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Molecules 2011, 16(11), 9316-9330; doi:10.3390/molecules16119316

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

1
Department of Chemistry, University of Malaya, Kuala Lumpur, 50603, Malaysia
2
Department of Molecular Medicine, University of Malaya, Kuala Lumpur, 50603, Malaysia
3
Department of Pharmacy, University of Malaya, Kuala Lumpur, 50603, Malaysia
4
Faculty of Pharmacy, Universiti Kebangsaan Malaysia, Jalan Raja Muda Abdul Aziz, Kuala Lumpur, 50300, Malaysia
*
Authors to whom correspondence should be addressed.
Received: 2 August 2011 / Revised: 22 October 2011 / Accepted: 24 October 2011 / Published: 7 November 2011
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Abstract

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.
Keywords: 1-(2-ketoiminoethyl)piperazines; AChE inhibition; molecular docking; antioxidant study; acute toxicity 1-(2-ketoiminoethyl)piperazines; AChE inhibition; molecular docking; antioxidant study; acute toxicity
This is an open access article distributed under the Creative Commons Attribution License (CC BY 3.0).

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MDPI and ACS Style

Salga, S.M.; Ali, H.M.; Abdullah, M.A.; Abdelwahab, S.I.; Wai, L.K.; Buckle, M.J.C.; Sukumaran, S.D.; Hadi, A.H.A. Synthesis, Characterization, Acetylcholinesterase Inhibition, Molecular Modeling and Antioxidant Activities of Some Novel Schiff Bases Derived from 1-(2-Ketoiminoethyl)piperazines. Molecules 2011, 16, 9316-9330.

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