Chinese Journal of Organic Chemistry >
Synthesis and Biological Evaluation of 6-[(Alkylamino)-hydrazide-yl]-1-azabenzanthrone Derivatives
Received date: 2013-05-25
Revised date: 2013-09-13
Online published: 2013-09-25
Supported by
Project supported by the National Natural Science Foundation of China (No. 81260471), the Natural Science Foundation of Guangxi Province (No. 2013GXNSFAA019038) and the Key Laboratory for the Chemistry and Molecular Engineering of Medicinal Resources, Ministry of Education (No. CMEMR2012-A05).
A series of novel 6-substituted 1-azabenzanthrone derivatives have been designed and synthesized from 4-chlorophenethylamine and phthalic anhydride. Their abilities to inhibit acetylcholinesterase (AChE), butyrylcholinesterase (BChE) and AChE-induced β-amyloid (Aβ) aggregation were also tested. The synthetic compounds exhibited moderate cholinesterase inhibitory activity with IC50 values in the micromolar range in most cases. Non-competitive inhibition was found for these derivatives to AChE by the graphical analysis of steady-state inhibition data. Moreover, all compounds exhibited significant inhibitory activity on AChE-induced Aβ aggregation with inhibitory potency from 35.3% to 62.2%. Finally, eleven out of eighteen synthetic compounds were predicted to be able to cross the blood-brain barrier (BBB) to reach their targets in the central nervous system (CNS) according to a parallel artificial membrane permeation assay.
Zhong Shuming , Wei Shenqi , Liu Yun , Tang Huang . Synthesis and Biological Evaluation of 6-[(Alkylamino)-hydrazide-yl]-1-azabenzanthrone Derivatives[J]. Chinese Journal of Organic Chemistry, 2014 , 34(1) : 137 -146 . DOI: 10.6023/cjoc201305040
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