title: Synthesis of 4,5-disubstituted-2-thioxo-1,2,3,4-tetrahydropyrimidines and investigation of their acetylcholinesterase, butyrylcholinesterase, carbonic anhydrase I/II inhibitory and antioxidant activities.
abstract: A series of tetrahydropyrimidinethiones were synthesized from thiourea, β-diketones and aromatic aldehydes, such as p-tolualdehyde, p-anisaldehyde, o-tolualdehyde, salicylaldehyde and benzaldehyde. These cyclic thioureas showed good inhibitory action against acetylcholine esterase (AChE), butyrylcholine esterase (BChE), and human (h) carbonic anhydrase (CA) isoforms I and II. AChE and BChE inhibitions were in the range of 6.11-16.13 and 6.76-15.68 nM, respectively. hCA I and II were effectively inhibited by these compounds, with Kivalues in the range of 47.40-76.06 nM for hCA I, and of 30.63-76.06 nM for hCA II, respectively. The antioxidant activity of the cyclic thioureas was investigated by using different in vitro antioxidant assays, including 1,1-diphenyl-2-picrylhydrazyl (DPPH·) radical scavenging, Cu2+and Fe3+reducing, and Fe2+chelating activities.
authors.affiliation: a Laboratory of Theoretical Bases of Synthesis and Action Mechanism of Additives , Institute of Chemistry of Additives, Azerbaijan National Academy of Sciences , Baku , Azerbaijan.
authors.forename: Emin
authors.initials: E
authors.lastname: Garibov
authors.affiliation: b Department of Chemistry , Faculty of Sciences, Ataturk University , Erzurum , Turkey.
authors.forename: Parham
authors.initials: P
authors.lastname: Taslimi
authors.affiliation: a Laboratory of Theoretical Bases of Synthesis and Action Mechanism of Additives , Institute of Chemistry of Additives, Azerbaijan National Academy of Sciences , Baku , Azerbaijan.
authors.forename: Afsun
authors.initials: A
authors.lastname: Sujayev
authors.affiliation: b Department of Chemistry , Faculty of Sciences, Ataturk University , Erzurum , Turkey.
authors.forename: Zeynebe
authors.initials: Z
authors.lastname: Bingol
authors.affiliation: b Department of Chemistry , Faculty of Sciences, Ataturk University , Erzurum , Turkey.
authors.forename: Songul
authors.initials: S
authors.lastname: Çetinkaya
authors.affiliation: b Department of Chemistry , Faculty of Sciences, Ataturk University , Erzurum , Turkey.|c Department of Zoology , College of Science, King Saud University , Riyadh-Saudi , Arabia.
authors.forename: İlhami
authors.initials: İ
authors.lastname: Gulçin
authors.affiliation: b Department of Chemistry , Faculty of Sciences, Ataturk University , Erzurum , Turkey.
authors.forename: Sukru
authors.initials: S
authors.lastname: Beydemir
authors.affiliation: a Laboratory of Theoretical Bases of Synthesis and Action Mechanism of Additives , Institute of Chemistry of Additives, Azerbaijan National Academy of Sciences , Baku , Azerbaijan.
authors.forename: Vagif
authors.initials: V
authors.lastname: Farzaliyev
authors.affiliation: b Department of Chemistry , Faculty of Sciences, Ataturk University , Erzurum , Turkey.
authors.forename: Saleh H
authors.initials: SH
authors.lastname: Alwasel
authors.affiliation: d Dipartimento Di Chimica Ugo Schiff , Università Degli Studi Di Firenze , Firenze , Sesto Fiorentino , Italy , and.|e Neurofarba Department , Section of Pharmaceutical and Nutriceutical Sciences, Università Degli Studi Di Firenze , Florence , Sesto Fiorentino , Italy.
authors.forename: Claudiu T
authors.initials: CT
authors.lastname: Supuran
mesh_terms: D000110:Acetylcholinesterase / Q000378:metabolism*; D000975:Antioxidants / 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; D011743:Pyrimidines / Q000138:chemical synthesis / Q000737:chemistry / Q000494:pharmacology*; D013329:Structure-Activity Relationship
chemical_list: C000614226:2-thioxo-1,2,3,4-tetrahydropyrimidine; D000975:Antioxidants; D002257:Carbonic Anhydrase Inhibitors; D002800:Cholinesterase Inhibitors; D011743:Pyrimidines; D000110:Acetylcholinesterase; D002091:Butyrylcholinesterase; D024401:Carbonic Anhydrase I; D024402:Carbonic Anhydrase II
keywords: Acetylcholinesterase; antioxidant activity; butyrylcholinesterase; carbonic anhydrase; enzyme inhibition