Synthesis, characterization, acetylcholinesterase inhibition, molecular modeling and antioxidant activities of some novel schiff bases derived from 1-(2-ketoiminoethyl)piperazines

Saleh M. Salga, Hapipah M. Ali, Mahmood A. Abdullah, Siddig I. Abdelwahab, Kok Wai Lam, Michael J C Buckle, Sri Devi Sukumaran, A. Hamid A Hadi

Research output: Contribution to journalArticle

14 Citations (Scopus)

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.

Original languageEnglish
Pages (from-to)9316-9330
Number of pages15
JournalMolecules
Volume16
Issue number11
DOIs
Publication statusPublished - Nov 2011

Fingerprint

Piperazines
Molecular modeling
Schiff Bases
antioxidants
Acetylcholinesterase
imines
Antioxidants
Assays
synthesis
inhibitors
Propidium
Cholinesterase Inhibitors
Fourier Transform Infrared Spectroscopy
Ultraviolet spectroscopy
Human Activities
Toxicity
Mass Spectrometry
toxicity
Crystal structure
Nuclear magnetic resonance

Keywords

  • 1-(2-ketoiminoethyl)piperazines
  • AChE inhibition
  • Acute toxicity
  • Antioxidant study
  • Molecular docking

ASJC Scopus subject areas

  • Organic Chemistry

Cite this

Synthesis, characterization, acetylcholinesterase inhibition, molecular modeling and antioxidant activities of some novel schiff bases derived from 1-(2-ketoiminoethyl)piperazines. / Salga, Saleh M.; Ali, Hapipah M.; Abdullah, Mahmood A.; Abdelwahab, Siddig I.; Lam, Kok Wai; Buckle, Michael J C; Sukumaran, Sri Devi; Hadi, A. Hamid A.

In: Molecules, Vol. 16, No. 11, 11.2011, p. 9316-9330.

Research output: Contribution to journalArticle

Salga, Saleh M. ; Ali, Hapipah M. ; Abdullah, Mahmood A. ; Abdelwahab, Siddig I. ; Lam, Kok Wai ; Buckle, Michael J C ; Sukumaran, Sri Devi ; Hadi, A. Hamid A. / Synthesis, characterization, acetylcholinesterase inhibition, molecular modeling and antioxidant activities of some novel schiff bases derived from 1-(2-ketoiminoethyl)piperazines. In: Molecules. 2011 ; Vol. 16, No. 11. pp. 9316-9330.
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