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O-Hydroxyl- or o-amino benzylamine-tacrine hybrids: multifunctional biometals chelators, antioxidants, and inhibitors of cholinesterase activity and amyloid-β aggregation.

Bioorganic & medicinal chemistry (2012-09-05)
Fei Mao, Ling Huang, Zonghua Luo, Anqiu Liu, Chuanjun Lu, Zhiyong Xie, Xingshu Li
ABSTRACT

In an effort to identify novel multifunctional drug candidates for the treatment of Alzheimer's disease (AD), a series of hybrid molecules were synthesised by reacting N-(aminoalkyl)tacrine with salicylic aldehyde or derivatives of 2-aminobenzaldehyde. These compounds were then evaluated as multifunctional anti-Alzheimer's disease agents. All of the hybrids are potential biometal chelators, and in addition, most of them were better antioxidants and inhibitors of cholinesterases and amyloid-β (Aβ) aggregation than the lead compound tacrine. Compound 7c has the potential to be a candidate for AD therapy: it is a much better inhibitor of acetylcholinesterase (AChE) than tacrine (IC(50): 0.55 nM vs 109 nM), has good biometal chelation ability, is able to inhibit Aβ aggregation and has moderate antioxidant activity (1.22 Trolox equivalents).

MATERIALS
Product Number
Brand
Product Description

Sigma-Aldrich
Benzylamine, ReagentPlus®, 99%
Sigma-Aldrich
Benzylamine, purified by redistillation, ≥99.5%
Sigma-Aldrich
Benzylamine hydrochloride
Supelco
Benzylamine, for GC derivatization, LiChropur, ≥99.0%