Novel derivatives of 3-(dipropylamino)chroman. Interactions with 5- HT(1A) and D(2A) receptors

Bioorganic and Medicinal Chemistry Letters

Volumn 9, Issue 11, 1999, Pages 1583-1586

  Caldirola, Patrizia ^a,c   Chowdhury, Ratan ^a,d   Unelius, Lena ^b   Mohell, Nina ^b   Hacksell, Uli ^a,e   Johansson, Anette M ^a  

^a UPPSALA UNIVERSITY   (Sweden)

^b Astra Arcus AB   (Sweden)

^c PFIZER INC   (United States)

^d UNIVERSITY OF MELBOURNE   (Australia)

^e ACADIA PHARMACEUTICALS INC   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

CHROMAN DERIVATIVE; DOPAMINE 2 RECEPTOR; PALLADIUM; SEROTONIN 1A RECEPTOR;

ANIMAL CELL; ARTICLE; CATALYSIS; DRUG RECEPTOR BINDING; DRUG STRUCTURE; DRUG SYNTHESIS; LIGAND BINDING; MOUSE; NONHUMAN; RAT; RECEPTOR AFFINITY; STRUCTURE ACTIVITY RELATION;

ANIMALIA;

EID: 0033532647     PISSN: 0960894X     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0960-894X(99)00232-2     Document Type: Article

References (24)

