Synthesis and in vitro structure-activity relationship of 13-tert- butyl-ergoline derivatives as 5-HT(1A) receptor ligands

European Journal of Medicinal Chemistry

Volumn 32, Issue 10, 1997, Pages 795-804

  Mantegani, S ^a   Brambilla, E ^a   Caccia, C ^a   Fornaretto, M G ^a   Mc Arthur, R A ^a   Varasi, M ^a  

^a PFIZER INC   (United States)

Author keywords

13 tert butyl ergoline; 5 HT(1A) affinity; Ergoline derivative; Selectivity

Indexed keywords

BUSPIRONE; CABERGOLINE; ERGOLINE DERIVATIVE; PERGOLIDE MESILATE; SEROTONIN 1A RECEPTOR;

ARTICLE; DRUG SYNTHESIS; LIGAND BINDING; PARKINSONISM; RECEPTOR AFFINITY; RECEPTOR BINDING; RECEPTOR POTENTIAL; STRUCTURE ACTIVITY RELATION;

EID: 0030783531     PISSN: 02235234     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0223-5234(99)80065-8     Document Type: Article

References (39)

1. a) Ninomiya I, Kiguchi T (1990) Ergot alkaloids. In: The Alkaloids: Chemistry and Pharmacology (Brossi A, ed) Academic Press Inc, San Diego, Vol 38, 1-156
2. b) Stadler PA, Floss HG (1984) Natural Products and Drugs Development (Krosgaard-Larsen P, Christensen SB, Kofod H, eds) Munksgaard, Copenhagen
3. Fuxe K, Ögren SO, Agnati LF, Andersson K, Kall H, Köhler C, Fredholm B (1980) Central monoamine synapses as sites of action of ergot derivatives. In: Advances in Biochemical and Psychopharmacology (Goldstein M, Calne DB, Lieberman A, Thorner MO, eds) Raven Press, New York, Vol 23, 41-74
4. a) Riederer P, Solic E, Konradi C, Kornhuber J, Beckmann H, Dietl M, Moll G, Hebenstreit G, Thorner MO, Vance MJ, Stoof JC, Tilders FJ, Petcher TJ (1989) The role of brain dopamine. In: Basic and Clinical Aspects of Neuroscience (Flückiger E, Muller EE, Thorner MO, eds) Springer-Verlag, Berlin-Heidelberg, Vol 3
5. b) Piccoli F, Riuggeri RM (1995) J Neural Transm 45, 187-195
6. c) Rabey JM (1995) J Neural Transm 45, 213-224
7. a) Fozard JR, Saxena PR (1991) Serotonin: Molecular Biology, Receptors and Functional Effects, Birkauser Verlag, Basel
8. b) Peroutka SJ (1991) Receptor Biochemistry and Methodology; Serotonin Receptor Subtypes - Basic and Clinical Aspects, Wiley-Liss, New York, Vol 15
9. Fuller W, Clemens JA, Kornfeld EC, Snoddy HD, Smalstig EB, Bach NJ (1979) Life Sci 24, 375-379
10. a) Ferrari C, di Salle E, Persiani S, Piscitelli G, Strolin Benedetti M (1995) Drug of Today 31 (8), 589-596
11. b) Rains C, Bryson MH, Fitton A (1995) Drugs 49 (2), 255-279
12. c) Brambilla E, Di Salle E, Briatico G, Mantegani S, Temperilli A (1989) Eur J Med Chem 24, 421-423
13. a) Fregnan GB, Glässer AH (1968) Experentia 24, 150-153
14. b) De Caro G (1965) Il Farmaco Ed Sci 20, 781-786
15. c) Bernardi I, Temperilli A (1972) Experentia 54, 998-999
16. a) Jansen I, Blackburn T, Eriksen K, Edvinsson L (1991) Pharmacol Toxicol 68, 8-13
17. b) Garbrecht WL, Marzoni G, Witten KR, Cohen ML (1988) J Med Chem 31, 444-448
18. a) Traber J, Glaser T (1987) Trends Pharmacol Sci 8, 432-437
19. b) Taylor DP, Allen LE, Becher JA, Crane M, Hyslop DK, Riblet LA (1984) Drug Dev Res 4, 95-108
20. a) Dunn C (1991) Serotonin Report (unpublished)
21. b) Ennis MD (1993) Curr Opin Invest Drugs 2, 271-279
22. c) Hoyer D (1994) Pharmacol Rev 46, 157-243
23. a) Mc Dermod JD, Freeman HS, Ferris RM (1978) Catecholamines: Basic and Clinical Frontiers (Usdin E, Kopin IJ, Barchas J, eds) Pergamon, New York, 586-570
24. b) Tedesco JL, Seeman P, Mc Dermod JD (1979) Mol Pharmacol 16, 369-374
25. c) Nilsson JGL, Svensson K, Hjorth S, Carlsson A (1985) J Med Chem 28, 215-221
26. Mantegani S, Brambilla E, Caccia C, Carfagna N (July 4, 1995) US Patent 5, 430, 031
27. Mantegani S, unpublished observations
28. a) Euerby MR, Waigh RD (1984) J Chem Soc Chem Comm 127-128
29. b) Back T, Baron D, Yang K (1993) JOC 58, 2407-2413
30. a) Schneider HR, Stadler PA, Stütz P, Troxler F, Seres J (1977) Experentia 33, 1412-1414
31. b) SIMES (Società Italiana Medicinali e Sintetici) (July 5, 1977) Swiss Patent 8255/77
32. Hughes LD (1992) The Mitsunobu reaction. In: Organic Reaction (Leo A Paquette, ed) John Wiley, New York, Vol 42, 335-655
33. Troxler F, Hofmann A (1957) Helv Chim Acta 40, 2160-2162
34. Greengrass P, Bremner R (1979) Eur J Pharmacol 55, 323-326
35. Perry BD, U'Prichard DC (1981) Eur J Pharmacol 76, 461-464
36. Billard W, Ruperto V, Grosby G, Iorio L, Barnett CA (1985) Life Sci 35, 1885-1893
37. Creese I, Schneider R, Snyder SH (1977) Eur J Pharmacol 46, 377-381
38. Hall MD, El Mestikawy S, Emerit M, Pichat L, Hamon M, Gozlan H (1985) J Neurochem 44, 1685-1695
39. Leysen JE, Niemegeers CJE, van Nueten JM, Laduron PM (1981) Mol Pharmacol 21, 301-314