2-Phenylbenzofuran derivatives as butyrylcholinesterase inhibitors: Synthesis, biological activity and molecular modeling

Delogu, Giovanna; Matos, María Joäo; Fanti, Maura; Era, Benedetta; Pieroni, E.; Fais, Antonella; Kumar, Amit; Pintus, Francesca

doi:10.1016/j.bmcl.2016.03.039

Cited by 47 publications

(41 citation statements)

References 40 publications

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“…Delogu et al. describe the synthesis of a library of 2‐phenylbenzofuran compounds (Figure ) and evaluate their activity against cholinesterase (CHE) . Among the compounds in the library, compound 25 a (Figure ) shows the highest BuChE inhibition with an IC 50 value of 30.3 μ m .…”

Section: Discussionmentioning

confidence: 99%

Benzofuran and Indole: Promising Scaffolds for Drug Development in Alzheimer's Disease

2018

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Alzheimer's disease (AD) is a progressive neurodegenerative disease with no clinically accepted treatment to cure or halt its progression. The Food and Drug Administration has approved drugs (e.g., rivastigmine, donepezil, galantamine, and memantine) that at best provide marginal benefits, thus emphasizing the urgent need to explore other molecular entities as future drug candidates for AD. Looking at the wide pharmaceutical applications of heterocyclic compounds and particularly those containing benzofuran and indole ring systems, these molecular frameworks have drawn special attention from medicinal chemists for further evaluation in numerous diseases. This article focuses on the history and recent advances of benzofuran- and indole-based compounds as inhibitors of butyrylcholinesterase, acetylcholinesterase, γ-secretase, β-secretase, tau misfolding, and β-amyloid aggregation.

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Section: Discussionmentioning

confidence: 99%

Benzofuran and Indole: Promising Scaffolds for Drug Development in Alzheimer's Disease

2018

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“…In each extract total free radical-scavenging molecules were determined by ABTS + (2,2′-azinobis-(3-ethylbenzothiazoline-6-sulfonic acid) and DPPH (2,2-diphenyl-1-picrylhydrazyl) methods as previously reported [19, 20]. For both free radical methods, 6-hydroxy-2,5,7,8-tetramethylchromane-2-carboxylic acid (Trolox) was used as standard reference.…”

Section: Methodsmentioning

confidence: 99%

Tyrosinase inhibition and antioxidant properties of Asphodelus microcarpus extracts

Petrillo

González-Paramás

Era

et al. 2016

BMC Complement Altern Med

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Background Asphodelus microcarpus belongs to the family Liliaceae that include several medicinal plants. In the traditional medicine plants of the genus Asphodelus are used to treat skin disorders such as ectodermal parasites, psoriasis, microbial infection and for lightening freckles. In order to find novel skin depigmenting agents, the present work was carry out to evaluate antioxidant activity and tyrosinase inhibitory potential of leaves, flowers and tubers extracts of A. microcarpus. The phytochemical composition of the active extract was also evaluated.MethodsThree different extracts (water, methanol and ethanol) from leaves, flowers and tubers of A. microcarpus were evaluated for their inhibitory effect on tyrosinase activity using l-3,4-dihydroxyphenylalanine (l-DOPA) as substrate. Inhibition of cellular tyrosinase activity and melanin production was also investigated in melanoma B16F10 cells. Antioxidant activity, total phenolic and flavonoids contents were determined using standard in vitro methods. HPLC-DAD-MS was used to identify phenolic profile of the active extract.ResultsThe results showed that all extracts have a direct inhibitory anti-tyrosinase activity, with ethanolic extract from flowers (FEE) exhibiting the stronger effect. Kinetic analysis revealed that FEE acts as an uncompetitive inhibitor with a Ki value of 0.19 mg/mL. The same effect was observed in murine melanoma B16F10 cells. Cellular tyrosinase activity as well as melanin content were reduced in FEE-treated cells. The results were comparable to that of the standard tyrosinase inhibitor (kojic acid). Furthermore, the same extract showed the highest antioxidant activity and an elevated levels of total phenolics and flavonoid content. Eleven phenolic components were identified as chlorogenic acid, luteolin derivates, naringenin and apigenin.ConclusionsOur findings showed that FEE from A. microcarpus inhibits tyrosinase and exerted antimelanogenesis effect in B16F10 cells. This extract also showed the highest scavenging activity, which could be mainly attributed to its high levels of total polyphenols and flavonoids. These results suggest that A. microcarpus has a great potential as sources of bioactive compounds which could be used as depigmenting agents in skin disorders.

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“…Based on the previous experimental results 4 and with the aim of finding novel and more selective AChE and BChE inhibitors, here we continue our studies, describing the synthesis, biological evaluation and docking studies of a new series of 2-phenylbenzofuran derivatives.…”

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confidence: 90%

“…In the search for finding new ChE inhibitors, we have recently reported 2-benzofurans derivatives and their inhibition activity towards both the enzymes were investigated. 4 Benzofuran scaffold has drawn considerable attention over the last few years due to its profound physiological and chemotherapeutic properties. 5 Our previous study has been the inspiration to design compounds with better inhibitory properties toward butyrylcholinesterase.…”

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confidence: 99%

<strong>Synthesis and biological activity of 2-phenylbenzofuran derivatives as butyrylcholinerase inhibitors</strong>

Delogu

Fais

Pintus

2016

Proceedings of the 20th International Electronic Conference on Synthetic Organic Chemistry

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Alzheimer disease (AD) is an irreversible and progressive brain disorder characterized by progressive memory loss and a wide range of cognitive impairments. An accepted strategy for its treatment is to restore the levels of acetylcholine by inhibiting cholinesterase enzymes, such as acetylcholinesterase (AChE) and butyrylcholinesterase (BChE). In the current paper we studied the interest of a series of 2-phenylbenzofuran derivatives as BChE inhibitors. The IC 50 values of all the compounds were determined and compared with the standard inhibitor. This work was based in our previous results and is a preliminary screening for further design and synthesis of new potential compounds that could inhibit the activity of this enzyme involved in neurodegenerative diseases.

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2-Phenylbenzofuran derivatives as butyrylcholinesterase inhibitors: Synthesis, biological activity and molecular modeling

Cited by 47 publications

References 40 publications

Benzofuran and Indole: Promising Scaffolds for Drug Development in Alzheimer's Disease

Benzofuran and Indole: Promising Scaffolds for Drug Development in Alzheimer's Disease

Tyrosinase inhibition and antioxidant properties of Asphodelus microcarpus extracts

<strong>Synthesis and biological activity of 2-phenylbenzofuran derivatives as butyrylcholinerase inhibitors</strong>

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