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Synthesis and biological evaluation of aminomethyl and alkoxymethyl derivatives as carbonic anhydrase, acetylcholinesterase and butyrylcholinesterase inhibitors.
J Enzyme Inhib Med Chem. 2017 Dec; 32(1):1174-1182.JE

Abstract

Compounds containing nitrogen and sulfur atoms can be widely used in various fields such as industry, medicine, biotechnology and chemical technology. Therefore, the reactions of aminomethylation and alkoxymethylation of mercaptobenzothiazole, mercaptobenzoxazole and 2-aminothiazole were developed. Additionally, the alkoxymethyl derivatives of mercaptobenzoxazole and 2-aminothiazole were synthesized by a reaction with hemiformals, which are prepared by the reaction of alcohols and formaldehyde. In this study, the inhibitory effects of these molecules were investigated against acetylcholinesterase (AChE), butyrylcholinesterase (BChE) enzymes and carbonic anhydrase I, and II isoenzymes (hCA I and II). Both hCA isoenzymes were significantly inhibited by the recently synthesized molecules, with Ki values in the range of 58-157 nM for hCA I, and 81-215 nM for hCA II. Additionally, the Ki parameters of these molecules for BChE and AChE were calculated in the ranges 23-88 and 18-78 nM, respectively.

Authors+Show Affiliations

a Department of Chemistry, Faculty of Sciences , Ataturk University , Erzurum , Turkey. b Department of Zoology, College of Science , King Saud University , Riyadh , Saudi Arabia.c Laboratory of Theoretical Bases of Synthesis and Action Mechanism of Additives , Institute of Chemistry of Additives, Azerbaijan National Academy of Sciences , Baku , Azerbaijan.a Department of Chemistry, Faculty of Sciences , Ataturk University , Erzurum , Turkey.d Department of Biochemistry, Faculty of Medical , Yüzüncü Yıl University , Van , Turkey.c Laboratory of Theoretical Bases of Synthesis and Action Mechanism of Additives , Institute of Chemistry of Additives, Azerbaijan National Academy of Sciences , Baku , Azerbaijan.c Laboratory of Theoretical Bases of Synthesis and Action Mechanism of Additives , Institute of Chemistry of Additives, Azerbaijan National Academy of Sciences , Baku , Azerbaijan.c Laboratory of Theoretical Bases of Synthesis and Action Mechanism of Additives , Institute of Chemistry of Additives, Azerbaijan National Academy of Sciences , Baku , Azerbaijan.e Department of Biochemistry, Faculty of Pharmacy , Anadolu University , Eskişehir , Turkey.b Department of Zoology, College of Science , King Saud University , Riyadh , Saudi Arabia.f Dipartimento di Chimica Ugo Schiff , Universita degli Studi di Firenze , Florence , Italy. g Neurofarba Department, Section of Pharmaceutical and Nutriceutical Sciences , Universita degli Studi di Firenze , Florence , Italy.

Pub Type(s)

Journal Article

Language

eng

PubMed ID

28891347

Citation

Gulçin, İlhami, et al. "Synthesis and Biological Evaluation of Aminomethyl and Alkoxymethyl Derivatives as Carbonic Anhydrase, Acetylcholinesterase and Butyrylcholinesterase Inhibitors." Journal of Enzyme Inhibition and Medicinal Chemistry, vol. 32, no. 1, 2017, pp. 1174-1182.
Gulçin İ, Abbasova M, Taslimi P, et al. Synthesis and biological evaluation of aminomethyl and alkoxymethyl derivatives as carbonic anhydrase, acetylcholinesterase and butyrylcholinesterase inhibitors. J Enzyme Inhib Med Chem. 2017;32(1):1174-1182.
Gulçin, İ., Abbasova, M., Taslimi, P., Huyut, Z., Safarova, L., Sujayev, A., Farzaliyev, V., Beydemir, Ş., Alwasel, S. H., & Supuran, C. T. (2017). Synthesis and biological evaluation of aminomethyl and alkoxymethyl derivatives as carbonic anhydrase, acetylcholinesterase and butyrylcholinesterase inhibitors. Journal of Enzyme Inhibition and Medicinal Chemistry, 32(1), 1174-1182. https://doi.org/10.1080/14756366.2017.1368019
Gulçin İ, et al. Synthesis and Biological Evaluation of Aminomethyl and Alkoxymethyl Derivatives as Carbonic Anhydrase, Acetylcholinesterase and Butyrylcholinesterase Inhibitors. J Enzyme Inhib Med Chem. 2017;32(1):1174-1182. PubMed PMID: 28891347.
* Article titles in AMA citation format should be in sentence-case
TY - JOUR T1 - Synthesis and biological evaluation of aminomethyl and alkoxymethyl derivatives as carbonic anhydrase, acetylcholinesterase and butyrylcholinesterase inhibitors. AU - Gulçin,İlhami, AU - Abbasova,Malahat, AU - Taslimi,Parham, AU - Huyut,Zübeyir, AU - Safarova,Leyla, AU - Sujayev,Afsun, AU - Farzaliyev,Vagif, AU - Beydemir,Şükrü, AU - Alwasel,Saleh H, AU - Supuran,Claudiu T, PY - 2017/9/12/entrez PY - 2017/9/12/pubmed PY - 2017/10/11/medline KW - Acetylcholinesterase KW - butyrylcholinesterase KW - carbonic anhydrase KW - mercaptobenzothiazole KW - mercaptobenzoxazole SP - 1174 EP - 1182 JF - Journal of enzyme inhibition and medicinal chemistry JO - J Enzyme Inhib Med Chem VL - 32 IS - 1 N2 - Compounds containing nitrogen and sulfur atoms can be widely used in various fields such as industry, medicine, biotechnology and chemical technology. Therefore, the reactions of aminomethylation and alkoxymethylation of mercaptobenzothiazole, mercaptobenzoxazole and 2-aminothiazole were developed. Additionally, the alkoxymethyl derivatives of mercaptobenzoxazole and 2-aminothiazole were synthesized by a reaction with hemiformals, which are prepared by the reaction of alcohols and formaldehyde. In this study, the inhibitory effects of these molecules were investigated against acetylcholinesterase (AChE), butyrylcholinesterase (BChE) enzymes and carbonic anhydrase I, and II isoenzymes (hCA I and II). Both hCA isoenzymes were significantly inhibited by the recently synthesized molecules, with Ki values in the range of 58-157 nM for hCA I, and 81-215 nM for hCA II. Additionally, the Ki parameters of these molecules for BChE and AChE were calculated in the ranges 23-88 and 18-78 nM, respectively. SN - 1475-6374 UR - https://www.unboundmedicine.com/medline/citation/28891347/Synthesis_and_biological_evaluation_of_aminomethyl_and_alkoxymethyl_derivatives_as_carbonic_anhydrase_acetylcholinesterase_and_butyrylcholinesterase_inhibitors_ L2 - http://www.tandfonline.com/doi/full/10.1080/14756366.2017.1368019 DB - PRIME DP - Unbound Medicine ER -