Enantioselective HPLC separation of bioactive C5-chiral 2-pyrazolines on lux amylose-2 and lux cellulose-2: Comparative and mechanistic approaches

References

• Okamoto, Y.; Yashima, E. Polysaccharide Derivatives for Chromatographic Separation of Enantiomers. Angew. Chem. Int. Ed. 1998, 37 (8), 1020–1043
   PubMed Web of Science ®Google Scholar
• Shen, J.; Okamoto, Y. Efficient Separation of Enantiomers Using Stereoregular Chiral Polymers. Chem. Rev. 2016, 116 (3), 1094–1138.
   PubMed Web of Science ®Google Scholar
• Lorenz, H.; Seidel-Morgenstern, A. Processes to Separate Enantiomers. Angew. Chem. Int. Ed. 2014, 53 (5), 1218–1250.
   PubMed Web of Science ®Google Scholar
• Francotte, E. R. Enantioselective Chromatography as a Powerful Alternative for the Preparation of Drug Enantiomers. J. Chromatogr. A 2001, 906 (1–2), 379–397.
   PubMed Web of Science ®Google Scholar
• Özdemir, A.; Altıntop, M. D.; Kaplancıklı, Z. A.; Turan-Zitouni, G.; Çiftçi, G. A.; Yıldırım, Ş. U. Synthesis of 1-acetyl-3-(2-thienyl)-5-aryl-2-pyrazoline Derivatives and Evaluation of Their Anticancer Activity. J. Enzyme Inhib. Med. Chem. 2013, 28 (6), 1221–1227.
   PubMed Web of Science ®Google Scholar
• Carradori, S.; Secci, D.; Bolasco, A.; De Monte, C.; Yáñez, M. Synthesis and Selective Inhibitory Activity Against Human COX-1 of Novel 1-(4-Substituted-thiazol-2-yl)-3,5-di(hetero)aryl-pyrazoline Derivatives. Arch. Pharm. 2012, 345 (12), 973–979.
   Web of Science ®Google Scholar
• Cottineau, B.; Toto, P.; Marot, C.; Pipaud, A.; Chenault, J. Synthesis and Hypoglycemic Evaluation of Substituted Pyrazole-4-carboxylic Acids. Bioorg. Med. Chem. Lett. 2002, 12 (16), 2105–2108.
   PubMed Web of Science ®Google Scholar
• Rostom, S. A.; Shalaby, M. A.; El-Demellawy, M. A. Polysubstituted Pyrazoles, Part 5. Synthesis of New 1-(4-chlorophenyl)-4-hydroxy-1H-pyrazole-3-carboxylic Acid Hydrazide Analogs and Some Derived Ring Systems. A Novel Class of Potential Antitumor and Anti-HCV Agents. Eur. J. Med. Chem. 2003, 38 (11–12), 959–974.
   PubMed Web of Science ®Google Scholar
• Aboul-Enein, M. N.; El-Azzouny, A. A.; Attia, M. I.; Maklad, Y. A.; Amin, K. M.; Abdel-Rehim, M.; El-Behairy, M. F. Design and Synthesis of Novel Stiripentol Analogues as Potential Anticonvulsants. Eur. J. Med. Chem. 2012, 47, 360–369.
   PubMed Web of Science ®Google Scholar
• Chakrabarti, J. K.; Eggleton, R. J.; Gallagher, P. T.; Harvey, J.; Hicks, T. A.; Kitchen, E. A.; Smith, C. W. 5-Acyl-3-substituted-benzofuran-2(3H)-ones as Potential Antiinflammatory Agents. J. Med. Chem. 1987, 30 (9), 1663–1668.
   PubMed Web of Science ®Google Scholar
• El-Behairy, M. F.; Mazeed, T. E.; El-Azzouny, A. A.; Aboul-Enein, M. N. Design, Synthesis and Antibacterial Potential of 5-(benzo[d][1,3]dioxol-5-yl)-3-tert-butyl-1-substituted-4,5-dihydropyrazoles. Saudi Pharm. J. 2015, 23 (2), 202–209.
   PubMed Web of Science ®Google Scholar
• Akbas, E.; Berber, I. Antibacterial and Antifungal Activities of New pyrazolo[3,4-d]pyridazin Derivatives. Eur. J. Med. Chem. 2005, 40 (4), 401–405.
   PubMed Web of Science ®Google Scholar
• Cirilli, R.; Ferretti, R.; Gallinella, B.; Turchetto, L.; Bolasco, A.; Secci, D.; Chimenti, P.; Pierini, M.; Fares, V.; Befani, O.; La Torre, F. Enantiomers of C5-chiral 1-acetyl-3,5-diphenyl-4,5-dihydro-(1H)-pyrazole Derivatives: Analytical and Semipreparative HPLC Separation, Chiroptical Properties, Absolute Configuration, and Inhibitory Activity Against Monoamine Oxidase. Chirality 2004, 16 (9), 625–636.
   PubMed Web of Science ®Google Scholar
• Lämmerhofer, M. Chiral Recognition by Enantioselective Liquid Chromatography: Mechanisms and Modern Chiral Stationary Phases. J. Chromatogr. A 2010, 1217 (6), 814–856
   PubMed Web of Science ®Google Scholar
• Okamoto, Y.; Kaida, Y. Resolution by High-performance Liquid Chromatography Using Polysaccharide Carbamates and Benzoates as Chiral Stationary Phases. J. Chromatogr. A 1994, 666 (1–2), 403–419
   Web of Science ®Google Scholar
• Wang, T.; Wenslow, R. M. Effects of Alcohol Mobile-phase Modifiers on the Structure and Chiral Selectivity of Amylose tris(3,5-dimethylphenylcarbamate) Chiral Stationary Phase. J. Chromatogr. A 2003, 1015 (1–2), 99–110.