1. a) Thorberg, S.-O., Hall, H., Åkesson, C., Svensson, K., Nilsson, J.L.G. Acta Pharm. Suec. 1987, 24, 169-182. b) Cossery, J.M., Perdicakis, C., Coudert, G., Guillamet, G., Pichat, L. J. Labelled. Comp. Radiopharm. 1987, 25, 833-853. c) 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. 1991, 26, 497-504. d) Podona, T., Guardiola-Lemaître, B., Caignard, D.-H., Adam, G., Pfeiffer, B., Renard, P., Guillaumet, G. J. Med. Chem. 1994, 37, 1779-1793.
2. a) Thorberg, S.-O., Hall, H., Åkesson, C., Svensson, K., Nilsson, J.L.G. Acta Pharm. Suec. 1987, 24, 169-182. b) Cossery, J.M., Perdicakis, C., Coudert, G., Guillamet, G., Pichat, L. J. Labelled. Comp. Radiopharm. 1987, 25, 833-853. c) 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. 1991, 26, 497-504. d) Podona, T., Guardiola-Lemaître, B., Caignard, D.-H., Adam, G., Pfeiffer, B., Renard, P., Guillaumet, G. J. Med. Chem. 1994, 37, 1779-1793.
3. a) Thorberg, S.-O., Hall, H., Åkesson, C., Svensson, K., Nilsson, J.L.G. Acta Pharm. Suec. 1987, 24, 169-182. b) Cossery, J.M., Perdicakis, C., Coudert, G., Guillamet, G., Pichat, L. J. Labelled. Comp. Radiopharm. 1987, 25, 833-853. c) 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. 1991, 26, 497-504. d) Podona, T., Guardiola-Lemaître, B., Caignard, D.-H., Adam, G., Pfeiffer, B., Renard, P., Guillaumet, G. J. Med. Chem. 1994, 37, 1779-1793.
4. a) Thorberg, S.-O., Hall, H., Åkesson, C., Svensson, K., Nilsson, J.L.G. Acta Pharm. Suec. 1987, 24, 169-182. b) Cossery, J.M., Perdicakis, C., Coudert, G., Guillamet, G., Pichat, L. J. Labelled. Comp. Radiopharm. 1987, 25, 833-853. c) 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. 1991, 26, 497-504. d) Podona, T., Guardiola-Lemaître, B., Caignard, D.-H., Adam, G., Pfeiffer, B., Renard, P., Guillaumet, G. J. Med. Chem. 1994, 37, 1779-1793.
5. b) Wise, L.D., Dewald, H.A., Hawkins, E.S., Reynolds, D.M., Heffner, T.G., Meltzer, L.T., Pugsley, T.A. J. Med. Chem. 1988, 31, 688-691.
6. a) Arvidsson, L.-E., Hacksell, U., Nilsson, J.L.G., Hjorth, S., Carlsson, A., Lindberg, P., Sanchez, D., Wikström, H. J. Med. Chem. 1981, 24, 921-923. b) Middlemiss, D.N., Fozard, J.R. Eur. J. Pharmacol. 1983, 90, 151-153.
7. a) Arvidsson, L.-E., Hacksell, U., Nilsson, J.L.G., Hjorth, S., Carlsson, A., Lindberg, P., Sanchez, D., Wikström, H. J. Med. Chem. 1981, 24, 921-923. b) Middlemiss, D.N., Fozard, J.R. Eur. J. Pharmacol. 1983, 90, 151-153.
8. a) McDermed, J.D., McKenzie, G.M., Freeman, H.S. J. Med. Chem. 1979, 19, 547-549. b) Tedesco, J.T., Seeman, P., McDermed, J.D. Mol. Pharmacol. 1979, 16, 369-381.
9. a) McDermed, J.D., McKenzie, G.M., Freeman, H.S. J. Med. Chem. 1979, 19, 547-549. b) Tedesco, J.T., Seeman, P., McDermed, J.D. Mol. Pharmacol. 1979, 16, 369-381.
10. a) Vermue, N.A., Kaptein, B., Tepper, P.G., de Vries, J.B., Horn, A.S. Arch. Int. Pharmacodyn. 1988, 293, 37-56. b) Horn, A.S., Kaptein, B., Vermue, N.A., de Vries, J.B., Mulder, T.B.A. Eur. J. Med. Chem. 1988, 23, 325-328.
11. a) Vermue, N.A., Kaptein, B., Tepper, P.G., de Vries, J.B., Horn, A.S. Arch. Int. Pharmacodyn. 1988, 293, 37-56. b) Horn, A.S., Kaptein, B., Vermue, N.A., de Vries, J.B., Mulder, T.B.A. Eur. J. Med. Chem. 1988, 23, 325-328.
12. a) Hackseil, U.; Liu, Y.; Yu, H.; Vallgårda, J.; Backlund Höök, B.; Johansson, A.M.; Lewander, T. Drug Des. Discovery, 1993, 9, 287-297. b) Hacksell, U.; Johansson, A.M.; Karlén, A.; Svensson, K.; Grol, C.J. In "Chirality and Biological Activity", Eds. H. Frank, B. Holmstedt, and B. Testa, Alan R. Liss, Inc., N.Y., 1989, pp 247-266.
13. a) Hackseil, U.; Liu, Y.; Yu, H.; Vallgårda, J.; Backlund Höök, B.; Johansson, A.M.; Lewander, T. Drug Des. Discovery, 1993, 9, 287-297. b) Hacksell, U.; Johansson, A.M.; Karlén, A.; Svensson, K.; Grol, C.J. In "Chirality and Biological Activity", Eds. H. Frank, B. Holmstedt, and B. Testa, Alan R. Liss, Inc., N.Y., 1989, pp 247-266.
14. Cossery, J.M., Gozlan, H., Spampinato, U., Perdicakis, C., Guillaumet, G., Pichat, L., Hamon, M. Eur. J. Pharmacol. 1987, 140, 143-155.
15. Marot, M., Comoy, C., Viaud, M.C., Rettori, M.C., Pfeiffer, B., Morin-Allory, L., Guillaumet, G. Bioorg. Med. Chem. Lett. 1996, 6, 1077-1082.
16. Andersson, B., Wikström, H., Hallberg, A. Acta Chem. Scand. 1990, 44, 1024-1028.
17. Johansson, L.; Sohn, D.; Thorberg, S.-O.; Jackson, D.M.; Kelder, D.; Larsson, L.-G.; Rényi, L.; Ross, S.B.; Wallsten, C.; Eriksson, H.; Hu, P.-S.; Jerning, E.; Mohell, N.; Westlind-Danielsson, A. J. Pharmacol. Exp. Ther. 1997, 283, 216-225.
18. Chumpradit, S.; Kung, M.-P.; Vessotskie, J.; Foulon, C.; Mu, M.; Kung, H.F. J. Med. Chem. 1994, 37, 4245-4250.
19. Brisander, M., Caldirola, P., Johansson, A.M., Hacksell, U. J. Org. Chem. 1998, 63, 5362-5367.
20. Caldirola, P., Chowdhury, R., Johansson, A.M., Hacksell, U. Organometallics, 1995, 14, 3897-3900.
21. Hedberg, M.H., Linnanen, T., Jansen, J.M., Nordvall, G., Hjorth, S., Unelius, L., Johansson, A.M. J. Med. Chem. 1996, 39, 3503-3513.
22. Hedberg, M.H.; Jansen, J.M.; Nordvall, G.; Hjorth, S.; Unelius, L.; Johansson, A.M. J. Med. Chem. 1996, 39, 3491-3502.
23. 2A receptors, see: Jackson, D.M.; Mohell, N.; Georgiev, J.; Bengtsson, A.; Larsson, L.-G.; Magnusson, O.; Ross, S.B. Naunyn-schmiedeberg's Arch. Pharmacol. 1995, 351, 146-155 and Malmberg, Å.; Jackson, D.M.; Eriksson, A.; Mohell, N. Mol. Pharmacol. 1993, 43, 749-754.
24. 2A receptors, see: Jackson, D.M.; Mohell, N.; Georgiev, J.; Bengtsson, A.; Larsson, L.-G.; Magnusson, O.; Ross, S.B. Naunyn-schmiedeberg's Arch. Pharmacol. 1995, 351, 146-155 and Malmberg, Å.; Jackson, D.M.; Eriksson, A.; Mohell, N. Mol. Pharmacol. 1993, 43, 749-754.