Integrated experimental and theoretical approaches to investigate the molecular mechanisms of the enantioseparation of chiral anticonvulsant and antifungal compounds
Küçük Resim Yok
Tarih
2022
Dergi Başlığı
Dergi ISSN
Cilt Başlığı
Yayıncı
Elsevier B.V.
Erişim Hakkı
info:eu-repo/semantics/closedAccess
Özet
Previously, some racemic 1-(phenyl/4-chlorophenyl)-2-(1H-triazole-1-yl)ethanol ester derivatives having a stereogenic center in their structure were synthesized and investigated for their anticonvulsant and antifungal activities. In this work, the direct enantiomeric separations of four compounds (1–4) were developed on the commercially available chiral stationary phase amylose tris(3,5-dimethyphenylcarbamate) (Chiralpak AD) in the normal phase HPLC mode. The influences of the mobile phase composition were also investigated. By mobile phase modified with n-hexane, the retention times were shorter than with methanol. The best results were obtained for all compounds (1–4) using the mobile phase of methanol/n-hexane (80:20 v/v) at a flow rate of 0.5 mL/min and the resolutions of the enantiomers were 3.38, 2.84, 1.89, and 1.53, respectively. Thus, the proposed HPLC method can facilitate further chemical and pharmacological studies on compounds 1–4 and their enantiomers. In addition, the molecular mechanism behind the possible chiral recognition was discussed based on the experimental and theoretical results of the enantiomeric separation and molecular dynamics studies. © 2022 Elsevier B.V.
Açıklama
Anahtar Kelimeler
Amylose tris(3,5-dimethyphenylcarbamate), Arylalkylazole, Chiralpak AD, Enantioseparation, Molecular modeling and dynamics
Kaynak
Journal of Molecular Structure
WoS Q Değeri
Scopus Q Değeri
Q2
Cilt
1270
