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Structure and pharmacological studies of the anaesthetic 1-(3-n-butoxypropyl)-4-benzoyloxypiperidin hydrochloride and its complex with β-cyclodextrin in solution. NMR and IR-spectroscopy data

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Abstract

Using different 1D and 2D NMR methods including Nuclear Overhauser effects in the rotating frame the structural features of 1-(3-n-butoxypropyl)-4-benzoyloxypiperidine hydrochloride and its inclusion complex with β-cyclodextrin were investigated in aqueous solution. 1-(3-n-butoxypropyl)-4-benzoyloxypiperidine hydrochloride exists as a mixture of two conformational isomers with axial and equatorial orientation of the benzoyloxy group (ca. 2:1). Both these isomers effectively form inclusion complexes with β-cyclodextrin as host molecule.

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Acknowledgments

The authors acknowledge financial support by Volkswagen Stiftung in the frame of the international focus ‘‘Between Europe and the Orient’’ project I/82033 and Ministry of Education and Science of Kazakhstan project 2/02, October 26 2010.

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Authors and Affiliations

  1. Regional Testing Laboratory Engineering Profile “Structural and Biochemical Materials”, M. Auezov South Kazakhstan State University of MES RK, Tauke Khan Str., 5, 160012, Shymkent, Kazakhstan

    U. Kemelbekov & A. Saipov

  2. Laboratory of Engineering Profile NMR-spectroscopy, Kokshetau State University, Sh. Ualikhanov of MES RK, Kazakhstan Abai Str., 76, 020000, Kokshetau, Kazakhstan

    A. Abdildanova & I. Ospanov

  3. Institut für Chemie und Biochemie, Freie Universität Berlin, Takustrasse 3, 14195, Berlin, Germany

    Y. Luo

  4. Institut für Chemie und Biochemie/Kristallographie, Freie Universität Berlin, Takustrasse 6, 14195, Berlin, Germany

    A. Guskov & W. Saenger

  5. Kazakh National Medical University in the name of S.D. Asfendiyarov, Zhetisu Str., 2, 050012, Almaty, Kazakhstan

    Sh. Imachova, S. Nasyrova & G. Pichkhadze

Authors
  1. U. Kemelbekov
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  2. A. Saipov
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  3. A. Abdildanova
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  4. I. Ospanov
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  5. Y. Luo
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  6. A. Guskov
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  7. W. Saenger
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  8. Sh. Imachova
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  9. S. Nasyrova
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  10. G. Pichkhadze
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Corresponding authors

Correspondence to U. Kemelbekov or G. Pichkhadze.

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Kemelbekov, U., Saipov, A., Abdildanova, A. et al. Structure and pharmacological studies of the anaesthetic 1-(3-n-butoxypropyl)-4-benzoyloxypiperidin hydrochloride and its complex with β-cyclodextrin in solution. NMR and IR-spectroscopy data. J Incl Phenom Macrocycl Chem 77, 249–257 (2013). https://doi.org/10.1007/s10847-012-0239-0

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  • DOI: https://doi.org/10.1007/s10847-012-0239-0

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