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Direct Enantiomeric Resolution of Seventeen Racemic 1,4-Dihydropyridine-Based Hexahydroquinoline Derivatives by HPLC

1
Shenyang Pharmaceutical University, Shenyang 110016, China
2
Department of Pharmaceutical Chemistry, Faculty of Pharmacy, Hacettepe University, Sıhhiye, Ankara 06100, Turkey
*
Authors to whom correspondence should be addressed.
Int. J. Mol. Sci. 2019, 20(10), 2513; https://doi.org/10.3390/ijms20102513
Received: 27 March 2019 / Revised: 17 May 2019 / Accepted: 19 May 2019 / Published: 22 May 2019
(This article belongs to the Section Molecular Pharmacology)
1,4-Dihydropyridine (DHP) scaffold holds an outstanding position with its versatile pharmacological properties among all heterocyclic compounds. Although most of the commercially available DHPs are marketed as a racemic mixture, the chiral center at C-4 can lead to even opposite pharmacological activities between the enantiomers. In the present study, enantioseparation of seventeen DHP structural analogues, consisting of either pharmacologically active or newly synthesized derivatives, (M2-4, MD5, HM2, HM10, CE5, N11, N10, N7, M11, MC6-8, MC13, MD23, and 42IIP) by high-performance liquid chromatography was investigated using immobilized polysaccharide-based chiral stationary phase, Chiralpak IC column. Due to the solvent versatility of the covalently immobilized chiral stationary phase in enantiomer separation, multiple elution modes including standard normal phase, nonstandard mobile phase, and reversed phase were used to expand the possibility to find the optimum enantioselective conditions for the tested analytes. Under appropriate separation conditions, complete enantiomeric separation was obtained for nearly all compounds except MC6-8 and MC13 which contained two chiral centers. Additionally, the effects of the polar modifier, the additive, and column temperature on the chiral recognition were evaluated. The thermodynamic parameters calculated according to the linear van’t Hoff equation indicated that the chiral separations in this study were enthalpy-driven or entropy-driven. Some parameters of method validation such as linearity, limit of quantitation, and repeatability were also measured for all studied compounds to prove the reliability of the method. View Full-Text
Keywords: 1,4-dihydropyridine; hexahydroquinoline; enantioseparation; Chiralpak IC column; high-performance liquid chromatography 1,4-dihydropyridine; hexahydroquinoline; enantioseparation; Chiralpak IC column; high-performance liquid chromatography
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MDPI and ACS Style

Sun, J.; Gözde Gündüz, M.; Zhang, J.; Yu, J.; Guo, X. Direct Enantiomeric Resolution of Seventeen Racemic 1,4-Dihydropyridine-Based Hexahydroquinoline Derivatives by HPLC. Int. J. Mol. Sci. 2019, 20, 2513. https://doi.org/10.3390/ijms20102513

AMA Style

Sun J, Gözde Gündüz M, Zhang J, Yu J, Guo X. Direct Enantiomeric Resolution of Seventeen Racemic 1,4-Dihydropyridine-Based Hexahydroquinoline Derivatives by HPLC. International Journal of Molecular Sciences. 2019; 20(10):2513. https://doi.org/10.3390/ijms20102513

Chicago/Turabian Style

Sun, Jiayi; Gözde Gündüz, Miyase; Zhang, Junyuan; Yu, Jia; Guo, Xingjie. 2019. "Direct Enantiomeric Resolution of Seventeen Racemic 1,4-Dihydropyridine-Based Hexahydroquinoline Derivatives by HPLC" Int. J. Mol. Sci. 20, no. 10: 2513. https://doi.org/10.3390/ijms20102513

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