Tags

Type your tag names separated by a space and hit enter

Synthesis, Biological Evaluation and Molecular Docking Study of Hydrazone-Containing Pyridinium Salts as Cholinesterase Inhibitors.
Chem Pharm Bull (Tokyo). 2016; 64(9):1281-7.CP

Abstract

A series of pyridinium salts bearing alkylphenyl groups at 1 position and hydrazone structure at 4 position of the pyridinium ring were synthesized and evaluated for the inhibition of both acetylcholinesterase (AChE) and butyrylcholinesterase (BuChE) enzymes. The cholinesterase (ChE) inhibitory activity studies were carried out by using the Ellman's colorimetric method. All compounds displayed considerable AChE and BuChE inhibitory activity and some of the compounds manifested remarkable anti-AChE activity compared to the reference compound, galantamine. Among the title compounds, the series including benzofuran aromatic ring exhibited the best inhibitory activity both on AChE and BuChE enzymes. Compound 3b, 4-[2-(1-(benzofuran-2-yl)ethylidene)hydrazinyl]-1-(3-phenylpropyl)pyridinium bromide, was the most active compound with IC50 value of 0.23 (0.24) µM against enantiomeric excess (ee)AChE (human (h)AChE) while compound 3a, 4-[2-(1-(benzofuran-2-yl)ethylidene)hydrazinyl]-1-phenethylpyridinium bromide, was the most active compound with IC50 value of 0.95 µM against BuChE. Moreover, 3a and b exhibited higher activity than the reference compound galantamine (eeAChE (hAChE) IC50 0.43 (0.52) µM; BuChE IC50 14.92 µM). Molecular docking studies were carried out on 3b having highest inhibitory activity against AChE.

Authors+Show Affiliations

Department of Pharmaceutical Chemistry, Faculty of Pharmacy, Ege University.No affiliation info availableNo affiliation info availableNo affiliation info availableNo affiliation info available

Pub Type(s)

Journal Article

Language

eng

PubMed ID

27581632

Citation

Parlar, Sulunay, et al. "Synthesis, Biological Evaluation and Molecular Docking Study of Hydrazone-Containing Pyridinium Salts as Cholinesterase Inhibitors." Chemical & Pharmaceutical Bulletin, vol. 64, no. 9, 2016, pp. 1281-7.
Parlar S, Bayraktar G, Tarikogullari AH, et al. Synthesis, Biological Evaluation and Molecular Docking Study of Hydrazone-Containing Pyridinium Salts as Cholinesterase Inhibitors. Chem Pharm Bull (Tokyo). 2016;64(9):1281-7.
Parlar, S., Bayraktar, G., Tarikogullari, A. H., Alptüzün, V., & Erciyas, E. (2016). Synthesis, Biological Evaluation and Molecular Docking Study of Hydrazone-Containing Pyridinium Salts as Cholinesterase Inhibitors. Chemical & Pharmaceutical Bulletin, 64(9), 1281-7. https://doi.org/10.1248/cpb.c16-00221
Parlar S, et al. Synthesis, Biological Evaluation and Molecular Docking Study of Hydrazone-Containing Pyridinium Salts as Cholinesterase Inhibitors. Chem Pharm Bull (Tokyo). 2016;64(9):1281-7. PubMed PMID: 27581632.
* Article titles in AMA citation format should be in sentence-case
TY - JOUR T1 - Synthesis, Biological Evaluation and Molecular Docking Study of Hydrazone-Containing Pyridinium Salts as Cholinesterase Inhibitors. AU - Parlar,Sulunay, AU - Bayraktar,Gulsah, AU - Tarikogullari,Ayse Hande, AU - Alptüzün,Vildan, AU - Erciyas,Ercin, PY - 2016/9/2/entrez PY - 2016/9/2/pubmed PY - 2017/2/7/medline SP - 1281 EP - 7 JF - Chemical & pharmaceutical bulletin JO - Chem Pharm Bull (Tokyo) VL - 64 IS - 9 N2 - A series of pyridinium salts bearing alkylphenyl groups at 1 position and hydrazone structure at 4 position of the pyridinium ring were synthesized and evaluated for the inhibition of both acetylcholinesterase (AChE) and butyrylcholinesterase (BuChE) enzymes. The cholinesterase (ChE) inhibitory activity studies were carried out by using the Ellman's colorimetric method. All compounds displayed considerable AChE and BuChE inhibitory activity and some of the compounds manifested remarkable anti-AChE activity compared to the reference compound, galantamine. Among the title compounds, the series including benzofuran aromatic ring exhibited the best inhibitory activity both on AChE and BuChE enzymes. Compound 3b, 4-[2-(1-(benzofuran-2-yl)ethylidene)hydrazinyl]-1-(3-phenylpropyl)pyridinium bromide, was the most active compound with IC50 value of 0.23 (0.24) µM against enantiomeric excess (ee)AChE (human (h)AChE) while compound 3a, 4-[2-(1-(benzofuran-2-yl)ethylidene)hydrazinyl]-1-phenethylpyridinium bromide, was the most active compound with IC50 value of 0.95 µM against BuChE. Moreover, 3a and b exhibited higher activity than the reference compound galantamine (eeAChE (hAChE) IC50 0.43 (0.52) µM; BuChE IC50 14.92 µM). Molecular docking studies were carried out on 3b having highest inhibitory activity against AChE. SN - 1347-5223 UR - https://www.unboundmedicine.com/medline/citation/27581632/Synthesis_Biological_Evaluation_and_Molecular_Docking_Study_of_Hydrazone_Containing_Pyridinium_Salts_as_Cholinesterase_Inhibitors_ L2 - https://doi.org/10.1248/cpb.c16-00221 DB - PRIME DP - Unbound Medicine ER -