Design, synthesis and anticholinesterase activity of a novel series of 1-benzyl-4-((6-alkoxy-3-oxobenzofuran-2(3H)-ylidene) methyl) pyridinium derivatives

Nadri, Hamid; Pirali-Hamedani, Morteza; Shekarchi, Mohammad; Abdollahi, Mohammad; Sheibani, Vahid; Amanlou, Massoud; Shafiee, Abbas; Foroumadi, Alireza

doi:10.1016/j.bmc.2010.07.012

Cited by 57 publications

(30 citation statements)

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“…1), which have been confirmed in a comparison of aromatics with differing electron density. [25][26][27] Therefore, in the present study, in order to further explore the anti-Alzheimer potential of the electron-rich aromatics, a series of new inhibitors aimed at both ChEs and Ab self-induced aggregation were designed by conjugating the methylenedioxybenzene or di-(or tri-) methoxybenzene moiety with tacrine using a long chain linker. It is possible that the multialkoxybenzene inhibit AChE activity through binding with PAS of AChE and block Ab self-aggregation.…”

Section: Introductionmentioning

confidence: 99%

Design, synthesis and evaluation of novel tacrine-multialkoxybenzene hybrids as dual inhibitors for cholinesterases and amyloid beta aggregation

Luo

et al. 2011

Bioorganic & Medicinal Chemistry

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Section: Introductionmentioning

confidence: 99%

Design, synthesis and evaluation of novel tacrine-multialkoxybenzene hybrids as dual inhibitors for cholinesterases and amyloid beta aggregation

Luo

et al. 2011

Bioorganic & Medicinal Chemistry

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“…Ellman’s method was employed for determination of AChE inhibitory activity [26-28]. Acetylthiocholine was used as a substrate and hydrolysis of acetylthiocholine was determined by monitoring the formation of the yellow 5-thio-2-nitrobenzoate anion as a result of the reaction with 5,5’–dithio-bis-2-nitrobenzoic acid with thiocholine, catalyzed by enzymes at a wavelength of 412 nm.…”

Section: Methodsmentioning

confidence: 99%

A preliminary investigation of anticholinesterase activity of some Iranian medicinal plants commonly used in traditional medicine

et al. 2014

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BackgroundThe aim of this study was to evaluate acetylcholinesterase inhibitory activity of some commonly used herbal medicine in Iran to introduce a new source for management of Alzheimer’s disease. A total of 18 aqueous-methanolic extract (1:1; v/v) from the following plants: Brassica alba, Brassica nigra, Camellia sinensis, Cinchona officinalis, Citrus aurantifolia, Citrus x aurantium, Ferula assafoetida, Humulus lupulus, Juglans regia, Juniperus sabina, Myristica fragrans, Pelargonium graveolens, Pistacia vera, Punica granatum, Rheum officinale, Rosa damascena, Salix alba, and Zizyphus vulgaris were prepared and screened for their acetylcholinesterase inhibitory activity using in vitro Ellman spectrophotometric method.ResultsAccording to the obtained results, the order of inhibitory activity (IC50 values, μg /ml) of extracts from highest to the lowest was: C. sinensis (5.96), C. aurantifolia (19.57), Z. vulgaris (24.37), B. nigra (84.30) and R. damascena (93.1).ConclusionsThe results indicated and confirmed the traditional use of these herbs for management of central nervous system disorders. C. sinensis showed the highest activity in inhibition of acetylcholinesterase. However, further investigations on identification of active components in the extracts are needed.

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“…In an earlier report, we have presented the preparation and evaluation of some new ( Z )-1-benzyl-4-((6-alkoxy-3-oxobenzofuran-2(3 H )-ylidene) methyl)pyridinium (Figure 2) as AChE inhibitors [11]. Most of these compounds proved to be potent AChE inhibitors in vitro, among which compounds bearing methoxy group on position 6 of benzofuran ring showed the most activity.…”

Section: Introductionmentioning

confidence: 99%

5,6-Dimethoxybenzofuran-3-one derivatives: a novel series of dual Acetylcholinesterase/Butyrylcholinesterase inhibitors bearing benzyl pyridinium moiety

et al. 2013

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BackgroundSeveral studies have been focused on design and synthesis of multi-target anti Alzheimer compounds. Utilizing of the dual Acetylcholinesterase/Butyrylcholinesterase inhibitors has gained more interest to treat the Alzheimer’s disease. As a part of a research program to find a novel drug for treating Alzheimer disease, we have previously reported 6-alkoxybenzofuranone derivatives as potent acetylcholinesterase inhibitors. In continuation of our work, we would like to report the synthesis of 5,6-dimethoxy benzofuranone derivatives bearing a benzyl pyridinium moiety as dual Acetylcholinesterase/Butyrylcholinesterase inhibitors.MethodsThe synthesis of target compounds was carried out using a conventional method. Bayer-Villiger oxidation of 3,4-dimethoxybenzaldehyde furnished 3,4-dimethoxyphenol. The reaction of 3,4-dimethoxyphenol with chloroacetonitrile followed by treatment with HCl solution and then ring closure yielded the 5,6-dimethoxy benzofuranone. Condensation of the later compound with pyridine-4-carboxaldehyde and subsequent reaction with different benzyl halides afforded target compounds. The biological activity was measured using standard Ellman’s method. Docking studies were performed to get better insight into interaction of compounds with receptor.ResultsThe in vitro anti acetylcholinesterase/butyrylcholinesterase activity of compounds revealed that, all of the target compounds have good inhibitory activity against both Acetylcholinesterase/Butyrylcholinesterase enzymes in which compound 5b (IC50 = 52 ± 6.38nM) was the most active compound against acetylcholinesterase. The same binding mode and interactions were observed for the reference drug donepezil and compound 5b in docking study.ConclusionsIn this study, we presented a new series of benzofuranone-based derivatives having pyridinium moiety as potent dual acting Acetylcholinesterase/Butyrylcholinesterase inhibitors.

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Design, synthesis and anticholinesterase activity of a novel series of 1-benzyl-4-((6-alkoxy-3-oxobenzofuran-2(3H)-ylidene) methyl) pyridinium derivatives

Cited by 57 publications

References 21 publications

Design, synthesis and evaluation of novel tacrine-multialkoxybenzene hybrids as dual inhibitors for cholinesterases and amyloid beta aggregation

Design, synthesis and evaluation of novel tacrine-multialkoxybenzene hybrids as dual inhibitors for cholinesterases and amyloid beta aggregation

A preliminary investigation of anticholinesterase activity of some Iranian medicinal plants commonly used in traditional medicine

5,6-Dimethoxybenzofuran-3-one derivatives: a novel series of dual Acetylcholinesterase/Butyrylcholinesterase inhibitors bearing benzyl pyridinium moiety

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