Advertisement

The structure and pharmacological properties of the 4-acetoxy-1-(2-ethoxyethyl)-4-phenylpiperidine inclusion complex with β-cyclodextrin

  • R. A. Sharipov
  • K. S. Sharapov
  • U. S. Kemelbekov
  • V. A. VolynkinEmail author
  • V. K. Yu
  • V. T. Panyushkin
  • K. D. Praliev
Original Article

Abstract

Inclusion complex of 4-acetoxy-1-(2-ethoxyethyl)-4-phenylpiperidine with β-cyclodextrin was synthesized. Composition (1:2) and the structure of the complex were confirmed by NMR spectroscopy and thermal analysis. The results of pharmacological studies showed that the compound is of interest for in-depth testing, because of its deeper and more prolonged conduction anaesthesia, terminal (superficial) and infiltration anaesthesia along with less acute toxicity compared to the reference preparations.

Keywords

Cyclodextrin Anaesthetic Pharmacological properties ROESY 

References

  1. 1.
    Laurence, D.R., Bennett, P.N., Morris, J.B.: Clin. Pharmacol. 8th edn. Churchill Livingstone, New York (1997)Google Scholar
  2. 2.
    Kemelbekov, U., Luo, Y., Orynbekova, Z., Rustembekov Zh., Haag, R., Saenger, W., Praliyev, K.: IR, UV and NMR studies of β-cyclodextrin inclusion complexes of kazcaine and prosidol bases. J. Incl. Phenom. Macrocycl. Chem. 69, 181–190 (2011)CrossRefGoogle Scholar
  3. 3.
    Yu, V.K., Nagimova, A.D., Praliev, K.D., Shin, S.N., De Kempe, N.: Synthesis, antibacterial, and analgesic activity of 1-(2-ethoxyethyl)-4-hydroxy(acyloxy)-piperidine-4-carboxylic acids. Pharm. Chem. J. 36, 282–284 (2002)CrossRefGoogle Scholar
  4. 4.
    Kemelbekov, U.S., Hagenbach, A., Lentz, D., Imachova Sh.O., Pichkhadze, G.M., Rustembekov, Zh.I., Beketov, K.M., Praliev, K.D., Gabdulkhakov, A., Guskov, A., Saenger, W.: Pharmacology and structures of the free base of the anaesthetic kazcaine and its complex with β-cyclodextrin. J. Incl. Phenom. Macrocycl. Chem. 68, 323–330 (2010)CrossRefGoogle Scholar
  5. 5.
    Praliev, K.D., Isin, Zh., Yu, V.K., Tarakov, S.A., Bosyakov, Yu.G., Utepbergenova, R.K., Shin, S.N., Kadyrova, D.M.: Hydrochloride of 1-(2-ethoxyethyl)-4-ethynyl-4-benzoyloxy-piperidine possesses anesthetic activity. Patent Ru. 1704415 (1996)Google Scholar
  6. 6.
    Kaldybekova, G.M., Kemelbekov, U.S., Abdildanova, A.A., Praliev, K.D., Volynkin, V.A., Nasyrova S.R., Imashova, Sh.O., Pichkhadze, G.M.: Preparation of an inclusion complex of 1-(3-n-butoxypropyl)-4-vinilacetylen-4-benzoyloxypiperidine with β-cyclodextrin and its local anestetic activity. Pharm. Chem. J. 48, 196–200 (2014)CrossRefGoogle Scholar
  7. 7.
    Dodziuk, H.: Molecules with holes—cyclodextrins. In: Dodziuk, H. (ed) Cyclodextrins and their complexes: chemistry, analytical methods, applications. Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim (2006)CrossRefGoogle Scholar
  8. 8.
    Schneider, H.-J., Hacket, F., Rüdiger, V., Ikeda, H.: NMR studies of cyclodextrins and cyclodextrin complexes. Chem. Rev. 98, 1755–1785 (1998)CrossRefGoogle Scholar
  9. 9.
    Crini, G.: A history of cyclodextrins. Chem. Rev. 114, 10940–10975 (2014)CrossRefGoogle Scholar
  10. 10.
    Bettinetti, G., Novák Cs., Sorrenti, M.: Thermal and structural characterization of commercial α-, β-, and γ-cyclodextrins. J. Therm. Anal. Calorim. 68, 517–529 (2002)CrossRefGoogle Scholar
  11. 11.
    Sambasevam, K.P., Mohamad, S., Sarih, N.M., Ismail, N.A.: Synthesis and characterization of the inclusion complex of β-cyclodextrin and azomethine. Int. J. Mol. Sci. 14, 3671–3682 (2013)CrossRefGoogle Scholar
  12. 12.
    Roik, N.V., Belyakova, L.A.: IR spectroscopy, X-ray diffraction and thermal analysis studies of solid “β-cyclodextrin—para-aminobenzoic acid” inclusion complex. Phys. Chem. Solid State 12, 168–173 (2011)Google Scholar
  13. 13.
    Pessine F.B.T., Calderini A., Alexandrino, G.L.: Review: cyclodextrin inclusion complexes probed by NMR techniques. In: Kim, D.H. (ed) Magnetic resonance spectroscopy, InTech. (2012) http://www.intechopen.com/books/magneticresonance-spectroscopy/review-study-of-inclusion-complexes-with-cyclodextrins-by-mrs
  14. 14.
    Sharapov K.S., Volynkin V.A., Panyushkin V.T.: On the structure of the β-cyclodextrin inclusion complex with 4-acetoxy-1-(2-ethoxyethyl)-4-phenylpiperidine. Russ. Chem. Bull. 65, 834–839 (2016)CrossRefGoogle Scholar
  15. 15.
    Heyes, S.J., Nigel, J., Clayden, L., Dobson, C.M.: 13C-CP/MAS NMR studies of the cyclomalto-oligosaccharide (cyclodextrin) hydrates. Carbohydr. Res. 233, 1–14 (1992)CrossRefGoogle Scholar
  16. 16.
    Quevauviller, A.: Local anaesthetics in experimental methods for comparing local anaesthetic activity. In: International Encyclopedia of Pharmacology and Therapeutics. Pergamon Press, Fayetteville, pp. 291–318 (1971)Google Scholar
  17. 17.
    Camougis, G., Takman, B.H.: Methods for evaluating local anesthetics. In: Schwartz, A. (ed) Methods in pharmacology. Appleton Century Crofts, New York, pp. 1–40. (1971)CrossRefGoogle Scholar
  18. 18.
    Kemelbekov, U., Saipov, A., Abdildanova, A., Ospanov, I., Luo, Y., Guskov, A., Saenger, W., Imachova Sh., Nasyrova, S., Pichkhadze, G.: Structure and pharmacological studies of the anesthetic 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)CrossRefGoogle Scholar

Copyright information

© Springer Science+Business Media Dordrecht 2016

Authors and Affiliations

  1. 1.Kokshetau Technical Institute of the Kazakhstan Ministry of Emergency SituationsKokshetauKazakhstan
  2. 2.Kuban State UniversityKrasnodarRussia
  3. 3.National Centre for Expertise of Medicines, Medical Devices and Medical EquipmentAlmatyKazakhstan
  4. 4.A.B. Bekturov Institute of Chemical SciencesAlmatyKazakhstan

Personalised recommendations