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Synthesis and investigation of the conversion reactions of pyrimidine-thiones with nucleophilic reagent and evaluation of their acetylcholinesterase, carbonic anhydrase inhibition, and antioxidant activities.
J Biochem Mol Toxicol. 2018 Feb; 32(2)JB

Abstract

The conversion reactions of pyrimidine-thiones with nucleophilic reagent were studied during this scientific research. For this purpose, new compounds were synthesized by the interaction between 1,2-epoxy propane, 1,2-epoxy butane, and 4-chlor-1-butanol and pyrimidine-thiones. These pyrimidine-thiones derivatives (A-K) showed good inhibitory action against acetylcholinesterase (AChE), and human carbonic anhydrase (hCA) isoforms I and II. AChE inhibition was in the range of 93.1 ± 33.7-467.5 ± 126.9 nM. The hCA I and II were effectively inhibited by these compounds, with Ki values in the range of 4.3 ± 1.1-9.1 ± 2.7 nM for hCA I and 4.2 ± 1.1-14.1 ± 4.4 nM for hCA II. On the other hand, acetazolamide clinically used as CA inhibitor showed Ki value of 13.9 ± 5.1 nM against hCA I and 18.1 ± 8.5 nM against hCA II. The antioxidant activity of the pyrimidine-thiones derivatives (A-K) was investigated by using different in vitro antioxidant assays, including Cu2+ and Fe3+ reducing, 1,1-diphenyl-2-picrylhydrazyl (DPPH•) radical scavenging, and Fe2+ chelating activities.

Authors+Show Affiliations

Department of Chemistry, Faculty of Sciences, Ataturk University, Erzurum 25240, Turkey.Laboratory of Theoretical Bases of Synthesis and Action Mechanism of Additives, Institute of Chemistry of Additives, Azerbaijan National Academy of Sciences, Baku 1029, Azerbaijan.Health Services Vocational School, Igdır University, Igdır 76000, Turkey.Laboratory of Theoretical Bases of Synthesis and Action Mechanism of Additives, Institute of Chemistry of Additives, Azerbaijan National Academy of Sciences, Baku 1029, Azerbaijan.Department of Biochemistry, Faculty of Medical, Van Yuzuncu Yil University, Van 65090, Turkey.Laboratory of Theoretical Bases of Synthesis and Action Mechanism of Additives, Institute of Chemistry of Additives, Azerbaijan National Academy of Sciences, Baku 1029, Azerbaijan.Laboratory of Theoretical Bases of Synthesis and Action Mechanism of Additives, Institute of Chemistry of Additives, Azerbaijan National Academy of Sciences, Baku 1029, Azerbaijan.Department of Chemistry, Faculty of Sciences, Ataturk University, Erzurum 25240, Turkey.

Pub Type(s)

Comparative Study
Journal Article

Language

eng

PubMed ID

29283199

Citation

Taslimi, Parham, et al. "Synthesis and Investigation of the Conversion Reactions of Pyrimidine-thiones With Nucleophilic Reagent and Evaluation of Their Acetylcholinesterase, Carbonic Anhydrase Inhibition, and Antioxidant Activities." Journal of Biochemical and Molecular Toxicology, vol. 32, no. 2, 2018.
Taslimi P, Sujayev A, Turkan F, et al. Synthesis and investigation of the conversion reactions of pyrimidine-thiones with nucleophilic reagent and evaluation of their acetylcholinesterase, carbonic anhydrase inhibition, and antioxidant activities. J Biochem Mol Toxicol. 2018;32(2).
Taslimi, P., Sujayev, A., Turkan, F., Garibov, E., Huyut, Z., Farzaliyev, V., Mamedova, S., & Gulçin, İ. (2018). Synthesis and investigation of the conversion reactions of pyrimidine-thiones with nucleophilic reagent and evaluation of their acetylcholinesterase, carbonic anhydrase inhibition, and antioxidant activities. Journal of Biochemical and Molecular Toxicology, 32(2). https://doi.org/10.1002/jbt.22019
Taslimi P, et al. Synthesis and Investigation of the Conversion Reactions of Pyrimidine-thiones With Nucleophilic Reagent and Evaluation of Their Acetylcholinesterase, Carbonic Anhydrase Inhibition, and Antioxidant Activities. J Biochem Mol Toxicol. 2018;32(2) PubMed PMID: 29283199.
* Article titles in AMA citation format should be in sentence-case
TY - JOUR T1 - Synthesis and investigation of the conversion reactions of pyrimidine-thiones with nucleophilic reagent and evaluation of their acetylcholinesterase, carbonic anhydrase inhibition, and antioxidant activities. AU - Taslimi,Parham, AU - Sujayev,Afsun, AU - Turkan,Fikret, AU - Garibov,Emin, AU - Huyut,Zübeyir, AU - Farzaliyev,Vagif, AU - Mamedova,Sevgi, AU - Gulçin,İlhami, Y1 - 2017/12/28/ PY - 2017/10/30/received PY - 2017/11/21/revised PY - 2017/11/28/accepted PY - 2017/12/29/pubmed PY - 2018/6/19/medline PY - 2017/12/29/entrez KW - acetylcholinesterase KW - antioxidant activity KW - carbonic anhydrase KW - enzyme inhibition KW - pyrimidine-thiones JF - Journal of biochemical and molecular toxicology JO - J. Biochem. Mol. Toxicol. VL - 32 IS - 2 N2 - The conversion reactions of pyrimidine-thiones with nucleophilic reagent were studied during this scientific research. For this purpose, new compounds were synthesized by the interaction between 1,2-epoxy propane, 1,2-epoxy butane, and 4-chlor-1-butanol and pyrimidine-thiones. These pyrimidine-thiones derivatives (A-K) showed good inhibitory action against acetylcholinesterase (AChE), and human carbonic anhydrase (hCA) isoforms I and II. AChE inhibition was in the range of 93.1 ± 33.7-467.5 ± 126.9 nM. The hCA I and II were effectively inhibited by these compounds, with Ki values in the range of 4.3 ± 1.1-9.1 ± 2.7 nM for hCA I and 4.2 ± 1.1-14.1 ± 4.4 nM for hCA II. On the other hand, acetazolamide clinically used as CA inhibitor showed Ki value of 13.9 ± 5.1 nM against hCA I and 18.1 ± 8.5 nM against hCA II. The antioxidant activity of the pyrimidine-thiones derivatives (A-K) was investigated by using different in vitro antioxidant assays, including Cu2+ and Fe3+ reducing, 1,1-diphenyl-2-picrylhydrazyl (DPPH•) radical scavenging, and Fe2+ chelating activities. SN - 1099-0461 UR - https://www.unboundmedicine.com/medline/citation/29283199/Synthesis_and_investigation_of_the_conversion_reactions_of_pyrimidine_thiones_with_nucleophilic_reagent_and_evaluation_of_their_acetylcholinesterase_carbonic_anhydrase_inhibition_and_antioxidant_activities_ L2 - https://doi.org/10.1002/jbt.22019 DB - PRIME DP - Unbound Medicine ER -