Asian Journal of Research in Chemistry

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Atropisomeric Separation of a 2-Aryl-Imino-N-(2-Aryl)-Thiazoline Compound by Reversed Phase HPLC using Hydroxypropyl-γ-Cyclodextrin


Affiliations
1 Laboratory of Applied Chemistry, Lebanese University, P.O. Box 826, Tripoli, Lebanon
2 Department of Chemistry, University Center of Mascara (29000), Algeria
3 Department of Chemistry, University of Balalmand, P.O. Box 100, Tripoli, Lebanon
     

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The fact that atropisomers of a biologically active compound exhibit different activities has attracted worldwide attention. The pharmacological activity of a chiral molecule can vary from one atropisomer to the other. Therefore, it is essential to separate the different atropisomers in order to be able to carry out the various biological tests; an inevitable step in the drug development process. In this study, the separation of racemic-N-[(2Z)-4-methyl-3-(2- methylphenyl)-1,3-thiazol-2(3H)-ylidene]-N-(2-chlorophenyl)amine to collect its atropisomers has been achieved by HPLC using hydroxypropyl-γ-cyclodextrin (HP-γ-CD) (to obtain chiral molecules) and hexane-propane-2-ol as a mobile phase. The optimum conditions of resolution were established by systematically studying the effect of the mobile phase, the CD concentrations and the time of incubation of the CD-substrate.


Keywords

2-Aryl-Imino-N-(2-aryl)-Thiazoline, Atropisomeric Separation, HP-γ-CD, HPLC.
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  • Atropisomeric Separation of a 2-Aryl-Imino-N-(2-Aryl)-Thiazoline Compound by Reversed Phase HPLC using Hydroxypropyl-γ-Cyclodextrin

Abstract Views: 267  |  PDF Views: 0

Authors

Ahmad Allouch
Laboratory of Applied Chemistry, Lebanese University, P.O. Box 826, Tripoli, Lebanon
Inas EL Hassan
Laboratory of Applied Chemistry, Lebanese University, P.O. Box 826, Tripoli, Lebanon
Abdel Razzak AL Zeine
Laboratory of Applied Chemistry, Lebanese University, P.O. Box 826, Tripoli, Lebanon
Youssef Bakkour
Laboratory of Applied Chemistry, Lebanese University, P.O. Box 826, Tripoli, Lebanon
Mohammad Bouchkara
Department of Chemistry, University Center of Mascara (29000), Algeria
El-Nakat Hanna
Department of Chemistry, University of Balalmand, P.O. Box 100, Tripoli, Lebanon
Fawaz El Omar
Laboratory of Applied Chemistry, Lebanese University, P.O. Box 826, Tripoli, Lebanon

Abstract


The fact that atropisomers of a biologically active compound exhibit different activities has attracted worldwide attention. The pharmacological activity of a chiral molecule can vary from one atropisomer to the other. Therefore, it is essential to separate the different atropisomers in order to be able to carry out the various biological tests; an inevitable step in the drug development process. In this study, the separation of racemic-N-[(2Z)-4-methyl-3-(2- methylphenyl)-1,3-thiazol-2(3H)-ylidene]-N-(2-chlorophenyl)amine to collect its atropisomers has been achieved by HPLC using hydroxypropyl-γ-cyclodextrin (HP-γ-CD) (to obtain chiral molecules) and hexane-propane-2-ol as a mobile phase. The optimum conditions of resolution were established by systematically studying the effect of the mobile phase, the CD concentrations and the time of incubation of the CD-substrate.


Keywords


2-Aryl-Imino-N-(2-aryl)-Thiazoline, Atropisomeric Separation, HP-γ-CD, HPLC.