期刊
BIOORGANIC & MEDICINAL CHEMISTRY
卷 21, 期 7, 页码 1735-1748出版社
PERGAMON-ELSEVIER SCIENCE LTD
DOI: 10.1016/j.bmc.2013.01.052
关键词
6-Fluorobenzo[d]thiazole; Lipophilicity; Acetylcholinesterase; Butyrylcholinesterase; Cholinesterase inhibition; In vitro cytotoxicity; Molecular docking; Structure-activity relationships
资金
- Faculty of Chemistry and Chemical Technology, University of Pardubice
- Charles University in Prague [SW 267 003]
- [SGFChT07/2013]
A series of novel cholinesterase inhibitors based on 2-substituted 6-fluorobenzo[d]thiazole were synthesised and characterised by IR, H-1, C-13 and F-19 NMR spectroscopy and HRMS. Purity was checked by elemental analyses. The novel carbamates were tested for their ability to inhibit acetylcholinesterase (AChE) and butyrylcholinesterase (BChE). The toxicity of the most active compounds was investigated using a standard in vitro test with HepG2 cells, and the ratio between biological activity and toxicity was determined. In addition, the toxicity of the most active compounds was evaluated against MCF7 cells using the xCELLigence system. Structure-activity relationships reflecting the dependence of cholinesterase inhibitors on the lipophilicity of the compounds as well as on the Taft polar and steric substituent constants are discussed. The specific orientation of the inhibitors in the binding site of acetylcholinesterase was determined using molecular docking of the most active compound. (C) 2013 Elsevier Ltd. All rights reserved.
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