New 5-HT1A receptor ligands containing a N′-cyanoisonicotinamidine nucleus: Synthesis and in vitro pharmacological evaluation

Bioorganic and Medicinal Chemistry Letters

Volumn 20, Issue 9, 2010, Pages 2978-2982

  Fiorino, Ferdinando ^a   Severino, Beatrice ^a   De Angelis, Francesca ^a   Perissutti, Elisa ^a   Magli, Elisa ^a   Frecentese, Francesco ^a   Esposito, Antonella ^a   Massarelli, Paola ^b   Nencini, Cristina ^b   Santagada, Vincenzo ^a   Caliendo, Giuseppe ^a  

^a UNIVERSITY OF NAPLES FEDERICO II   (Italy)

^b UNIVERSITY OF SIENA   (Italy)

Author keywords

5 HT1a receptor ligands; Arylpiperazines derivatives; N Cyanoisonicotinamidine nucleus

Indexed keywords

ALPHA 1 ADRENERGIC RECEPTOR; ALPHA 2 ADRENERGIC RECEPTOR; DOPAMINE 1 RECEPTOR; DOPAMINE 2 RECEPTOR; N' CYANO N [3 [4 (PYRIDIN 2 YL)PIPERAZIN 1 YL]PROPYL]ISONICOTINAMIDINE; NICOTINAMIDE DERIVATIVE; SEROTONIN 1A RECEPTOR; SEROTONIN 2A RECEPTOR; SEROTONIN 2C RECEPTOR; UNCLASSIFIED DRUG;

ARTICLE; BINDING AFFINITY; DRUG ACTIVITY; DRUG STRUCTURE; DRUG SYNTHESIS; IN VITRO STUDY; MENTAL DISEASE; RECEPTOR AFFINITY;

AMIDINES; ANTIPSYCHOTIC AGENTS; DRUG EVALUATION, PRECLINICAL; LIGANDS; NIACINAMIDE; RECEPTOR, SEROTONIN, 5-HT1A; STRUCTURE-ACTIVITY RELATIONSHIP;

EID: 77950857616     PISSN: 0960894X     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.bmcl.2010.02.106     Document Type: Article

References (42)

