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).

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

Piemontese L.
;
Brunetti L.;Perna F. M.;Capriati V.
2020

Abstract

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).
File in questo prodotto:
File Dimensione Formato  
Molecules 2020-1.pdf

accesso aperto

Tipologia: Documento in Versione Editoriale
Licenza: NON PUBBLICO - Accesso privato/ristretto
Dimensione 5.92 MB
Formato Adobe PDF
5.92 MB Adobe PDF Visualizza/Apri

I documenti in IRIS sono protetti da copyright e tutti i diritti sono riservati, salvo diversa indicazione.

Utilizza questo identificativo per citare o creare un link a questo documento: http://hdl.handle.net/11586/256450
Citazioni
  • ???jsp.display-item.citation.pmc??? 7
  • Scopus 15
  • ???jsp.display-item.citation.isi??? 14
social impact