5(10→9)abeo-ergoline derivatives: Synthesis, 5-HT(1A)-receptor affinity and selectivity

European Journal of Medicinal Chemistry

Volumn 33, Issue 4, 1998, Pages 279-292

  Mantegani, Sergio ^a   Baumer, Luca ^a   Brambilla, Enzo ^a   Caccia, Carla ^a   Fornaretto, Maria Gioia ^a   McArthur, Robert Albert ^a   Varasi, Mario ^a  

^a PFIZER INC   (United States)

Author keywords

5(10 9)abeo ergoline derivative; 5 HT(1A) receptor ligand; Ergoline derivative; Serotonin; Structure affinity relationship

Indexed keywords

5(10-9)ABEO 6 METHYL 8 BETA HYDROXYMETHYL 9,10 DIDEHYDROERGOLINE; ERGOLINE DERIVATIVE; LYSERGIDE; MESULERGINE; METERGOLINE; UNCLASSIFIED DRUG;

ARTICLE; DRUG RECEPTOR BINDING; DRUG SYNTHESIS; LIGAND BINDING; MOLECULAR RECOGNITION; NEUROTRANSMITTER RELEASE; NONHUMAN; PROTON NUCLEAR MAGNETIC RESONANCE; RECEPTOR AFFINITY; SEROTONINERGIC SYSTEM; STRUCTURE ACTIVITY RELATION;

EID: 0032051970     PISSN: 02235234     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0223-5234(98)80062-7     Document Type: Article

References (38)

1. [1] Ninomiya I., Kiguchi T., in: Brossi A. (Ed.), The Alkaloids: Chemistry and Pharmacology, Vol. 38, Academic Press, San Diego, 1990, pp. 1-156.
2. [2] Stadler P.A., Floss H.G., in: Krosgaard-Larsen P., Christensen S.B., Kofod H. (Eds.), Natural Products and Drugs Development. Munksgaard. Copenhagen. 1984.
3. [3] Fuxe K., Ogren S.O., Agnati L.F., Andersson K.. Kall H., Köhler C., Fredholm B., in: Goldstein M., Calne D.B., Lieberman A., Thorner M.O. (Eds.). Advance in Biochemical and Psychopharmacology, Vol. 23, Raven. New York. 1980, pp. 41-74.
4. [4] Johnston A., File S.E., Pharmacol. Biochem. Behav. 24 (1986) 1457-1470.
5. [5] Hollister L.E., Claghorn J.L., Annu. Rev. Pharmacol. Toxicol. 32 (1993) 165-177.
6. [6] Peroutka S.J., Sleight A., McCarthy R.G., Pierce P.A., Schmidt A.W., Hekmatpanath C.R., Neuropsychiatry 1 (1989) 253-262.
7. [7] Monte A.P., Marona-Lewicka D., Kanthasami A., Sanders-Busch E., Nichols D.E., J. Med. Chem. 38 (1995) 958-966.
8. [8] Fregnan G.B., Glässer A.H., Experentia 24 (1968) 150-153.
9. [9] De Caro G., Il Farmaco 20 (1965) 781-786.
10. [10] Bernardi L., Temperilli A., Experentia 54 (1972) 998-999.
11. [11] Pfeiffer R.F., Neuropharmacol. 8 (1985) 64-69.
12. [12] Hartig P.R., Trends Pharmacol. Sci. 10 (1989) 64-69.
13. [13] Albert P.R., Zhou Q.Y., Van Tol H.H.M., Bunzow J.R., Civelli O., J. Biol. Chem. 256 (1990) 5825-5832.
14. [14] De Vry J., DN & P 9(5) (1996) 270-280.
15. [15] Hibert M.F., Gittos M.W., Middlemiss D.N., Mir A.K., Fozard J.R., J. Med. Chem. 31 (1988) 1087-1093.
16. [16] Hibert M.H., Mir A.K., Fozard J.R., in: Hansch C. (Ed.), Comprehensive Medicinal Chemistry, Pergamon, Oxford, 1990, pp. 567-600.
17. [17] Bernardi L., Elli L., Temperilli A., J. Chem. Soc. Chem. Commun. (1976) 570.
18. [18] Cainelli G., Caglioti L., Barbieri W., Il Farmaco 22 (1967) 456-460.
19. [19] Mantegani S., Arlandini E., Borghi D., Brambilla E., Varasi M., Heterocycl. 45 (1997) 1493-1507.
20. [20] Mantegani S., Brambilla E., Caccia C., Carfagna N WO 95/28403.
21. [21] Fehr T., Stadler A., Hofmann A., Helv. Chim. Acta 53 (1970) 2197-2201.
22. [22] Kr'epelka J., Holubek J., Semonsky M., Collect. Czech. Chem. Commun. 47 (1977) 1209-1215.
23. [23] Hutchins R.O., Kandasamy D., Dux III F., Maryanoff C.A., Rotstein D., Goldsmith B., Burgoyne W., Cistone F., Dalessandro J., Puglis J., J. Org. Chem. 43 (1978) 2259-2267.
24. [24] Bernardi L., Bosisio G., Mantegani S., Sapini O., Temporilli A., Salvati P., Di Salle E., Arcari G., Bianchi G., Arzneim. Forsch. 33 (1983) 1094-1097.
25. [25] Krepelka J., Semonsky M., Collect. Czech. Chem. Comm. 47 (1978) 622-625.
26. [26] Scheider H.R., Stadler P.A., Stütz P., Troxler F., Seres J., Experentia 33 (1977) 1412-1414.
27. [27] SIMES, Società Italiana Medicinali e Sintetici, Swiss Patent 8255/77, 1977.
28. [28] Ward J.S., Fuller R.W., Merritt L., Snoddy H.D., Paschal J.W., Mason N.R., Horng J.S., J. Med. Chem. Chem. 31 (1988) 1512-1519.
29. [29] Bellamy F.D., Ou K., Tetrahedron Lett. 25(8) (1984) 839-842.
30. [30] Milner J.D., Synth. Comm. (1992) 73-82.
31. [31] Greengrass P., Bremner R., Eur. J. Pharmacol. 55 (1979) 323-326.
32. [32] Perry B.D., U'Prichard D.C., Eur. J. Pharmacol. 76 (1981) 461-464.
33. [33] Billard W., Ruperto V., Grosby G., Iorio L., Barnett C.A., Life Sci. 35 (1985) 1885-1893.
34. [34] Creese I., Schneider R., Snyder S.H., Eur. J. Pharmacol. 46 (1977) 377-381.
35. [35] Hall M.D., El Mestikawy S., Emerit M., Pichat L., Hamon M., Gozlan H., J. Neurochem. 44 (1985) 1685-1695.
36. [36] Leysen J.E., Niemegeers C.J.E., van Nueten J.M., Laduron P.M., Mol. Pharmacol. 21 (1981) 301-314.
37. [37] Stoll A., Hofmann A., in: Manske R.H.F., Holmes H.L. (Eds.), The Alkaloids, Vol. 8, Academic Press, New York, 1965, pp. 725-783.
38. [38] Stadler P.A.. Stutz P.A., in: Manske R.H.F., Holmes H.L. (Eds.), The Alkaloids, Vol. 15, Academic Press, New York, 1975, pp. 1-40.