Fentanyl derivatives bearing aliphatic alkaneguanidinium moieties: A new series of hybrid molecules with significant binding affinity for μ-opioid receptors and I2-imidazoline binding sites

Bioorganic and Medicinal Chemistry Letters

Volumn 14, Issue 2, 2004, Pages 491-493

  Dardonville, Christophe ^a   Jagerovic, Nadine ^a   Callado, Luis F ^b   Meana, J Javier ^b  

^a INSTITUTO DE QUÍMICA MÉDICA   (Spain)

^b UNIVERSITY OF THE BASQUE COUNTRY UPV EHU   (Spain)

Author keywords

Alkane guanidine; Dual acting drug; Human brain; I2 Imidazoline binding site affinity; Opioid tolerance; Opioid withdrawal; opioid affinity

Indexed keywords

FENTANYL; FENTANYL DERIVATIVE; IDAZOXAN; IMIDAZOLINE I2 RECEPTOR; MU OPIATE RECEPTOR; N [1 (2 PHENETHYL) 4 PIPERIDYL] N (GUANIDINOPROPYL)PROPANAMIDE; PROPIONAMIDE DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; BINDING AFFINITY; BINDING SITE; BRAIN MEMBRANE; DRUG SYNTHESIS; HUMAN; HUMAN TISSUE; PREFRONTAL CORTEX; RECEPTOR BINDING;

EID: 0346729860     PISSN: 0960894X     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.bmcl.2003.10.048     Document Type: Article

References (16)

1. Boronat M.A., Olmos G., Garcia-Sevilla J.A. Ann. N. Y. Acad. Sci. 881:1999;359.
2. Fairbanks C.A., Posthumus I.J., Kitto K.F., Stone L.S., Wilcox G.L. Pain. 84:2000;13.
3. Sanchez-Blazquez P., Boronat M.A., Olmos G., Garcia-Sevilla J.A., Garzon J. Br. J. Pharmacol. 130:2000;146.
4. Boronat M.A., Olmos G., Garcia-Sevilla J.A. Br. J. Pharmacol. 125:1998;175.
5. Ruiz-Durantez E., Torrecilla M., Pineda J., Ugedo L. Br. J. Pharmacol. 138:2003;494.
6. Reis D.J., Regunathan S. Trends Pharmacol. Sci. 21:2000;187.
7. Morgan A.D., Campbell U.C., Fons R.D., Carroll M.E. Pharmacol. Biochem. Behav. 72:2002;873.
8. Aricioglu-Kartal F., Regunathan S. Life Sci. 71:2002;1695.
9. Essawi M.Y.H. Bull. Fac. Pharm. (Cairo Univ.). 28:1990;11.
10. Montero A., Goya P., Jagerovic N., Callado L.F., Meana J.J., Giron R., Goicoechea C., Martin M.I. Bioorg. Med. Chem. 10:2002;1009.
11. Dardonville C., Rozas I., Callado L.F., Meana J.J. Bioorg. Med. Chem. 10:2002;1525.
12. Using only 1.5 equiv of propionic anhydride and DMAP cat. made the purification easier than the method previously described.
13. Poss M.A., Iwanowicz E., Reid J.A., Lin J., Gu Z. Tetrahedron Lett. 33:1992;5933.
14. +MS m/ z 486.5 [M+H]; 243.9 [(M+2H), 100%].
15. Miralles A., Olmos G., Sastre M., Barturen F., Martin I., Garcia-Sevilla J.A. J. Pharmacol. Exp. Ther. 264:1993;1187.
16. Gabilondo A.M., Meana J.J., Barturen F., Sastre M., Garcia-Sevilla J.A. Psychopharmacology (Berl). 115:1994;135.