Synthesis and structure-activity relationships of new arylpiperazines: Para substitution with electron-withdrawing groups decrease binding to 5-HT1A and D2A receptors

European Journal of Medicinal Chemistry

Volumn 37, Issue 6, 2002, Pages 503-510

  Santana, Lourdes ^a   Uriarte, Eugenio ^a   Fall, Yagamare ^b   Teijeira, Marta ^b   Terán, Carmen ^b   García Martínez, Emilia ^b   Tolf, Bo Ragnar ^c  

^a UNIVERSITY OF SANTIAGO DE COMPOSTELA   (Spain)

^b UNIVERSITY OF VIGO   (Spain)

^c Research and Development at Scania Technical Centre   (Sweden)

Author keywords

5 HT1A receptors; Coumarins; D2A receptors; Disubstituted piperazines

Indexed keywords

COUMARIN; PHENYL GROUP; PIPERAZINE DERIVATIVE; RADIOLIGAND; SEROTONIN 1A RECEPTOR; SEROTONIN 2A RECEPTOR;

ANIMAL CELL; ANIMAL TISSUE; ARTICLE; BINDING ASSAY; CONTROLLED STUDY; DRUG ACTIVITY; DRUG RECEPTOR BINDING; DRUG STRUCTURE; ELECTRON TRANSPORT; ELECTRONICS; LIGAND BINDING; LIPOPHILICITY; MOLECULAR SIZE; MOUSE; NONHUMAN; RAT; RECEPTOR AFFINITY; STEREOSPECIFICITY; STRUCTURE ACTIVITY RELATION; SUBSTITUTION REACTION;

8-HYDROXY-2-(DI-N-PROPYLAMINO)TETRALIN; ANIMALS; COUMARINS; DRUG DESIGN; ELECTRONS; FIBROBLASTS; HIPPOCAMPUS; HUMANS; INDICATORS AND REAGENTS; MICE; PIPERAZINES; RACLOPRIDE; RADIOLIGAND ASSAY; RATS; RATS, SPRAGUE-DAWLEY; RECEPTORS, DOPAMINE D2; RECEPTORS, SEROTONIN; RECEPTORS, SEROTONIN, 5-HT1; STRUCTURE-ACTIVITY RELATIONSHIP;

EID: 0036592242     PISSN: 02235234     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0223-5234(02)01357-0     Document Type: Article

References (34)

