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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Trescot A, Glaser SE, Hansen H, Benyamin R, Patel S, Manchikanti L (2008) Pain Phys 11:S181
Vallejo R, Barkin RL, Wang VC (2011) Pain Phys 14:E343
Smith HS (2011) Clin J Pain 27:824
Váradi A, Gergely A, Béni S, Jankovics P, Noszál B, Hosztafi S (2011) Eur J Pharm Sci 42:65
Mori M, Oguri K, Yoshimura H, Shimomura K, Kamata O, Ueki S (1972) Life Sci 11:525
Yoshimura H, Ida S, Oguri K, Tsukamoto H (1973) Biochem Pharmacol 22:1423
Pasternak GW, Bodnar RJ, Clark JA, Inturrisi CE (1987) Life Sci 41:2845
Paul D, Standifer KM, Inturrisi CE, Pasternak GW (1989) J Pharmacol Exp Ther 251:477
Chen XY, Zhao LM, Zhong DF (2003) Br J Clin Pharmacol 55:570
Matern H, Matern S (1987) Biochim Biophys Acta. Lipids Lipid Metab 921:1
Paibir SG, Soine WH, Thomas DF, Fisher RA (2004) Eur J Drug Metab Pharmacokinet 29:51
Shipkova M, Armstrong VW, Wieland E, Niedmann PD, Schütz E, Brenner-Weiß G, Voihsel M, Braun F, Oellerich M (1999) Br J Pharmacol 126:1075
Tang BK (1990) Pharmacol Ther 46:53
Tang BK, Kalow W, Grey AA (1978) Res Commun Chem Pathol Pharmacol 21:45
Tang BK, Kalow W, Grey AA (1979) Drug Metab Dispos 7:315
Tjornelund J, Hansen SH, Cornett C (1989) Xenobiotica 19:891
Biasutto L, Marotta E, Bradaschia A, Fallica M, Mattarei A, Garbisa S, Zoratti M, Paradisi C (2009) Bioorg Med Chem Lett 19:6721
Hirpara KV, Aggarwal P, Mukherjee AJ, Joshi NJ, Burman AC (2009) Anticancer Agent Med Chem 9:138
Zhao X, Tao X, Wei D, Song Q (2006) Eur J Med Chem 41:1352
Casparis P, Kuhni E, Leinzinger E (1949) Pharm Acta Helv 24:145
Kováč P, Rice KC (1995) Heterocycles 41:697
Lacy C, Sainsbury M (1995) Tetrahedron Lett 36:3949
Stachulski AV, Jenkins GV (1998) Nat Prod Rep 15:173
Stachulski AV, Scheinmann F, Ferguson JR, Law JL, Lumbard KW, Hopkins P, Patel N, Clarke S, Gloyne A, Joel SP (2003) Bioorg Med Chem Lett 13:1207
Arsequell G, Salvatella M, Valencia G, Fernández-Mayoralas A, Fontanella M, Venturi C, Jiménez-Barbero J, Marrón E, Rodríguez RE (2009) J Med Chem 52:2656
Berrang B, Twine CE, Hennessee GL, Carroll FI (1975) Synth Commun 5:231
Brown RT, Carter NE, Lumbard KW, Scheinmann F (1995) Tetrahedron Lett 36:8661
Yoshimura H, Oguri K, Tsukamoto H (1968) Chem Pharm Bull 16:2114
Mertz AAH (1993) Method for synthesizing glucuronides of 4,5-epoxy morphinanes. PCT Int Appl WO1993005057; March 18, 1993
Welsh LH (1954) J Org Chem 19:1409
Bognár R, Lévai A (1973) Acta Chim Acad Sci Hung 77:435
Bosch ME, Sánchez AR, Rojas FS, Ojeda CB (2007) J Pharm Biomed Anal 43:799
Barrett DA, Pawula M, Knaggs RD, Shaw PN (1998) Chromatographia 47:667
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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