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Glucosides of morphine derivatives: synthesis and characterization

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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.

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Authors and Affiliations

  1. Department of Pharmaceutical Chemistry, Semmelweis University, 9. Hogyes Endre u., Budapest, 1092, Hungary

    András Váradi, Dóra Lévai, Gergő Tóth, Péter Horváth, Béla Noszál & Sándor Hosztafi

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  1. András Váradi
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  2. Dóra Lévai
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  3. Gergő Tóth
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  4. Péter Horváth
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  5. Béla Noszál
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  6. Sándor Hosztafi
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Correspondence to András Váradi.

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Váradi, A., Lévai, D., Tóth, G. et al. Glucosides of morphine derivatives: synthesis and characterization. Monatsh Chem 144, 255–262 (2013). https://doi.org/10.1007/s00706-012-0868-4

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  • DOI: https://doi.org/10.1007/s00706-012-0868-4

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