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

Journal of Liquid Chromatography and Related Technologies

Volumn 39, Issue 7, 2016, Pages 346-353

  El Behairy, Mohammed Farrag ^a   El Azzouny, Aida A ^a  

^a NATIONAL RESEARCH CENTRE   (Egypt)

Author keywords

2 pyrazolines; Chiral HPLC; elution order; enantioselective; lux column

Indexed keywords

EID: 84969916889     PISSN: 10826076     EISSN: 1520572X     Source Type: Journal    
DOI: 10.1080/10826076.2016.1159967     Document Type: Article

References (30)

1. Y.Okamoto, ; E.Yashima, Polysaccharide Derivatives for Chromatographic Separation of Enantiomers. Angew. Chem. Int. Ed. 1998, 37 (8), 1020–1043
2. J.Shen, ; Y.Okamoto, Efficient Separation of Enantiomers Using Stereoregular Chiral Polymers. Chem. Rev. 2016, 116 (3), 1094–1138.
3. H.Lorenz, ; A.Seidel-Morgenstern, Processes to Separate Enantiomers. Angew. Chem. Int. Ed. 2014, 53 (5), 1218–1250.
4. E.R.Francotte, Enantioselective Chromatography as a Powerful Alternative for the Preparation of Drug Enantiomers. J. Chromatogr. A 2001, 906 (1–2), 379–397.
5. A.Özdemir, ; M.D.Altıntop, ; Z.A.Kaplancıklı, ; G.Turan-Zitouni, ; G.A.Çiftçi, ; Ş.U.Yıldırım, 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.
6. S.Carradori, ; D.Secci, ; A.Bolasco, ; C.De Monte, ; M.Yáñez, 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.
7. B.Cottineau, ; P.Toto, ; C.Marot, ; A.Pipaud, ; J.Chenault, Synthesis and Hypoglycemic Evaluation of Substituted Pyrazole-4-carboxylic Acids. Bioorg. Med. Chem. Lett. 2002, 12 (16), 2105–2108.
8. S.A.Rostom, ; M.A.Shalaby, ; M.A.El-Demellawy, 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.
9. M.N.Aboul-Enein, ; A.A.El-Azzouny, ; M.I.Attia, ; Y.A.Maklad, ; K.M.Amin, ; M.Abdel-Rehim, ; M.F.El-Behairy, Design and Synthesis of Novel Stiripentol Analogues as Potential Anticonvulsants. Eur. J. Med. Chem. 2012, 47, 360–369.
10. J.K.Chakrabarti, ; R.J.Eggleton, ; P.T.Gallagher, ; J.Harvey, ; T.A.Hicks, ; E.A.Kitchen, ; C.W.Smith, 5-Acyl-3-substituted-benzofuran-2(3H)-ones as Potential Antiinflammatory Agents. J. Med. Chem. 1987, 30 (9), 1663–1668.
11. M.F.El-Behairy, ; T.E.Mazeed, ; A.A.El-Azzouny, ; M.N.Aboul-Enein, 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.
12. E.Akbas, ; I.Berber, Antibacterial and Antifungal Activities of New pyrazolo[3,4-d]pyridazin Derivatives. Eur. J. Med. Chem. 2005, 40 (4), 401–405.
13. R.Cirilli, ; R.Ferretti, ; B.Gallinella, ; L.Turchetto, ; A.Bolasco, ; D.Secci, ; P.Chimenti, ; M.Pierini, ; V.Fares, ; O.Befani, ; F.La Torre, 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.
14. M.Lämmerhofer, Chiral Recognition by Enantioselective Liquid Chromatography: Mechanisms and Modern Chiral Stationary Phases. J. Chromatogr. A 2010, 1217 (6), 814–856
15. Y.Okamoto, ; Y.Kaida, Resolution by High-performance Liquid Chromatography Using Polysaccharide Carbamates and Benzoates as Chiral Stationary Phases. J. Chromatogr. A 1994, 666 (1–2), 403–419
16. T.Wang, ; R.M.Wenslow, 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.
17. H.Y.Aboul-Enein, ; I.Ali, Optimization Strategies for HPLC Enantioseparation of Racemic Drugs Using Polysaccharides and Macrocyclic Glycopeptide Antibiotic Chiral Stationary Phases. Il Farmaco 2002, 57 (7), 513–529.
18. M.Winger, ; M.Christen, ; W.F.van Gunsteren, On the Conformational Properties of Amylose and Cellulose Oligomers in Solution. Int. J. Carbohydr. Chem. 2009, 2009, 1–8.
19. K.Gogaladze, ; L.Chankvetadze, ; M.Tsintsadze, ; T.Farkas, ; B.Chankvetadze, 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.
20. P.Sharma, ; P.Contractor, ; S.Guttikar, ; D.P.Patel, ; P.S.Shrivastav, 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.
21. H.Zhang, ; M.Qian, ; X.Wang, ; X.Wang, ; H.Xu, ; Q.Wang, ; M.Wang, HPLC-MS/MS Enantioseparation of Triazole Fungicides Using Polysaccharide-based Stationary Phases. J. Sep. Sci. 2012, 35 (7), 773–777.
22. S.Ma, ; S.Shen, ; H.Lee, ; M.Eriksson, ; X.Zeng, ; J.Xu, ; K.Fandrick, ; N.Yee, ; C.Senanayake, ; N.Grinberg, 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.
23. B.Chankvetadze, ; C.Yamamoto, ; Y.Okamoto, 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.
24. I.Ali, ; L.Naim, ; A.Ghanem, ; H.Aboulenein, Chiral Separations of Piperidine-2,6-dione Analogues on Chiralpak IA and Chiralpak IB Columns by Using HPLC. Talanta 2006, 69 (4), 1013–1017.
25. B.Chankvetadze, Recent Developments on Polysaccharide-based Chiral Stationary Phases for Liquid-phase Separation of Enantiomers. J. Chromatogr. A 2012, 1269, 26–51.
26. L.Mosiashvili, ; L.Chankvetadze, ; T.Farkas, ; B.Chankvetadze, 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.
27. X.Yang, ; L.Su, ; X.Hou, ; S.Ding, ; W.Xu, ; B.Wang, ; H.Fang, 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.
28. A.Ghanem, 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.
29. H.Y.Aboul-Enein, ; I.Ali, 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.
30. P.S.Bonato, ; L.R.de Abreu, ; C.M.de Gaitani, ; V.L.Lanchote, ; C.Bertucci, 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.