Substituted 3-amino and/or 3-aminomethyl-3,4-dihydro-2H-1-benzopyrans: Synthesis and biological activity

Bioorganic and Medicinal Chemistry

Volumn 8, Issue 3, 2000, Pages 483-495

  Comoy, Corinne ^a   Guérin, Virginie ^a   Pfeiffer, Bruno ^b   Rettori, Marie Claire ^c   Renard, Pierre ^b   Guillaumet, Gérald ^a  

^a UNIVERSITÉ D'ORLÉANS   (France)

^b ADIR   (France)

^c INSTITUT DE RECHERCHES INTERNATIONALES SERVIER   (France)

Author keywords

[No Author keywords available]

Indexed keywords

2 DIBUTYLAMINO 8 HYDROXYTETRALIN; 3 AMINOMETHYL 3,4 DIHYDRO 2H 1 BENZOPYRAN DERIVATIVE; BENZOPYRAN DERIVATIVE; BUSPIRONE; DOPAMINE 2 RECEPTOR; ERGOT DERIVATIVE; KETANSERIN; N METHYLMESOLERGINE; RACLOPRIDE; RITANSERIN; SEROTONIN 1A RECEPTOR; SEROTONIN 2A RECEPTOR; TRITIUM; UNCLASSIFIED DRUG;

ANIMAL TISSUE; BINDING COMPETITION; BRAIN; CATTLE; CONTROLLED STUDY; DRUG POTENCY; DRUG RECEPTOR BINDING; DRUG SELECTIVITY; DRUG SYNTHESIS; MASS SPECTROMETRY; NONHUMAN; PROTON NUCLEAR MAGNETIC RESONANCE; RADIOASSAY; RECEPTOR AFFINITY; REVIEW; SWINE;

EID: 0342751311     PISSN: 09680896     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0968-0896(99)00311-9     Document Type: Article

References (63)

