Differentiation between partial agonists and neutral 5-HT(1B) antagonists by chemical modulation of 3-[3-(N,N-dimethylamino)propyl]-4- hydroxy-N-[4-(pyridin-4-yl)phenyl]benzamide (GR-55562)

Journal of Medicinal Chemistry

Volumn 40, Issue 22, 1997, Pages 3542-3550

  Lamothe, Marie ^a   Pauwels, Petrus J ^a   Belliard, Karine ^a   Schambel, Philippe ^a   Halazy, Serge ^a  

^a INSTITUT DE RECHERCHE PIERRE FABRE   (France)

Author keywords

[No Author keywords available]

Indexed keywords

3 (3 DIMETHYLAMINOPROPYL) 4 HYDROXY N [4 (4 PYRIDINYL)PHENYL]BENZAMIDE; 3 [3 (N,N DIMETHYLAMINO)PROP 1 ENYL] 4 METHOXY N [4 (PYRIDIN 4 YL)PHENYL]BENZAMIDE; 3 [3 (N,N DIMETHYLAMINO)PROP 1 YNYL] 4 METHOXY N [4 (PYRIDIN 4 YL)PHENYL]BENZAMIDE; 3 [3 (N,N DIMETHYLAMINO)PROPYL] 4 METHOXY N [4 (PYRIDIN 4 YL)PHENYL]BENZAMIDE; PARTIAL AGONIST; SEROTONIN 1B RECEPTOR; SEROTONIN AGONIST; SEROTONIN ANTAGONIST; UNCLASSIFIED DRUG;

ANIMAL CELL; ARTICLE; DRUG BINDING SITE; DRUG CONFORMATION; DRUG RECEPTOR BINDING; DRUG SYNTHESIS; HUMAN; HUMAN CELL; HYDROGEN BOND; MOLECULAR MODEL; NONHUMAN; RECEPTOR AFFINITY; RECEPTOR INTRINSIC ACTIVITY;

ANIMALS; BENZAMIDES; COS CELLS; DRUG SYNERGISM; MAGNETIC RESONANCE SPECTROSCOPY; MODELS, MOLECULAR; MOLECULAR STRUCTURE; PYRIDINES; RADIOLIGAND ASSAY; RECEPTOR, SEROTONIN, 5-HT1B; RECEPTORS, SEROTONIN; SEROTONIN AGONISTS; SPECTROPHOTOMETRY, INFRARED;

EID: 0030687549     PISSN: 00222623     EISSN: None     Source Type: Journal    
DOI: 10.1021/jm9702948     Document Type: Article

References (28)

1. Glennon, R. A. Serotonin receptors: clinical implications. Neurosci. Biobehav. Rev. 1990, 14, 35-47.
2. Hoyer, D.; Clarke, D. E.; Fozard, J. R.; Hartig, P. R.; Martin, G. R.; Mylechorane, E. J.; Saxena, P. R.; Humphrey, P. P. Inter-national union of pharmacology classification of receptors for 5-hydroxytryptamine (serotonin). Pharmacol. Rev. 1994, 46, 157-203.
3. 1D receptor genes. Trends Pharmacol. Sci. 1992, 13, 152-159.
4. 1Dβ. Proc. Natl. Acad. Sci. U.S.A. 1992, 89, 3630-3634.
5. 1Dβ T355N mutant receptors may involve formation of two hydrogen bonds to asparagine. Mol. Pharmacol. 1996, 49, 198-206.
6. 1B receptors. Nature (London) 1992, 360, 161-163.
7. 355Asn site directed mutagenesis. Biochem. Pharmacol. 1992, 44, 1917-1920.
8. 1D receptor subtypes. Trends Pharmacol. Sci. 1996, 17, 103-105.
9. 1B/1D receptor antagonists. Gen. Pharmacol. 1997, in press.
10. Ferrari, M. D.; Saxena, P. R. On serotonin and migraine: a clinical and pharmacological review. Cephalagia 1993, 13, 151-165.
11. Moskowitz, M. A. Neurogenic versus vascular mechanisms of sumatriptan and ergot alkaloids in migraine. Trends Pharmacol. Sci. 1992, 13, 307-311.
12. 1B/1D antagonists and depression. Exp. Opin. Ther. Pat. 1997, 7, 339-352.
13. Briley, M.; Moret, C. Neurobiological mechanisms involved in antidepressant therapies. Clin. Neuropharmacol. 1993, 16, 387-400.
14. 1B/1D receptor antagonist GR-127935. CNS Drugs Rev. 1996, 2, 415-428.
15. 1Dα receptor sites. Neuropharmacology 1995, 34, 235-237.
16. 1Dβ receptors. Eur. J. Pharmacol. 1996, 324, 365-372.
17. 1Dβ receptors. Eur. J. Pharmacol. 1995, 287, 79-84.
18. 1D receptors; an answer from GTPγS binding studies with stably transfected C6-glial cell lines. Neuropharmacology 1997, 36, 499-512.
19. Mitchell, W. L.; Clitherow, J. W.; Glaxo Group Ltd. Brit. U.K. Pat. Appl. GB 2,276,163; Chem. Abstr. 1995, 122, 9879p.
20. 1D antagonists. J. Med. Chem. 1994, 37, 2253-2257.
21. Sonogashira, K.; Tohda, Y.; Hagihara, N. A convenient synthesis of acetylenes: catalytic substitutions of acetylenic hydrogen with bromoalkenes, iodoarenes and bromopyridines. Tetrahedron Lett. 1975, 4467-4470.
22. Ishikura, M.; Ohta, T.; Terashima, M. A novel synthesis of 4-aryl-and 4-heteroarylpyridines via diethyl(4-pyridyl)borane. Chem. Pharm. Bull. 1985, 33, 4755-4763.
23. Fisher, F. C.; Havinga, E. Thermal and photoinduced deboronations of some pyridine- and benzeneboronate anions. Recl. Trav. Chim. Pays-Bas 1974, 93, 21-24.
24. Chan, K. S.; Zhang, H. Base effect on the cross-coupling of bulky arylboronic acid with halopyridines. Tetrahedron Lett. 1996, 37, 1043-1044.
25. 2-adrenergic receptor. Extending the ternary complex model J. Biol. Chem. 1993, 268, 4625-4636.
26. 1B receptor selectivity for 5-HT terminal autoreceptor activity: an in vivo microdialysis study in the freely-moving guinea-pig. Neuropharmacology 1997, 36, 549-557.
27. 1D receptors. Proc. Br. Pharmacol. Soc. 1996, (Sept. 11-13, University of Dundee), 301P.
28. 14 acid hydrazide. J. Am. Chem. Soc. 1952, 74, 6289-6290.