Synthesis, Characterization, Acetylcholinesterase Inhibition, Molecular Modeling and Antioxidant Activities of Some Novel Schiff Bases Derived from 1-(2-Ketoiminoethyl)piperazines

Molecules

Saleh M. Salga¹  Hapipah M. Ali¹  Mahmood A. Abdullah¹  Siddig I. Abdelwahab¹  Lam Kok Wai¹  Michael J. C. Buckle¹  Sri Devi Sukumaran¹ 

[1] ¹Department of Chemistry, University of Malaya, Kuala Lumpur, 50603, Malaysia

关键词: 1-(2-ketoiminoethyl)piperazines;    AChE inhibition;    molecular docking;    antioxidant study;    acute toxicity;   

DOI  :  10.3390/molecules16119316

来源: mdpi

【 摘 要 】

Some novel Schiff bases derived from 1-(2-ketoiminoethyl)piperazines were synthesized and characterized by mass spectroscopy, FTIR, UV-Visible, ¹H and ¹³C-NMR. The compounds were tested for inhibitory activities on human acetylcholinesterase (hAChE), antioxidant activities, acute oral toxicity and further studied by molecular modeling techniques. The study identified the compound (DHP) to have the highest activity among the series in hAChE inhibition and DPPH assay while the compound LP revealed the highest activity in the FRAP assay. The hAChE inhibitory activity of DHP is comparable with that of propidium, a known AChE inhibitor. This high activity of DHP was checked by molecular modeling which showed that DHP could not be considered as a bivalent ligand due to its incapability to occupy the esteratic site (ES) region of the 3D crystal structure of hAChE. The antioxidant study unveiled varying results in 1,1-diphenyl-1-picrylhydrazyl (DPPH) and ferric reducing antioxidant power (FRAP) assays. This indicates mechanistic variations of the compounds in the two assays. The potential therapeutic applications and safety of these compounds were suggested for use as human acetylcholinesterase inhibitors and antioxidants.

【 授权许可】

CC BY   
This is an open access article distributed under the Creative Commons Attribution License (CC BY) which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited.