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Molecules 2016, 21(9), 1210; doi:10.3390/molecules21091210

Novel Enantiopure Sigma Receptor Modulators: Quick (Semi-)Preparative Chiral Resolution via HPLC and Absolute Configuration Assignment

1
Department of Drug Sciences, Medicinal Chemistry and Pharmaceutical Technology Section, University of Pavia, Viale Taramelli 12, Pavia 27100, Italy
2
Department of Pharmaceutical Chemistry, University of Vienna, Althanstrasse 14, Vienna 1090, Austria
3
Corden Pharma Switzerland LLC, Eichenweg 1, Liestal 4410, Switzerland
*
Author to whom correspondence should be addressed.
Academic Editors: Claudio Villani and Derek J. McPhee
Received: 20 July 2016 / Revised: 30 August 2016 / Accepted: 6 September 2016 / Published: 10 September 2016
(This article belongs to the Special Issue Chiral Drugs)
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Abstract

The identification of novel pan-sigma receptor (SR) modulators, potentially useful in cancer treatment, represents a new goal of our research. Here, we report on the preparation of novel chiral compounds characterized by a 3-C alkyl chain bridging an aromatic portion to a 4-benzyl-piperidine moiety. All of the studied compounds have been prepared both in racemic and enantiomerically-pure form, with the final aim to address the role of chirality in the SR interaction. To isolate and characterize enantiomeric compounds, high-performance liquid chromatography (HPLC) procedures were set up. A systematic analytical screening, involving several combinations of chiral stationary and mobile phases, allowed us to optimize the analytical resolution and to set up the (semi-)preparative chromatographic conditions. Applying the optimized procedure, the enantiomeric resolution of the studied compounds was successfully achieved, obtaining all of the compounds with an enantiomeric excess higher than 95%. Lastly, the absolute configuration has been empirically assigned to enantiopure compounds, combining the electronic circular dichroism (ECD) technique to the elution order study. View Full-Text
Keywords: sigma receptor (SR) modulators; amylose- and cellulose-derived CSPs; chiral resolution; enantioselective HPLC; electronic circular dichroism (ECD) sigma receptor (SR) modulators; amylose- and cellulose-derived CSPs; chiral resolution; enantioselective HPLC; electronic circular dichroism (ECD)
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This is an open access article distributed under the Creative Commons Attribution License which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited. (CC BY 4.0).

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Rui, M.; Marra, A.; Pace, V.; Juza, M.; Rossi, D.; Collina, S. Novel Enantiopure Sigma Receptor Modulators: Quick (Semi-)Preparative Chiral Resolution via HPLC and Absolute Configuration Assignment. Molecules 2016, 21, 1210.

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