1. Peroutka S.J., Snyder S.H. J. Pharmacol. Exp. Ther. 216:1981;142.
2. Eison M.S. Psychopathology. 17:1984;37.
3. Johnston A.L., File S.E. Pharmacol. Biochem. Behav. 24:1986;1467.
4. Norman A.B., Battaglia G., Morrow A.L., Creese I. Eur. J. Pharmacol. 16:1984;461.
5. Hollister L.E., Claghorn J.L. Annu. Rev. Pharmacol. Toxicol. 32:1993;165.
6. Peroutka S.J., Sleight A.J., MacCarthy R.G., Pierce P.A., Schmidt A.W., Hekmatpanah C.R. Neuropsychiatry. 1:1989;253.
7. Ferrari, M. D.; Saxena, P. R. In Comprehensive Medicinal Chemistry; Hansch, C., Ed.; Pergamon: Oxford, 1990; pp 567-600.
8. Wilkinson, L. O.; Dourish, C. T. In Serotonin Receptor Subtypes: Basic and Clinical Aspects; Peroutka, S. J., Ed.; John Wiley and Sons: New York, 1991; pp 147-210.
9. Sleight, A. J.; Pierce, P. A.; Schmidt, A. W.; Kekmatpanah, C. R.; Peroutka, S. J. In Serotonin Receptor Subtypes: Basic and Clinical Aspects; Peroutka, S. J., Ed.; John Wiley and Sons: New York, 1991; pp 211-277.
10. Hoyer D., Clarke D.E., Fozard J.R., Hartig P.R., Martin G.R., Mylecharane E.J., Saxena P.R., Humphrey P.P.A. Pharmacol. Rev. 46:1994;157.
11. Saudou F., Hen R. Neurochem. Int. 25:1994;503.
12. Martin G.R., Humphrey P.P.A. Neuropharmacology. 33:1994;261.
13. Chilmonczyck Z. J. Pharm. Pharmacol. 47:1995;791.
14. Lucas J.J., Hen R. Trends Pharmacol. Sci. 16:1995;246.
15. Peroutka S.J. CNS Drugs. 4(Suppl. 1):1994;18.
16. Hoyer D., Martin G.R. Behav. Brain Res. 73:1996;263.
17. Rasmussen, K.; Rocco, V. P In Annual Reports in Medicinal Chemistry; Bristol, J. A., Ed.; Academic: New York, 1995; Vol. 30, pp 1-9.
18. Broekkamp C.L.E., Leysen D., Peeters B.W.M., Pinder R.M. J. Med. Chem. 38:1995;4615.
19. Artigas F. Trends Pharmacol. Sci. 14:1993;262.
20. Blier P., Montigny C. Trends Pharmacol. Sci. 15:1994;220.
21. Barrett J.E., Vanvover K.E. Psychopharmacology. 112:1993;1.
22. Hamon M. Trends Pharmacol. Sci. 15:1994;36.
23. Kastenholz K.V., Crismon M.L. Clin. Pharm. 3:1984;600.
24. Traber J., Glaser T. Trends Pharmacol. Sci. 8:1987;432.
25. Harrington T.M., Albrecht D., David D., Downey D.B., Freeman A., Miller E., Norton J., Roth D., Rumbo N., Shehan D., Weart W. Drug. Invest. 1:1989;1.
26. Richardson, B. P.; Hoyer, D. In Serotonin: From Cells Biology to Pharmacology and Therapeutics; Paoletti, R.; Ed.; Dordrecht: Kluwer, 1990; pp 265-276.
27. Böhm C., Placchi P., Stallone F., Gammans R.E., Alms D.E., Shrotriya R.C., Robinson D.S.A. J. Clin. Psychopharmacol. 10(Suppl. 3):1990;38.
28. Böhm C., Robinson D.S., Gammans R.E., Shrotriya R.C., Alms D.E., Leroy A., Placchi M. J. Clin. Psychopharmacol. 10(Suppl. 3):1990;47.
29. Robinson D.S., Rickels K., Feghner J., Fabre L.F., Gammans R.E., Shrotriya R.C., Alms D.R., Andary J.J., Messina M.E. J. Clin. Psychopharmacol. 10(Suppl. 3):1990;67.
30. Taylor D.P., Moon S.L. Neuropeptides. 19:1991;15.
31. Leysen J.E., Awouters F., Kennis L., Laduron P.M., Vandenberg J., Janssen P.A. J. Life Sci. 28:1981;1015.
32. Fozard J.R. J. Cardiovasc. Pharmacol. 4:1982;829.
33. Awouters F. Drugs Dev. Res. 6:1985;263.
34. Frishman W.H., Huberfeld S., Okin S., Wang Y.H., Kumar A., Shareef B. J. Clin. Pharmacol. 35:1995;541.
35. Arriaga, F.; Leitao, J.; Padua, J.; Ruiz, I.; Tropa, J.; Souza, M. P.; Mills, F. J.; Gelders, Y. In C. I. P. N., Congress Puerto Rico, 1986; p. 174.
36. Da Rosa Davis J.M., Scharpley A.L., Cowen P.J. Psychopharmacol. 108:1992;387.
37. Millan, M. J.; Brocco, M. In Anxiety: Neurobiology, Clinic and Therapeutic Pespectives; Hamon, M.; Ollat, H.; Thiebot, M. H., Eds.; INSERM/John Libbey Eurotext: Paris, 1993; pp 153-154.
38. Albinsson A., Björk A., Svartengren J., Klint T., Andersson G. Eur. J. Med. Pharmacol. 261:1994;285.
39. Yevich J.P., New J.S., Smith D.W., Lobeck W., Catt J.D., Minielli J.L., Eison M.S., Taylor D.P., Riblet L.A., Temple D.L. J. Med. Chem. 29:1986;359.
40. Norman M.H., Ridgon G.C., Navas F., Cooper B.R. J. Med. Chem. 37:1994;2252.
41. Hrib N.J., Jurcak J.G., Burgher K.L., Conway P.G., Hartmann H.B., Keerman L.L., Roehr J.E., Woods A.T. J. Med. Chem. 37:1994;2308.
42. Comoy C., Benarab A., Monteil A., Leinot M., Massingham R., Guillaumet G. Med. Chem. Res. 6:1996;392.
43. Al Neirabeyeh M., Reynaud D., Podona T., Ou L., Perdicakis C., Coudert G., Guillaumet G., Pichat L., Gharib A., Sarda N. Eur. J. Med. Chem. 26:1991;497.
44. Guillaumet, G.; Viaud, M. C.; Renard, P.; Adam, G.; Caignard, D. H.; Guardiola- Lemaître, B.; Rettori, M. C. Eur. Pat. Appl. EP 671, 397, 1995; Chem. Abst. 1995, 123, 313767s.
45. Guillaumet, G.; Coudert, G.; Podona, T.; Guardiola-Lemaître, B.; Renard, P.; Adam, G.; Caignard, D. H. Eur. Pat. Appl. EP 571, 243, 1993; Chem. Abst. 1994, 120, 217283a.
46. Podona T., Guardiola-Lemaître B., Caignard D.H., Adam G., Pfeiffer B., Renard P., Guillaumet G. J. Med. Chem. 37:1994;1779.
47. Comoy C., Marot C., Podona T., Baudin M.L., Morin-Allory L., Guillaumet G., Pfeiffer B., Caignard D.H., Renard P., Rettori M.C., Adam G., Guardiola- Lemaître B. J. Med. Chem. 39:1996;4285.
48. Marot C., Comoy C., Viaud M.C., Rettori M.C., Pfeiffer B., Morin-Allory L., Guillaumet G. Bioorg. Med. Chem. Lett. 6:1996;1077.
49. Williard P.G., Fryhle C.B. Tetrahedron Lett. 3731:1980;21.
50. Boyé S., Pfeiffer B., Renard P., Rettori M.C., Guillaumet G., Viaud M.C. Bioorg. Med. Chem. 7:1999;335.
51. McKillop A., Fiaud J.C., Hug R.P. Tetrahedron. 30:1974;1379.
52. Lane C.F. Aldrichimica Acta. 10:1977;41.
53. 2:MeOH, 99:1).
54. Comoy C., Guillaumet G. Heterocycl. Commun. 2:1996;25.
55. Hoyer D., Engel G., Kalkman H.O. Eur. J. Pharmacol. 118:1985;13.
56. Leysen J.E., Niemegeers C.J.E., Van Nueten J.M., Laduron P.M. Mol. Pharmacol. 21:1982;301.
57. Sanders-Busch E., Breading M. J. Pharmacol. Exp. 247:1988;1.
58. Köhler C., Hall H., Ogren S.V., Gawell L. Biochem. Pharmacol. 34:1985;2251.
59. Reader T.A., Boulianne S., Molina Holdago E., Dewan K.M. Biochem. Pharmacol. 40:1990;1739.
60. Andersson G., Albinsson A., Björk A., Svartengren J. CNS Drug Reviews. 2:1996;363.
61. Van Wijngaarden I., Tulp M.Th. M., Soudijn W. Eur. J. Pharmacol. Mol. Pharm. 188:1990;301.
62. Wainscott D.B., Cohen M.L., Schenck K.W., Audri J.E. Mol. Pharm. 43:1993;419.
63. Rettori, M. C., unpublished results.