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Open AccessFeature PaperArticle

Deep Eutectic Solvents as Effective Reaction Media for the Synthesis of 2-Hydroxyphenylbenzimidazole-Based Scaffolds en Route to Donepezil-Like Compounds

1
Dipartimento di Farmacia–Scienze del Farmaco, Università degli Studi di Bari «Aldo Moro», Via E. Orabona 4, I-70125 Bari, Italy
2
Consorzio C.I.N.M.P.I.S., Via E. Orabona 4, I-70125 Bari, Italy
3
Centro de Química Estrutural, Instituto Superior Técnico, Universidade de Lisboa, Av. Rovisco Pais 1, 1049-001 Lisboa, Portugal
*
Authors to whom correspondence should be addressed.
Academic Editor: Paula Sério Branco
Molecules 2020, 25(3), 574; https://doi.org/10.3390/molecules25030574
Received: 19 December 2019 / Revised: 18 January 2020 / Accepted: 27 January 2020 / Published: 28 January 2020
(This article belongs to the Special Issue Development of New Methods of Synthesis of Heterocycles)
An unsubstituted 2-hydroxyphenylbenzimidazole has recently been included as a scaffold in a series of hybrids (including the hit compound PZ1) based on the framework of the acetylcholinesterase (AChE) inhibitor Donepezil, which is a new promising multi-target ligand in Alzheimer’s disease (AD) treatment. Building upon these findings, we have now designed and completed the whole synthesis of PZ1 in the so-called deep eutectic solvents (DESs), which have emerged as an unconventional class of bio-renewable reaction media in green synthesis. Under optimized reaction conditions, the preparation of a series of 2-hydroxyphenylbenzimidazole-based nuclei has also been perfected in DESs, and comparison with other routes which employ toxic and volatile organic solvents (VOCs) provided. The functionalization of the aromatic ring can have implications on some important biological properties of the described derivatives and will be the subject of future studies of structure-activity relationships (SARs). View Full-Text
Keywords: deep eutectic solvents; 2-hydroxyphenylbenzimidazole; Alzheimer’s disease deep eutectic solvents; 2-hydroxyphenylbenzimidazole; Alzheimer’s disease
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MDPI and ACS Style

Piemontese, L.; Sergio, R.; Rinaldo, F.; Brunetti, L.; Perna, F.M.; Santos, M.A.; Capriati, V. Deep Eutectic Solvents as Effective Reaction Media for the Synthesis of 2-Hydroxyphenylbenzimidazole-Based Scaffolds en Route to Donepezil-Like Compounds. Molecules 2020, 25, 574. https://doi.org/10.3390/molecules25030574

AMA Style

Piemontese L, Sergio R, Rinaldo F, Brunetti L, Perna FM, Santos MA, Capriati V. Deep Eutectic Solvents as Effective Reaction Media for the Synthesis of 2-Hydroxyphenylbenzimidazole-Based Scaffolds en Route to Donepezil-Like Compounds. Molecules. 2020; 25(3):574. https://doi.org/10.3390/molecules25030574

Chicago/Turabian Style

Piemontese, Luca; Sergio, Roberta; Rinaldo, Federica; Brunetti, Leonardo; Perna, Filippo M.; Santos, M. A.; Capriati, Vito. 2020. "Deep Eutectic Solvents as Effective Reaction Media for the Synthesis of 2-Hydroxyphenylbenzimidazole-Based Scaffolds en Route to Donepezil-Like Compounds" Molecules 25, no. 3: 574. https://doi.org/10.3390/molecules25030574

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