1. Den Boer J.A., Bosker F.J., and Slaap B.R. Human Psychopharmacol. 15 (2000) 315
2. Baumgarten H.G., and Gother M. Handb. Exp. Pharmacol. Vol. 1 (1997), Springer, Berlin
3. Martin G.R., Eglen R.M., Hoyer D., Hamblin M.W., and Yocca F. Ann. N.Y. Acad. Sci (1998)
4. Barnes N.M., and Sharp T. Neuropharmacology 38 (1999) 1083
5. Hoyer D., Hannon J.P., and Martin G.R. Pharmacol., Biochem. Behav. 71 (2002) 533
6. Clement Y., and Chapouthier G. Neurosci. Biobehav. Rev. 22 (1998) 623
7. Olivier B., van Wijngaarden I., and Soudjin W. Serotonin Receptors and Their Ligands (1997), Elsevier, The Netherlands
8. Olivier B., Soudjin W., and van Wijngaarden I. Prog. Drug Res. 52 (1999) 103
9. Lopez-Rodriguez M.L., Ayala D., Benhamu B., Morcillo M.J., and Viso A. Curr. Med. Chem. 9 (2002) 443
10. Rickels K., Derivan A., Kunz N., Pallay A., and Schweizer E. J. Clin. Psychopharmacol. 16 (1996) 212
11. Lee C.H., Oh J.I., Park H.D., Kim H.J., Park T.K., Kim J.S., Hong C.Y., Lee S.J., Ahn K.H., and Kim Y.Z. Arch. Pharmacol. Res. 22 (1999) 157
12. Schwartz P.J., Turner E.H., Garcia-Borreguero D., Sedway J., Vetticad R.G., Wehr T.A., Murphy D.L., and Rosenthal N.E. Psychiatry Res. 86 (1999) 9
13. Peglion J.L., Goument B., Despaux N., Charlot V., Giraud H., Nisole C., Newman-Tancredi A., Dekeyne A., Bertrand M., Genissel P., and Millan J. J. Med. Chem. 45 (2002) 165
14. Bikker J.A., Trump-Kallmeyer S., and Humblet S. J. Med. Chem. 41 (1998) 2911
15. Trump-Kallmeyer S., Hoflack J., Bruinvels A., and Hibert M. J. Med. Chem. 35 (1992) 3448
16. Pessoa-Mahana H., Araya-Maturana R., Saitz C.B., and Pessoa-Mahana C.D. Mini-Rev. Med. Chem. 3 (2003) 77
17. Lopez-Rodriguez M.L., Morcillo M.J., Rovat T.K., Fernandez E., Vicente B., Sanz A.M., Hernandez M., and Orensanz L. J. Med. Chem. 42 (1999) 36
18. Caliendo G., Di Carlo R., Meli R., Perissutti E., Santagada V., Silipo C., and Vittoria A. Eur. J. Med. Chem. 28 (1993) 969
19. Caliendo G., Di Carlo R., Greco G., Meli R., Novellino E., Perissutti E., and Santagada V. Eur. J. Med. Chem. 30 (1995) 77
20. Caliendo G., Greco G., Grieco P., Novellino E., Perissutti E., Santagada V., Barbarulo D., Esposito E., and De Blasi A. Eur. J. Med. Chem. 31 (1996) 207
21. Caliendo G., Fiorino F., Grieco P., Perissutti E., Santagada V., Albrizio S., Spadola L., Bruni G., and Romeo M.R. Eur. J. Med. Chem 34 (1999) 719
22. Caliendo G., Fiorino F., Greco P., Perissutti E., Santagada V., Severino B., Bruni G., and Romano M.R. Bioorg. Med. Chem. 8 (2000) 533
23. Caliendo G., Fiorino F., Perissutti E., Severino B., Gessi S., Cattabriga E., Borea P.A., and Santagada V. Eur. J. Med. Chem 36 (2001) 873
24. Caliendo G., Fiorino F., Perissutti E., Severino B., Scolaro D., Gessi S., Cattabriga E., Borea P.A., and Santagada V. Eur. J. Med. Chem 16 (2002) 15
25. Fiorino F., Perissutti E., Severino B., Santagada V., Cirillo D., Terracciano S., Massarelli P., Bruni G., Collavoli E., Renner C., and Caliendo G. J. Med. Chem. 48 (2005) 5495
26. Fiorino F., Severino B., De Angelis F., Perissutti E., Frecentese F., Massarelli P., Bruni G., Collavoli E., Santagada V., and Caliendo G. Arch. Pharm. Chem. 341 (2008) 20
27. Fiorino F., Severino B., De Angelis F., Perissutti E., Magli E., Frecentese F., Esposito A., Massarelli P., Nencini C., Viti B., Santagada V., and Caliendo G. Die Pharm. 64 (2009) 555
28. Sauve G., Rao V.S., Lajoie G., and Belleau B. Can. J. Chem. 63 (1985) 3089
29. easyfit 1.4, 1989-1991, Matteo Vaccari and Mario Negri Institute, Milan, Italy.
30. Cheng Y.C., and Prusoff W.H. Biochem. Pharmacol. 2 (1973) 3099
31. Scatchard G. Ann. N.Y. Acad. Sci. 51 (1949) 660
32. Lopez-Rodriguez M.L., Morcillo M.J., Fernandez E., Benhamù B., Tejada I., Ayala D., Viso A., Campillo M., Pardo L., Delgado M., Manzanares J., and Fuentes J.A. J. Med. Chem. 48 (2005) 2548
33. Siracusa M.A., Salerno L., Modica M.N., Pittalà V., Romeo G., Amato M.E., Nowak M., Bojarski A.J., Mereghetti I., Cagnotto A., and Mennini T. J. Med. Chem. 51 (2008) 4529
34. Abou-Gharbia M.A., Childers Jr. W.E., Fletcher H., McGaughey G., Patel U., Webb M.B., Yardley J., Andree T., Boast C., Kucharik Jr. R.J., Marquis K., Morris H., Scerni R., and Moyer J.A. J. Med. Chem. 42 (1999) 5077
35. Morphy R., and Rankovic Z. J. Med. Chem. 48 (2005) 6523
36. Zlatović M.V., Šukalović V.V., Schneider C., and Roglić G.M. Bioorg. Med. Chem. 14 (2006) 2994
37. Schlegel J.R., and Peroutka S.J. Biochem. Pharmacol. 35 (1986) 1943
38. Herndon J.L., Ismaiel A., Ingher S.P., Teitler M., and Glennon R.A. J. Med. Chem. 35 (1992) 4903
39. Billard W., Ruperto V., Grosby G., Iorio L.C., and Barnett. Life Sci. 3 (1985) 1885
40. Creese I., Schneider R., and Snyder S.H. Eur. J. Pharmacol. 46 (1977) 377
41. Greengrass P., and Brenner R. Eur. J. Pharmacol. 55 (1979) 323
42. Perry B.D., and U' Prichar D.C. Eur. J. Pharmacol. 76 (1981) 461