Biologically active 1-arylpiperazines. Synthesis of new N-(4-aryl-1-piperazinyl)alkyl derivatives of quinazolidin-4(3H)-one, 2,3-dihydrophthalazine-1,4-dione and 1,2-dihydropyridazine-3,6-dione as potential serotonin receptor ligands

Molecules

Volumn 6, Issue 9, 2001, Pages 784-795

  Kowalski, Piotr ^a   Kowalska, Teresa ^a   Mokrosz, Maria J ^b   Bojarski, Andrzej J ^b   Charakchieva Minol, Sijka ^b  

^a CRACOW UNIVERSITY OF TECHNOLOGY   (Poland)

^b INSTITUTE OF PHARMACOLOGY   (Poland)

Author keywords

Arylpiperazines; Lactams; Serotonin receptor ligands

Indexed keywords

2 [3 (4 PHENYL 1 PIPERAZINYL)PROPYL] 1 PHENYL 1,2 DIHYDROPYRIDAZINE 3,6 DIONE; 2 [4 (4 PHENYL 1 PIPERAZINYL)BUTYL] 1 PHENYL 1,2 DIHYDROPYRIDAZINE 3,6 DIONE; 2 [4 [4 (2 PYRIMIDINYL) 1 PIPERAZINYL]BUTYL] 1 PHENYL 1,2 DIHYDROPYRIDAZINE 3,6 DIONE; 2,3 DIHYDRO 1,4 PHTHALAZINEDIONE; 3 [3 (4 PHENYL 1 PIPERAZINYL)PROPYL] 2 PHENYL 2,3 DIHYDROPHTHALAZINE 1,4 DIONE; 3 [3 (4 PHENYL 1 PIPERAZINYL)PROPYL]QUINAZOLIN 4(3H) ONE; 3 [3 [4 (2 PYRIMIDINYL) 1 PIPERAZINYL]PROPYL] 2 PHENYL 2,3 DIHYDROPHTHALAZINE 1,4 DIONE; 3 [3 [4 (2 PYRIMIDINYL) 1 PIPERAZINYL]PROPYL]QUINAZOLIN 4(3H) ONE; 3 [4 (4 PHENYL 1 PIPERAZINYL)BUTYL] 2 PHENYL 2,3 DIHYDROPHTHALAZINE 1,4 DIONE; 3 [4 (4 PHENYL 1 PIPERAZINYL)BUTYL]QUINAZOLIN 4(3H) ONE; 3 [4 [4 (2 PYRIMIDINYL) 1 PIPERAZINYL]BUTYL]QUINAZOLIN 4(3H) ONE; 3 [4 [4 (2 PYRIMIDYL) 1 PIPERAZINYL]BUTYL] 2 PHENYL 2,3 DIHYDROPHTHALAZINE 1,4 DIONE; MALEIC HYDRAZIDE; PHTHALAZINE DERIVATIVE; PIPERAZINE DERIVATIVE; QUINAZOLINE DERIVATIVE; SEROTONIN RECEPTOR; UNCLASSIFIED DRUG;

ARTICLE; DRUG ACTIVITY; DRUG STRUCTURE; DRUG SYNTHESIS;

EID: 0013004642     PISSN: 14203049     EISSN: None     Source Type: Journal    
DOI: 10.3390/60900784     Document Type: Article

References (30)

1. Hibert, M.F.; Gittos, M.W.; Middlemiss, D.N.; Mir, A.K.; Fozard, J.R. J. Med. Chem. 1988, 31, 1087.
2. Mellin, C.; Vallgarda, J.; Nelson, D.L.; Bjork, L.; Yu, H.; Anden, N.E.; Csoregh, I.; Arvidsson, L.E.; Hacksell, U. J. Med. Chem. 1991, 34, 497.
3. Chidester, C.G.; Lin, C.H.; Lahti, R.A.; Haadsma-Svensson, S.R.; Smith, M.W. J. Med. Chem. 1993, 36, 1301.
4. Agarwal, A.; Pearson, P.P.; Taylor, E.W.; Li, H.B.; Dahlgren, T.; Herslof, M.; Yang, Y.; Lambert, G.; Nelson, D.L.; Regan, J.W. J. Med. Chem. 1993, 36, 4006.
5. van Steen, B.J.; van Wijngaarden, I.; