Naslov
Synthesis and enantioseparation of syn- and anti- 3,5-disubstituted hydantoins by HPLC and SFC on immobilized polysaccharides-based chiral stationary phases

Autori
Jurin, Mladenka ; Kontrec, Darko ; Roje, Marin

Vrsta, podvrsta i kategorija rada
Sažeci sa skupova, sažetak, znanstveni

Izvornik
8th EuChemS Chemistry Congress : Book of Abstracts / Silva, Artur M. S. ; Galvão, Adelino M. ; Machado, Bruno F. ; Faria, Joaquim L. - Lisabon : Sociedade Portuguesa de Química, 2022, 459-459

ISBN
978-989-8124-35-7

Skup
8th EuChemS Chemistry Congress (8EuChemS)

Mjesto i datum
Lisabon, Portugal, 28.08.2022. - 01.09.2022

Vrsta sudjelovanja
Poster

Vrsta recenzije
Međunarodna recenzija

Ključne riječi
syn- and anti-3, 5-disubstituted hydantoins ; HPLC ; SFC ; enantioseparation ; immobilized polysaccharide-based chiral stationary phases

Sažetak
Imidazolidine-2, 4-diones, also well known as hydantoins, are important heterocyclic compounds in organic chemistry [1]. The hydantoin moiety is an important structural scaffold present in a number of drugs (phenytoin, ethotoine, azimilide, dantrium, nilutamide, nitrofurantoin, etc) [2, 3]. Hydantoin ring also constitute the core structure of various natural compounds from marine organisms but also from bacteria [3]. They display diverse and interesting pharmacological activities [2-5]. In conducted research the diastereomeric mixtures (syn- and anti-) of racemic 3, 5-disubstituted hydantoins 1a-i were synthesized via base-promoted intramolecular amidolysis of trans-β-lactam ureas in good yield, Scheme 1. The mixtures of diastereomeric hydantoins were then separated by preparative RP-HPLC. Each hydantoin product possesses two centers of chirality, one in the hydantoin ring and the other in the side chain. The enantioseparation of synthesized syn- and anti-3, 5-disubstituted hydantoins 1a-i was investigated on three immobilized polysaccharide- based columns (CHIRAL ART Amylose-SA, CHIRAL ART Cellulose-SB, CHIRAL ART Cellulose-SC) by HPLC using n-hexane/2-propanol (90/10, v/v) or 100% dimethyl carbonate as mobile phases, respectively, and by SFC using CO2/alcohol (methanol, ethanol, isopropanol ; 80/20, v/v) as a mobile phase. The chromatographic parameters, such as separation and resolution factors have indicated that Amylose-SA is more suitable for enantioseparation of the most analyzed syn- and anti-3, 5-disubstituted hydantoins than Celullose-SB and Cellulose-SC in both HPLC and SFC modalities. All three tested columns showed better enantiorecognition ability toward anti-hydantoins compared to syn-hydantoins, both in HPLC and SFC modes. We have demonstrated that environmentally friendly solvent dimethyl carbonate can be efficiently used as the mobile phase in HPLC mode for enantioseparation of hydantoins on the immobilized polysaccharide-based chiral stationary phases.

Izvorni jezik
Engleski

Znanstvena područja
Kemija

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