Chiral separation of novel iminonaringenin derivatives

Meriem Bouanini; Nasser Belboukhari; J Carlos Menéndez; Khaled Sekkoum; Abdelkarim Cheriti; Hassan Y Aboul-Enein

doi:10.1002/chir.22812

Chiral separation of novel iminonaringenin derivatives

Chirality. 2018 Apr;30(4):484-490. doi: 10.1002/chir.22812. Epub 2018 Jan 15.

Authors

Meriem Bouanini¹, Nasser Belboukhari¹, J Carlos Menéndez², Khaled Sekkoum¹, Abdelkarim Cheriti³, Hassan Y Aboul-Enein⁴

Affiliations

¹ Bioactive Molecules and Chiral Separation Laboratory, Faculty of Science and Technology, University of Bechar, Bechar, Algeria.
² Pharmaceutical and Organic Chemistry Department, School of Pharmacy, University of Madrid (Complutense), Madrid, Spain.
³ Phytochemistry and Organic Synthesis Laboratory, Faculty of Science and Technology, University of Bechar, Bechar, Algeria.
⁴ Pharmaceutical and Medicinal Chemistry Department, Pharmaceutical and Drug Industries Research Division, National Research Center, Cairo, Egypt.

PMID: 29334407
DOI: 10.1002/chir.22812

Abstract

A series of 4-iminonaringenin derivatives 2-6 have been prepared in good overall yields from a condensation reaction between naringenin and primary amines. The structures of all products were confirmed by ultraviolet, infrared, proton nuclear magnetic resonance, and carbon-13 nuclear magnetic resonance spectroscopic techniques. These derivatives were analyzed by high-performance liquid chromatography using polysaccharide-based chiral stationary phases, namely, Chiralpak IB and Chiralcel OD, using various mobile phases. 2-Propanol showed a high enantioselectivity for naringin and its derivatives using achiral column containing immobilized polysaccharides (Chiralpak IB).

Keywords: Chiralcel OD; Chiralpak IB; HPLC; N- 4-iminonaringenins; naringin, naringenin; polysaccharide-based chiral stationary phases.