname: Akıncıoğlu
authors.forename: Necla
authors.initials: N
authors.lastname: Öztaşkın
authors.forename: Süleyman
authors.initials: S
authors.lastname: Göksu
authors.forename: İlhami
authors.initials: İ
authors.lastname: Gülçin
mesh_terms: D000110:Acetylcholinesterase / Q000378:metabolism; D000544:Alzheimer Disease / Q000188:drug therapy / Q000201:enzymology; D000975:Antioxidants / Q000138:chemical synthesis* / Q000494:pharmacology*; D002800:Cholinesterase Inhibitors / Q000138:chemical synthesis* / Q000494:pharmacology*; D004298:Dopamine / Q000031:analogs & derivatives / Q000138:chemical synthesis* / Q000494:pharmacology*; D016166:Free Radical Scavengers / Q000138:chemical synthesis / Q000494:pharmacology; D058851:GPI-Linked Proteins / Q000037:antagonists & inhibitors / Q000378:metabolism; D006801:Humans; D015227:Lipid Peroxidation / Q000187:drug effects; D015394:Molecular Structure; D013449:Sulfonamides / Q000138:chemical synthesis* / Q000494:pharmacology*
chemical_list: D000975:Antioxidants; D002800:Cholinesterase Inhibitors; D016166:Free Radical Scavengers; D058851:GPI-Linked Proteins; D013449:Sulfonamides; C548244:ACHE protein, human; D000110:Acetylcholinesterase; D004298:Dopamine
keywords: Antiacetylcholinesterase activity; Antioxidant activity; Dopamine; Phenolic compound; Radical scavenging; Sulfonamides