   PubMed Web of Science ®Google Scholar
• Aboul-Enein, H. Y.; Ali, I. Optimization Strategies for HPLC Enantioseparation of Racemic Drugs Using Polysaccharides and Macrocyclic Glycopeptide Antibiotic Chiral Stationary Phases. Il Farmaco 2002, 57 (7), 513–529.
   PubMedGoogle Scholar
• Winger, M.; Christen, M.; van Gunsteren, W. F. On the Conformational Properties of Amylose and Cellulose Oligomers in Solution. Int. J. Carbohydr. Chem. 2009, 2009, 1–8.
   Google Scholar
• Gogaladze, K.; Chankvetadze, L.; Tsintsadze, M.; Farkas, T.; Chankvetadze, B. Effect of Basic and Acidic Additives on the Separation of Some Basic Drug Enantiomers on Polysaccharide-Based Chiral Columns with Acetonitrile as Mobile Phase. Chirality 2015, 27 (3), 228–234.
   PubMed Web of Science ®Google Scholar
• Sharma, P.; Contractor, P.; Guttikar, S.; Patel, D. P.; Shrivastav, P. S. Development of a Sensitive and Rapid Method for Quantitation of (S)-(−)- and (R)-(+)-metoprolol in Human Plasma by Chiral LC–ESI–MS/MS. J. Pharm. Anal. 2014, 4 (1), 63–79.
   Google Scholar
• Zhang, H.; Qian, M.; Wang, X.; Wang, X.; Xu, H.; Wang, Q.; Wang, M. HPLC-MS/MS Enantioseparation of Triazole Fungicides Using Polysaccharide-based Stationary Phases. J. Sep. Sci. 2012, 35 (7), 773–777.
   PubMed Web of Science ®Google Scholar
• Ma, S.; Shen, S.; Lee, H.; Eriksson, M.; Zeng, X.; Xu, J.; Fandrick, K.; Yee, N.; Senanayake, C.; Grinberg, N. Mechanistic Studies on the Chiral Recognition of Polysaccharide-based Chiral Stationary Phases Using Liquid Chromatography and Vibrational Circular Dichroism. J. Chromatogr. A 2009, 1216 (18), 3784–3793.
   PubMed Web of Science ®Google Scholar
• Chankvetadze, B.; Yamamoto, C.; Okamoto, Y. Enantioseparation of Selected Chiral Sulfoxides Using Polysaccharide-type Chiral Stationary Phases and Polar Organic, Polar Aqueous–organic and Normal-phase Eluents. J. Chromatogr. A 2001, 922 (1–2), 127–137.
   PubMed Web of Science ®Google Scholar
• Ali, I.; Naim, L.; Ghanem, A.; Aboulenein, H. Chiral Separations of Piperidine-2,6-dione Analogues on Chiralpak IA and Chiralpak IB Columns by Using HPLC. Talanta 2006, 69 (4), 1013–1017.
   PubMed Web of Science ®Google Scholar
• Chankvetadze, B. Recent Developments on Polysaccharide-based Chiral Stationary Phases for Liquid-phase Separation of Enantiomers. J. Chromatogr. A 2012, 1269, 26–51.
   PubMed Web of Science ®Google Scholar
• Mosiashvili, L.; Chankvetadze, L.; Farkas, T.; Chankvetadze, B. On the Effect of Basic and Acidic Additives on the Separation of the Enantiomers of Some Basic Drugs with Polysaccharide-based Chiral Selectors and Polar Organic Mobile Phases. J. Chromatogr. A 2013, 1317, 167–174.
   PubMed Web of Science ®Google Scholar
• Yang, X.; Su, L.; Hou, X.; Ding, S.; Xu, W.; Wang, B.; Fang, H. High-performance Liquid Chromatographic Enantioseparation of 3,5-disubstituted Hydantoins Analogs and Temperature-induced Reversals of Elution Orders on a Polysaccharide-based Chiral Stationary Phase. J. Chromatogr. A 2014, 1355, 291–295.
   PubMed Web of Science ®Google Scholar
• Ghanem, A. True and False Reversal of the Elution Order of Barbiturates on a Bonded Cellulose-based Chiral Stationary Phase. J. Chromatogr. A 2006, 1132 (1–2), 329–332.
   PubMed Web of Science ®Google Scholar
• Aboul-Enein, H. Y.; Ali, I. Studies on the Effect of Alcohols on the Chiral Discrimination Mechanisms of Amylose Stationary Phase on the Enantioseparation of Nebivolol by HPLC. J. Biochem. Biophys. Methods 2001, 48 (2), 175–188.
   PubMedGoogle Scholar
• Bonato, P. S.; de Abreu, L. R.; de Gaitani, C. M.; Lanchote, V. L.; Bertucci, C. Enantioselective HPLC Analysis of Propafenone and of Its Main Metabolites Using Polysaccharide and Protein-based Chiral Stationary Phases. Biomed. Chromatogr. 2000, 14 (4), 227–233.
   PubMed Web of Science ®Google Scholar