An efficient method has been proposed for the preparation of a series of 3-O-acyl derivatives of naloxone. The features of the steric structure and NMR spectra are discussed. Pharmaceutical investigation has shown the promise within the synthesized compounds of creating opiate receptor antagonist compounds with prolonged action.
Similar content being viewed by others
References
T. Tucker, A. Ritter, C. Maher, and H. Jackson, Drug Alcohol Rev., 23, 299 (2004).
A. I. Minko and I. V. Linskii, Narkologiya, EKSMO, Moscow (2004).
E. M. Krupitsky, E. E. Zvartau, D. V. Masalov, M. V. Tsoi, A. M. Burakov, V. Y. Egorova, T. Y. Didenko, T. N. Romanova, E. B. Ivanova, A. Y. Bespalov, E. V. Verbitskaya, N. G. Neznanov, A. Y. Grinenko, C. P. O’Brien, and G. E. Woody, J. Subst. Abuse Treat., 26, 285 (2004).
M. A. Sullivan, F. Garawi, A. Bisaga, S. D. Comer, K. Carpenter, W. N. Raby, S. J. Anen, A. C. Brooks, H. Jiang, E. Akerele, and E. V. Nunes, Drug Alcohol Depend., 91, 289 (2007).
B. E. Fuller, T. Rieckmann, D. McCarty, K. W. Smith, and H. Levine, J. Subst. Abuse Treat., 28, 273 (2005).
H. M. Pettinati, C. P. O'Brien, A. R. Rabinowitz, S. P. Wortman, D. W. Oslin, K. M. Kampman, and C. A. Dackis, J. Clin. Psychopharmacol., 26, 610 (2006).
D. W. Oslin, W. H. Berrettini, and C. P. O’Brien, Addict. Biol., 11, 397 (2006).
S. G. Kuznetsov, S. M. Chigareva, and S. M. Ramsh, in: Results in Science and Technology. Organic Chemistry [in Russian], Vol. 1, VINITI, Moscow (1991), p. 25.
N. S. Zefirov, V. A. Palyulin, and E. E. Dashevskaya, J. Phys. Org. Chem., 3, 147 (1990).
Yu. V. Zefirov, Kristallografiya, 42, 936 (1997).
L. L. Lachmann, R. H. Reiner, E. Shami, and W. Spector, DE 232192 (1973). http://ep.espacenet.com
B. J. Aungst and M. A. Hussain, US Pat. 4673679 (1987). http://ep.espacenet.com
M. A. Hussain, C. A. Koval, M. J. Myers, E. G. Shami, and E. Shefter, J. Pharm. Sci., 76, 356 (1987).
R. T. Bartus, D. F. Emerich, J. Hotz, M. Blaustein, R. L. Dean, B. Perdomo, and A. S. Basile, Neuropsychopharmacology, 28, 1973 (2003).
H. R. Kranzler, D. R. Wesson, and L. Billot, Alcohol Clin. Exp. Res., 28, 1051 (2004).
B. A. Johnson, N. Ait-Daoud, H. J. Aubin, W. Van Den Brink, R. Guzzetta, J. Loewy, B. Silverman, and E. Ehrich, Alcohol Clin. Exp. Res., 28, 1356 (2004).
H. T. Ngo, R. J. Tait, D. E. Arnold-Reed, and G. K. Hulse, Prog. Neuropsychopharmacol. Biol. Psychiatry, 31, 605 (2007).
C. A. G. Haasnoot, F. A. A. M. de Leeuw, and C. Altona, Tetrahedron, 36, 2783 (1980).
European Pharmacopoeia, 5th Edition (2007). http://online.pheur.org/entry.htm
G. M. Sheldrick, SHELXTL PLUS. PC Version. A System of Computer Programs for the Determination of Crystal Structure from X-ray Diffraction Data, Rev. 5.1 (1998).
N. P. Kravkov, Essentials of Pharmacology [in Russian], State Publishing House, Moscow, (1933).
H. H. Meyer and R. Gotlieb, Experimental Pharmacology as a Basis for Therapeutics [in Russian], Vol. 1, State Medical Publishing House, Moscow (1940).
V. P. Fisenko (editor), Guidelines for Experimental (Preclinical) Study of Novel Pharmacological Materials [in Russian], IIa Remedium, Moscow (2000), p. 162.
S. N. Lapach, A. V. Chubenko, and P. N. Babich, Statistical Methods in Medico-Biological Studies using Excel [in Russian], Morion, Kiev (2000).
Author information
Authors and Affiliations
Corresponding author
Additional information
Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 4, pp. 519–534, April, 2009.
Rights and permissions
About this article
Cite this article
Ukrainets, I.V., Tkach, A.A., Gorokhova, O.V. et al. Studies of 3-O-acyl derivatives of naloxone as its potential prodrugs. Chem Heterocycl Comp 45, 405–416 (2009). https://doi.org/10.1007/s10593-009-0278-7
Received:
Published:
Issue Date:
DOI: https://doi.org/10.1007/s10593-009-0278-7