Monatshefte für Chemie - Chemical Monthly

, Volume 144, Issue 2, pp 255–262

Glucosides of morphine derivatives: synthesis and characterization

Authors

    • Department of Pharmaceutical ChemistrySemmelweis University
  • Dóra Lévai
    • Department of Pharmaceutical ChemistrySemmelweis University
  • Gergő Tóth
    • Department of Pharmaceutical ChemistrySemmelweis University
  • Péter Horváth
    • Department of Pharmaceutical ChemistrySemmelweis University
  • Béla Noszál
    • Department of Pharmaceutical ChemistrySemmelweis University
  • Sándor Hosztafi
    • Department of Pharmaceutical ChemistrySemmelweis University
Original Paper

DOI: 10.1007/s00706-012-0868-4

Cite this article as:
Váradi, A., Lévai, D., Tóth, G. et al. Monatsh Chem (2013) 144: 255. doi:10.1007/s00706-012-0868-4

Abstract

Six 3-O- and 6-O-glucosides of morphine and codeine derivatives were synthesized by means of glucosylation with acetobromo-α-d-glucose. O-Glucosylation at C6 was carried out by the Koenigs-Knorr method, whereas the 3-O-glycoside of morphine was synthesized directly upon stirring morphine with acetobromo-α-d-glucose and aqueous sodium hydroxide in acetone. Complete 1H and 13C NMR assignments are presented for each synthesized compound based on one- and two-dimensional homo- and heteronuclear NMR techniques. Circular dichroism, ultraviolet absorbance, and high-resolution mass spectroscopy data ensure identification and structural characterization of the O-glucoside conjugates. The synthesized glucoside conjugates are potential analgesics; the presented spectral and chromatographic data are useful references for various analytical and metabolic studies including samples of biological origin.

Graphical Abstract

https://static-content.springer.com/image/art%3A10.1007%2Fs00706-012-0868-4/MediaObjects/706_2012_868_Figa_HTML.gif

Keywords

MorphineGlucosideNMR spectroscopyAlkaloidsHigh-pressure liquid chromatography

Copyright information

© Springer-Verlag Wien 2012