NMR Investigation of the complexation of (S)-2-isopropyl- 1-(o-nitrophenyl)sulfonyl)aziridine with -cyclodextrin

Authors

  • Assia Keniche Laboratoire de Chimie Organique, Substances Naturelles et Analyses (COSNA). University of Tlemcen. P.O. Box 119 Tlemcen 13000, Algeria.
  • Mohamed Z. Slimani Donostia International Physics Center. San Sebastián, Spain
  • Jose I. Miranda Departamento de Química Orgánica-I. Universidad del País Vasco UPV/EHU. Joxe Mari Korta R&D Center. Avda. Tolosa-72. 20018 San Sebastián, Spain.
  • Jesus M. Aizpurua Departamento de Química Orgánica-I. Universidad del País Vasco UPV/EHU. Joxe Mari Korta R&D Center. Avda. Tolosa-72. 20018 San Sebastián, Spain.
  • Joseph Kajima Mulengi Laboratoire de Chimie Organique, Substances Naturelles et Analyses (COSNA). University of Tlemcen. P.O. Box 119 Tlemcen 13000, Algeria.

DOI:

https://doi.org/10.13171/mjc.2.5.2013.01.12.23

Abstract

 Aziridines are known to undergo hydrolysis in the presence of cyclodextrins, whereas the latter are largely investigated as potential vectors of biologically active compounds. Despite this easy cyclodextrin-induced cleavage of aziridines in aqueous medium, it was of interest to find out a model aziridine derivative that would be sufficiently water-stable and form a stable complex with b-cyclodextrin in aqueous medium, so that it could be used as a reference in future formulations or vectorization work. Among compounds we have investigated, we found out that only (S)-2-isopropyl-1-(o-nitrophenyl)sulfonyl)aziridine complied with the above-mentioned solubility and stability requirements. NMR studies of the inclusion complex of this derivative with b-cyclodextrin provided useful parameters related to the stoichiometry of the complex and the association constant Ka. The geometry of the complex was assessed by 2D-ROESY experiments, suggesting a deep insertion of the aziridine into the cavity of b-cyclodextrin.

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Published

2013-12-01

Issue

Vol. 2 No. 5 (2014)

Section

Organic Chemistry

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