title: The first synthesis of 4-phenylbutenone derivative bromophenols including natural products and their inhibition profiles for carbonic anhydrase, acetylcholinesterase and butyrylcholinesterase enzymes.
abstract: The first synthesis of (E)-4-(3-bromo-4,5-dihydroxyphenyl)but-3-en-2-one (1), (E)-4-(2-bromo-4,5-dihydroxyphenyl)but-3-en-2-one (2), and (E)-4-(2,3-dibromo-4,5-dihydroxyphenyl)but-3-en-2-one (3) was realized as natural bromophenols. Derivatives with mono OMe of 2 and 3 were obtained from the reactions of their derivatives with di OMe with AlCl3. These novel 4-phenylbutenone derivatives were effective inhibitors of the cytosolic carbonic anhydrase I and II isoenzymes (hCA I and II), acetylcholinesterase (AChE) and butyrylcholinesterase (BChE) with Kivalues in the range of 158.07-404.16pM for hCA I, 107.63-237.40pM for hCA II, 14.81-33.99pM for AChE and 5.64-19.30pM for BChE. The inhibitory effects of the synthesized novel 4-phenylbutenone derivatives were compared to acetazolamide as a clinical hCA I and II isoenzymes inhibitor and tacrine as a clinical AChE and BChE enzymes inhibitor.
authors.affiliation: Department of Chemistry, Faculty of Science, Atatürk University, 25240 Erzurum, Turkey.
authors.forename: Çetin
authors.initials: Ç
authors.lastname: Bayrak
authors.affiliation: Department of Chemistry, Faculty of Science, Atatürk University, 25240 Erzurum, Turkey.
authors.forename: Parham
authors.initials: P
authors.lastname: Taslimi
authors.affiliation: Department of Chemistry, Faculty of Science, Atatürk University, 25240 Erzurum, Turkey.
authors.forename: İlhami
authors.initials: İ
authors.lastname: Gülçin
authors.affiliation: Department of Chemistry, Faculty of Science, Atatürk University, 25240 Erzurum, Turkey. Electronic address: amenzek@atauni.edu.tr.
authors.forename: Abdullah
authors.initials: A
authors.lastname: Menzek
mesh_terms: D000110:Acetylcholinesterase / Q000378:metabolism; D001688:Biological Products / Q000138:chemical synthesis / Q000737:chemistry / Q000494:pharmacology*; D002074:Butanones / Q000138:chemical synthesis / Q000737:chemistry / Q000494:pharmacology*; D002091:Butyrylcholinesterase / Q000378:metabolism; D024401:Carbonic Anhydrase I / Q000037:antagonists & inhibitors / Q000378:metabolism; D024402:Carbonic Anhydrase II / Q000037:antagonists & inhibitors / Q000378:metabolism; D002257:Carbonic Anhydrase Inhibitors / Q000138:chemical synthesis / Q000737:chemistry / Q000494:pharmacology*; D002800:Cholinesterase Inhibitors / Q000138:chemical synthesis / Q000737:chemistry / Q000494:pharmacology*; D004305:Dose-Response Relationship, Drug; D006801:Humans; D015394:Molecular Structure; D010636:Phenols / Q000138:chemical synthesis / Q000737:chemistry / Q000494:pharmacology*; D013329:Structure-Activity Relationship
chemical_list: D001688:Biological Products; D002074:Butanones; D002257:Carbonic Anhydrase Inhibitors; D002800:Cholinesterase Inhibitors; D010636:Phenols; C025383:benzylideneacetone; D000110:Acetylcholinesterase; D002091:Butyrylcholinesterase; D024401:Carbonic Anhydrase I; D024402:Carbonic Anhydrase II
keywords: Acetylcholinesterase; Bromination; Bromophenols; Butyrylcholinesterase; Carbonic anhydrase; Enzyme inhibition; Natural products; Phenylbutenone