7-Arylpiperazinylalkyl and 7-tetrahydroisoquinolinylalkyl derivatives of 8-alkoxy-purine-2,6-dione and some of their purine-2,6,8-trione analogs as 5-HT1A, 5-HT2A, and 5-HT7 serotonin receptor ligands

Bioorganic and Medicinal Chemistry

Volumn 15, Issue 15, 2007, Pages 5239-5250

  Chłoń Rzepa, Grazyna ^a   Zmudzki, Paweł ^a   Zajdel, Paweł ^a   Bojarski, Andrzej J ^b   Duszyńska, Beata ^b   Nikiforuk, Agnieszka ^b   Tatarczyńska, Ewa ^b   Pawłowski, Maciej ^a  

^a JAGIELLONIAN UNIVERSITY MEDICAL COLLEGE   (Poland)

^b INSTITUTE OF PHARMACOLOGY   (Poland)

Author keywords

5 HT1A; 5 HT2A; 5 HT7 receptor ligands; Long chain arylpiperazines; Purine 2,6,8 triones; Purine 2,6 diones

Indexed keywords

7 [3 (1,2,3,4 TETRAHYDROISOQUINOLIN 2 YL)PROPYL] 8 PROPOXY 1,3 DIMETHYL 3,7 DIHYDROPURINE 2,6 DIONE; 7 [3 (4 PHENYLPIPERAZIN 1 YL)PROPYL] 1,3 DIMETHYL 7,9 DIHYDRO 3H PURINE 2,6,8 TRIONE; 7 [3 (4 PHENYLPIPERAZIN 1 YL)PROPYL] 8 ETHOXY 1,3 DIMETHYL 3,7 DIHYDROPURINE 2,6 DIONE; 7 [3 (4 PHENYLPIPERAZIN 1 YL)PROPYL] 8 PROPOXY 1,3 DIMETHYL 3,7 DIHYDROPURINE 2,6 DIONE; 7 [3 [1,2,3,4 TETRAHYDROISOQUINOLIN 2 YL]PROPYL] 1,3 DIMETHYL 7,9 DIHYDRO 3H PURINE 2,6,8 TRIONE; 7 [3 [4 (2 METHOXYPHENYL)PIPERAZIN 1 YL]PROPYL] 8 ETHOXY 1,3 DIMETHYL 3,7 DIHYDROPURINE 2,6 DIONE; 7 [3 [4 (2 METHOXYPHENYL)PIPERAZIN 1 YL]PROPYL] 8 PROPOXY 1,3 DIMETHYL 3,7 DIHYDROPURINE 2,6 DIONE; 7 [3 [4 (3 CHLOROPHENYL)PIPERAZIN 1 YL]PROPYL] 1,3 DIMETHYL 7,9 DIHYDRO 3H PURINE 2,6,8 TRIONE; 7 [3 [4 (3 CHLOROPHENYL)PIPERAZIN 1 YL]PROPYL] 8 ETHOXY 1,3 DIMETHYL 3,7 DIHYDROPURINE 2,6 DIONE; 7 [3 [4 (3 CHLOROPHENYL)PIPERAZIN 1 YL]PROPYL] 8 PROPOXY 1,3 DIMETHYL 3,7 DIHYDROPURINE 2,6 DIONE; 7 [4 (1,2,3,4 TETRAHYDROISOQUINOLIN 2 YL)BUTYL] 8 ETHOXY 1,3 DIMETHYL 3,7 DIHYDROPURINE 2,6 DIONE; 7 [4 (1,2,3,4 TETRAHYDROISOQUINOLIN 2 YL)BUTYL] 8 PROPOXY 1,3 DIMETHYL 3,7 DIHYDROPURINE 2,6 DIONE; 7 [4 (1,2,3,4 TETRAHYDROISOQUINOLIN 2 YL)PROPYL] 8 ETHOXY 1,3 DIMETHYL 3,7 DIHYDROPURINE 2,6 DIONE; 7 [4 (4 PHENYLPIPERAZIN 1 YL)BUTYL] 1,3 DIMETHYL 7,9 DIHYDRO 3H PURINE 2,6,8 TRIONE; 7 [4 (4 PHENYLPIPERAZIN 1 YL)BUTYL] 8 ETHOXY 1,3 DIMETHYL 3,7 DIHYDROPURINE 2,6 DIONE; 7 [4 (4 PHENYLPIPERAZIN 1 YL)BUTYL] 8 PROPOXY 1,3 DIMETHYL 3,7 DIHYDROPURINE 2,6 DIONE; 7 [4 [4 (2 METHOXYPHENYL)PIPERAZIN 1 YL]BUTYL] 8 ETHOXY 1,3 DIMETHYL 3,7 DIHYDROPURINE 2,6 DIONE; 7 [4 [4 (2 METHOXYPHENYL)PIPERAZIN 1 YL]BUTYL] 8 PROPOXY 1,3 DIMETHYL 3,7 DIHYDROPURINE 2,6 DIONE; 7 [4 [4 (3 CHLOROPHENYL)PIPERAZIN 1 YL]BUTYL] 1,3 DIMETHYL 7,9 DIHYDRO 3H PURINE 2,6,8 TRIONE; 7 [4 [4 (3 CHLOROPHENYL)PIPERAZIN 1 YL]BUTYL] 1,3 DIMETHYL 8 PROPOXY 3,7 DIHYDROPURINE 2,6 DIONE; 7 [4 [4 (3 CHLOROPHENYL)PIPERAZIN 1 YL]BUTYL] 8 ETHOXY 1,3 DIMETHYL 3,7 DIHYDROPURINE 2,6 DIONE; ANTIDEPRESSANT AGENT; POSTSYNAPTIC RECEPTOR; PURINE DERIVATIVE; SEROTONIN 1A RECEPTOR; SEROTONIN 2A RECEPTOR; SEROTONIN 7 RECEPTOR; SEROTONIN AGONIST; UNCLASSIFIED DRUG; UNINDEXED DRUG; URIC ACID DERIVATIVE;

