Synthesis, enantioseparation, and absolute configuration assignment of iminoflavans by chiral high‐performance liquid chromatography combined with online chiroptical detection

Abstract

Four racemic iminoflavan derivatives were synthesized by simple condensation at C-4 position of flavanone. All new compounds were characterized by using ultraviolet-visible, infrared, and nuclear magnetic resonance spectroscopic techniques. A chiral chromatographic analysis of racemic mixtures was performed by direct chiral high-performance liquid chromatography using Chiralcel R OD-H as chiral stationary phase, and online-coupled with electronic circular dichroism detector. The correlation of experimental electronic circular dichroism traces with quantum chemical electronic circular dichroism calculations run with time-dependent density functional theory made it possible to elucidate the absolute configuration for each enantiomer, and to establish the elution order.

Enantioseparation and modeling study of selected chiral pharmaceuticals on a commercialized phenylcarbamate-β-cyclodextrin column using polar organic mode

“…Rabeprazole sodium was United States Pharmacopoeia (USP) reference standard (Rockville, USA). Imino avane derivatives were synthesized as described earlier [31,32]. The structure of investigated compounds is depicted in Fig.…”

Enantiomeric separation of thiourea derivatives of naringenin on amylose and cellulose polymeric chromatographic chiral columns

“…For many years, our research laboratory was directed toward organic synthesis, the study of the biological activities of the synthesized compounds and their chiral separation using different chromatographic methods. [28][29][30][31][32][33][34][35][36][37][38][39][40][41][42][43] Finally, a new bioactive compound was synthesized. The synthesis was carried out in two steps, that is, by producing an intermediate compound (I) followed by adding isothiocyanate as a key element.…”

“…For many years, our research laboratory was directed toward organic synthesis, the study of the biological activities of the synthesized compounds and their chiral separation using different chromatographic methods 28–43 . Finally, a new bioactive compound was synthesized.…”

Chiral Analysis of Sertaconazole by HPLC Method on Polysaccharide Derivatives

“…Over the last decade, many analytical and preparative chromatographic and electrophoretic methods (mainly HPLC and capillary electrophoresis (CE)) have been developed to study the biological action and activity of enantiomeric drugs. Among the methods currently used to achieve chiral separation of racemic mixtures, high-resolution chromatographic systems based on chiral stationary phases (CSPs) (direct methods) are more rapid and suitable for racemic mixtures [14][15][16][17].…”