Anthraquinone dyes. Part VI. Nuclear alkylation of 1-aminoanthraquinone leuco-derivative

Havlíčková, L.; Arient, J.

doi:10.1039/j39700000570

Cited by 2 publications

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“…The preparation of mono benzyl-(3a) and bis benzyl-(6a) 1-aminoanthraquinones has been described [8][9][10][11] but these methods are not efficient and the yields of 3a and 6a were poor. Herein, a more efficient route for the synthesis of these compounds is reported.…”

Section: Resultsmentioning

confidence: 99%

The copper(I) iodide accelerated synthesis of mono- and bisbenzyl substituted 1- and 2-aminoanthraquinones

Sui

2009

Dyes and Pigments

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Section: Resultsmentioning

confidence: 99%

The copper(I) iodide accelerated synthesis of mono- and bisbenzyl substituted 1- and 2-aminoanthraquinones

Sui

2009

Dyes and Pigments

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“…Compounds 1, 3 , 33 2 , 34 5 , 9 , 35 and 8 ( 36 ) have been achieved according to the cited references. For compound 10 ( 37 ) we applied a different synthetic route with respect to the literature; thus its experimental properties have been reported herein as follows. Naphthoquinones 4 , 6 , and 7 were obtained by reacting the 2,3-dichloro-1,4-naphthoquinone, previously suspended in ethanol or methanol, with 2 equiv of the proper amine ( Schemes 1 and 2 ).…”

Section: Resultsmentioning

confidence: 99%

Multitarget Biological Profiling of New Naphthoquinone and Anthraquinone-Based Derivatives for the Treatment of Alzheimer’s Disease

Campora

Canale

Gatta

et al. 2021

ACS Chem. Neurosci.

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Two series of naphthoquinone and anthraquinone derivatives decorated with an aromatic/heteroaromatic chain have been synthesized and evaluated as potential promiscuous agents capable of targeting different factors playing a key role in Alzheimer’s disease (AD) pathogenesis. On the basis of the in vitro biological profiling, most of them exhibited a significant ability to inhibit amyloid aggregation, PHF6 tau sequence aggregation, acetylcholinesterase (AChE), and monoamine oxidase (MAO) B. In particular, naphthoquinone 2 resulted as one of the best performing multitarget-directed ligand (MTDL) experiencing a high potency profile in inhibiting β-amyloid (Aβ 40 ) aggregation (IC 50 = 3.2 μM), PHF6 tau fragment (91% at 10 μM), AChE enzyme (IC 50 = 9.2 μM) jointly with a remarkable inhibitory activity against MAO B (IC 50 = 7.7 nM). Molecular modeling studies explained the structure–activity relationship (SAR) around the binding modes of representative compound 2 in complex with hMAO B and hAChE enzymes, revealing inhibitor/protein key contacts and the likely molecular rationale for enzyme selectivity. Compound 2 was also demonstrated to be a strong inhibitor of Aβ 42 aggregation, with potency comparable to quercetin. Accordingly, atomic force microscopy (AFM) revealed that the most promising naphthoquinones 2 and 5 and anthraquinones 11 and 12 were able to impair Aβ 42 fibrillation, deconstructing the morphologies of its fibrillar aggregates. Moreover, the same compounds exerted a moderate neuroprotective effect against Aβ 42 toxicity in primary cultures of cerebellar granule cells. Therefore, our findings demonstrate that these molecules may represent valuable chemotypes toward the development of promising candidates for AD therapy.

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Anthraquinone dyes. Part VI. Nuclear alkylation of 1-aminoanthraquinone leuco-derivative

Cited by 2 publications

References 0 publications

The copper(I) iodide accelerated synthesis of mono- and bisbenzyl substituted 1- and 2-aminoanthraquinones

The copper(I) iodide accelerated synthesis of mono- and bisbenzyl substituted 1- and 2-aminoanthraquinones

Multitarget Biological Profiling of New Naphthoquinone and Anthraquinone-Based Derivatives for the Treatment of Alzheimer’s Disease

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