AGONIST; ANIMAL EXPERIMENT; ANIMAL TISSUE; ARTICLE; CONTROLLED STUDY; DRUG ACTIVITY; DRUG CLASSIFICATION; DRUG POTENCY; DRUG RECEPTOR BINDING; DRUG SCREENING; DRUG SYNTHESIS; HYPOTHERMIA; LOWER LIP; MALE; MOUSE; NONHUMAN; RAT; RECEPTOR AFFINITY; TRANQUILIZING ACTIVITY;

ANIMALS; BODY TEMPERATURE; DOSE-RESPONSE RELATIONSHIP, DRUG; LIGANDS; MALE; MICE; MOLECULAR STRUCTURE; MOTOR ACTIVITY; PURINES; RATS; RECEPTORS, SEROTONIN; SEROTONIN ANTAGONISTS; STRUCTURE-ACTIVITY RELATIONSHIP; SWIMMING;

MUS; RATTUS;

EID: 34249932365     PISSN: 09680896     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.bmc.2007.05.017     Document Type: Article

References (26)

1. Hedlund P.B., and Sutcliffe J.G. Trends Pharmacol. Sci. 25 (2004) 481
2. Leopoldo M. Curr. Med. Chem. 11 (2004) 629
3. Byrtus H., Pawłowski M., Charakchieva-Minol S., Duszyńska B., Mokrosz M.J., Mokrosz J.L., and Zejc A. Arch. Pharm. (Weinheim) 6 (1996) 283
4. Zajdel P., Subra G., Bojarski A.J., Duszyńska B., Pawłowski M., and Martinez J. Bioorg. Med. Chem. Lett. 16 (2006) 3406
5. Chojnacka-Wójcik E., Kłodzińska A., Drabczyńska A., Pawłowski M., Charakchieva-Minol S., Chłoń G., and Gorczyca M. Eur. J. Med. Chem. 30 (1995) 587
6. Pawłowski M., Katlabi J., Drabczyńska A., Duszyńska B., Charakchieva-Minol S., Dereń-Wesołek A., Tatarczyńska E., Chojnacka-Wójcik E., Mokrosz M.J., and Bojarski A.J. Eur. J. Med. Chem. 34 (1999) 167
7. Jurczyk S., Kołaczkowski M., Maryniak E., Zajdel P., Pawłowski M., Tararczyńska E., Kłodzińska A., Chojnacka-Wójcik E., Bojarski A.J., Charakchieva-Minol S., Duszyńska B., Nowak G., and Macia{ogonek}g D. J. Med. Chem. 47 (2004) 2659
8. Pawłowski M., Chłoń G., Obniska J., Zejc A., Charakchieva-Minol S., and Mokrosz M.J. Il Farmaco 55 (2000) 461
9. Chłoń G., Pawłowski M., Duszyńska B., Szaro A., Tatarczyńska E., Kłodzińska A., and Chojnacka-Wójcik E. Pol. J. Pharmacol. 53 (2001) 359
10. Zajdel P., Bojarski A., Byrtus H., Chłoń-Rzepa G., Obniska J., Chevallet P., Martinez J., and Pawłowski M. Biomed. Chromatogr. 17 (2003) 312
11. Rockitt S., Wartchow R., Dudeck H., Drabczyńska A., and Kieć-Kononowicz K. Z. Naturforsch., B. J. Chem. Sci. 56 3 (2001) 319
12. http://pdsp.med.unc.edu/pdsp.php.
13. Forbes I.T., Douglas S., Gribble A.D., Ife R.J., Lightfoot A.P., Garner A.E., Riley G.J., Jeffrey P., Stevens A.J., Tania T.O., and Thomas D.R. Bioorg. Med. Chem. Lett. 12 (2002) 3341
14. Raubo P., Beer M.S., Hunt P.A., Huscroft I.T., London C., Stanton J.A., and Kulagowski J.J. Bioorg. Med. Chem. Lett. 47 (2006) 5451
15. Goodwin G.M., De Souza R.J., and Green A.R. Neuropharmacology 24 (1985) 1187
16. Forster E.A., Cliffe I.A., Bill D.J., Dover G.M., Jones D., Reilly Y., and Fletcher A. Eur. J. Pharmacol. 281 (1995) 81
17. Berendsen H.H.G., Jenck F., and Broekkamp C.L.E. Pharmacol. Biochem. Behav. 33 (1989) 821
18. Berendsen H.H.G., Broekkamp C.L.E., and van Delft A.M.L. Behav. Neural. Biol. 55 (1991) 214
19. Aron C., Simon P., Larousse C., and Boissier J.R. Neuropharmacology 10 (1971) 459
20. Porsolt R.D., Bertin A., and Jalfre M. Arch. Int. Pharmacodyn. 229 (1977) 327
21. Vermeulen E.S., van Smeden M., Schmidt A.W., Sprouse J.S., Wikstrom H.V., and Grol C.J. J. Med. Chem. 47 (2004) 5451
22. Deakin J.F.W. J. Psychopharmacol. 7 (1993) 283
23. De Vry J. Psychopharmacology 121 (1995) 1
24. Schreiber R., and De Vry J. Prog. Neuropsychopharmacol. Biol. Psychiatry 17 (1993) 87
25. Eckstein M., Gorczyca M., and Zejc A. Acta Pharm. Yugoslav. 22 (1972) 133
26. Aquirre N., Ballaz S., Lasheras B., and Del Rio J. Eur. J. Pharmacol. 346 (1998) 181