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Molecules 2012, 17(3), 2408-2427; doi:10.3390/molecules17032408

Synthesis, Characterization, X-ray Crystallography, Acetyl Cholinesterase Inhibition and Antioxidant Activities of Some Novel Ketone Derivatives of Gallic Hydrazide-Derived Schiff Bases

1
Department of Chemistry, Faculty of Science, University of Malaya, Kuala Lumpur 50603, Malaysia
2
Department of Molecular Medicine, Faculty of Medicine, University of Malaya, Kuala Lumpur 50603, Malaysia
3
Departments of Pharmacy, Faculty of Medicine, University of Malaya, Kuala Lumpur 50603, Malaysia
*
Authors to whom correspondence should be addressed.
Received: 28 January 2012 / Revised: 21 February 2012 / Accepted: 23 February 2012 / Published: 28 February 2012
(This article belongs to the Section Medicinal Chemistry)
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Abstract

Alzheimer’s disease (AD) is the most common form of dementia among older people and the pathogenesis of this disease is associated with oxidative stress. Acetylcholinesterase inhibitors with antioxidant activities are considered potential treatments for AD. Some novel ketone derivatives of gallic hydrazide-derived Schiff bases were synthesized and examined for their antioxidant activities and in vitro and in silico acetyl cholinesterase inhibition. The compounds were characterized using spectroscopy and X-ray crystallography. The ferric reducing antioxidant power (FRAP) and 2,2-diphenyl-1-picrylhydrazyl (DPPH) assays revealed that all the compounds have strong antioxidant activities. N-(1-(5-bromo-2-hydroxyphenyl)-ethylidene)-3,4,5-trihydroxybenzohydrazide (2) was the most potent inhibitor of human acetyl cholinesterase, giving an inhibition rate of 77% at 100 μM. Molecular docking simulation of the ligand-enzyme complex suggested that the ligand may be positioned in the enzyme’s active-site gorge, interacting with residues in the peripheral anionic subsite (PAS) and acyl binding pocket (ABP). The current work warrants further preclinical studies to assess the potential for these novel compounds for the treatment of AD.
Keywords: gallic hydrazide Schiff bases; AChE inhibition; antioxidant study; molecular docking gallic hydrazide Schiff bases; AChE inhibition; antioxidant study; molecular docking
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MDPI and ACS Style

Gwaram, N.S.; Ali, H.M.; Abdulla, M.A.; Buckle, M.J.C.; Sukumaran, S.D.; Chung, L.Y.; Othman, R.; Alhadi, A.A.; Yehye, W.A.; Hadi, A.H.A.; Hassandarvish, P.; Khaledi, H.; Abdelwahab, S.I. Synthesis, Characterization, X-ray Crystallography, Acetyl Cholinesterase Inhibition and Antioxidant Activities of Some Novel Ketone Derivatives of Gallic Hydrazide-Derived Schiff Bases. Molecules 2012, 17, 2408-2427.

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