Abstract

The enantiomer separation of a number of racemic 7-[(1-alkylpiperidin-3-yl)methoxy]coumarin derivatives, some of which show outstanding in vitro multitarget neuroprotective activities, was successfully achieved on a polysaccharide-based chiral stationary phase, bearing amylose tris(3,5-dimethylphenylcarbamate) as chiral selector, in normal polar mode (methanol and acetonitrile as the mobile phases). The majority of the screened selectands, especially those bearing 1-(3-X-benzyl)piperidin-3-yl moieties, showed baseline enantiomer separations, and compound 8 (X = NO2) was the best resolved (α = 2.01; RS = 4.27). Linear free-energy relationships, usefully complemented by molecular docking calculations, proved the key role in enantioselective retention of aromatic interactions between π-donor moieties in the chiral selector and π-acceptor moieties in selectand, strengthened by hydrogen bond interaction between a hydrogen bond donor in the chiral selector and the hydrogen bond acceptor group(s) in the selectand. Statistically reliable equations highlighted the importance of the substituent's size and substitution pattern (meta better than para) to affect the enantiorecognition of the title compounds. The chromatographic data support the scalability of the optimized experimental conditions for preparative purposes. This article is protected by copyright. All rights reserved.

Autore Pugliese

• Carrieri Antonio , Altomare Cosimo Damiano , Pisani Leonardo , Catto Marco , De Candia Modesto , Cellamare Saverio

Tutti gli autori

• CARRIERI A.;ALTOMARE C.D.;PISANI L.;CATTO M.;RULLO M.;DE CANDIA M.;CELLAMARE S.

Titolo volume/Rivista

Non Disponibile

Anno di pubblicazione

2018

ISSN

1615-9306

ISBN

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Numero di citazioni Wos

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Settori ERC

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Codici ASJC

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