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

• Published in: Chirality (New York, N.Y.) N.Y.), 2024-03, Vol.36 (3), p.e23659-n/a
• Main Authors: Ali, Imran, Nabti, Rekia, Belboukhari, Nasser, Sekkoum, Khaled, Zaid, Mohammed El Amin, Kraim, Khairedine, ALOthman, Zeid A., Locatelli, Marcello, Demir, Ersin
• Format: Article
• Language: English
• Subjects: Amylose; Anticoagulants; calcium channel antagonists; Cellulose; chiral separation; Chromatography; comparison; Enantiomers; Ethanol; Flavanones; Hexanes; HPLC; Methanol; Naringenin; Polymers; Separation; SFC; Stereoisomerism; Thiourea; Thiourea derivatives
• ISSN: 0899-0042; 1520-636X
• DOI: 10.1002/chir.23659

Due to a great demand for amylose and cellulose polymeric chromatographic chiral columns, the enantiomeric separation of thiourea derivatives of naringenin was achieved on the different amylose (Chiralpak‐IB) and cellulose chiral (Chiralcel‐OJ and Chiralcel‐OD‐3R) columns with varied chromatographic conditions. The isocratic mobile phases used were ethanol and methanol, where ethanol/hexane and methanol/hexane were used as gradient mode and were prepared in volume/volume relation. The separation and resolution factors for all the enantiomers were in the range of 1.25 to 3.47 and 0.48 to 1.75, respectively. The enantiomeric resolution was obtained within 12 min making fast separation. The docking studies confirmed the chiral recognition mechanisms with binding affinities in the range of −4.7 to −5.7 kcal/mol. The reported compounds have good anticoagulant activities and may be used as anticoagulants in the future. Besides, chiral separation is fast and is useful for enantiomeric separation in any laboratory in the world. Facile synthesis of new anticoagulant compounds, their chiral separation, and anticoagulant activity determination.