1. Baldesarini R.J., Tarazi F.I. Harv. Rev. Psychiatry. 3:1996;301-325.
2. Glenon R.A., Westkaemper R.B., Bartyzel P. Peroutka S.J., Medicinal Chemistry of Serotonergic Agents. 1991;19-64 Wiley-Liss, New York.
3. Seeman P. Synapse. 1:1987;133-135.
4. Tamminga J.M. Coyle J.T., Enna S.J., Neuroleptics: Neurochemical, Biochemical and Clinical Perspectives. 1983;281-295 Raven, New York.
5. Krupp P., Barnes P. Br. J. Psychiatry. 160:1992;38-41.
6. Carlsson A. Usdin E., Bunney W.E., Pre-and Postsynaptic Receptors. 1975;49-65 Marcel Dekker, New York.
7. Soudijn W., van Wijngaarden I. Olivier B., van Wijngaarden I., Soudijn W., Serotonin Receptors and Their Ligands. 1997;327-361 Elsevier, Amsterdam.
8. van Wijngaarden I., Tulp M.T.M., Soudijn W. Eur. J. Pharmacol. Mol. Pharmacol. Sect. 188:1990;301-312.
9. Martínez-Esparza J., Oficialdegui A.-M., Pérez-Silanes S., Heras B., Orús L., Palop J.-A., Lasheras B., Roca J., Mourelle M., Bosch A., Del Castillo J.-C., Tordera R., Del Río J., Monge A. J. Med. Chem. 44:2001;418-428.
10. van Steen B.J., Wijngaarden I., Tulp M., Soudjin W. J. Med. Chem. 36:1993;2751-2760.
11. Glenon R.A. Drug Dev. Res. 26:1992;247-251.
12. McMillen B.A., Mattiace L.A. J. Neural Transm. 57:1983;255-265.
13. Wadenberg M.-L., Cortizo L., Ahlenius S. Pharmacol. Biochem. Behav. 24:1986;1409-1415.
14. Reitz A.B., Bennet D.J., Blum P.S., Codd E.E., Maryanoff C.A., Ortegon M.E., Renzi M.J., Scott M.K., Shank R.P., Vaught J.L. J. Med. Chem. 37:1994;1060-1062.
15. Homan E.J., Copinga S., Elström L., van der Veen T., Hallema J.-P., Unelius L., Johanson R., Wikström H., Grol C.J. Bioorg. Med. Chem. 6:1998;2111-2126.
16. Birch A.M., Bradley P.A., Gill J.C., Kerrigan F., Needham P.L. J. Med. Chem. 42:1999;3342-3355.
17. Martin E.G., Elgin R.J. Jr., Mathiasen J.R., Davis C.B., Kesslick J.M., Baldy W.J., Shank R.P., Di Stefano D.L., Fedde C.L., Scott M.K. J. Med. Chem. 32:1989;1052-1056.
18. Ransom R.W., Asarch K.B., Shih J.C. J. Neurochem. 46:1986;68-75.
19. Perrone R., Berardi F., Colabufo N.A., Leopoldo M., Tortorella V. J. Med. Chem. 42:1999;490-496.
20. Glennon R.A., Naiman N.A., Lyon R.A. J. Med. Chem. 31:1988;1968-1971.
21. Banno K., Fujioka T., Kikuchi T., Oshiro Y., Hiyama T., Nakagawa K. Chem. Phar. Bull. 36:1988;4377-4388.
22. Jaen J.C., Wise L.D., Heffner T.G., Pugsley T.A., Meltzer L.T. J. Med. Chem. 34:1991;248-256.
23. Santana L., Teran C., Uriarte E., Fall Y., Unellius L., Tolf B.-R. Bioorg. Med. Chem. Lett. 8:1988;3567-3570.
24. Jaen J.C., Wise L.D., Heffner T.G., Pugsley T.A., Meltzer L.T. J. Med. Chem. 31:1988;1621-1625.
25. Buckle D.R., Cantello B.C.C., Smith H., Spicer B.A. J. Med. Chem. 18:1975;391-394.
26. Xie L., Takeuchi Y., Cosentino L.M., Lee K.-H. J. Med. Chem. 42:1999;2662-2672.
27. Ahluwalia V.K., Kumar D. Indian J. Chem. 15B:1977;945-946.
28. Fall Y., Teran C., Teijeira M., Santana L., Uriarte E. Synthesis. 5:2000;643-645.
29. Hedberg M.H., Johanson A.M., Nordvall G., Yliniemelä A., Li H.B., Martin A.R., Hjort S., Unelius L., Sundel S., Hacksell U. J. Med. Chem. 38:1995;647-658.
30. Malmberg A., Jackson D.M., Eriksson A., Mohell N. Mol. Pharmacol. 43:1993;749-754.
31. López-Rodríguez M.L., Rosado M.L., Benhamú B., Morcillo M.J., Sanz A.M., Orensanz L., Beneitez M.E., Fuentes J.A., Manzanares J. J. Med. Chem. 39:1996;4439-4450.
32. Mokrosz M.J., Kowalski P., Kowalska T., Majka Z., Duszynska B., Bojarski A.J., Fruzinski A., Karolak-Wojciechowska J., Wesolowska A., Klodzinska A., Tatarczynska E., Chojnacka-Wojcik E. Arch. Pharm. Pharm. Med. Chem. 332:1999;373-378.
33. Caliendo G., Fiorino F., Grieco P., Perissuti E., Santagada V., Severino B., Bruni G., Romeo M.R. Bioorg. Med. Chem. 8:2000;533-538.
34. Munson P.J., Rodbard D. Anal. Biochem. 107:1980;220-239.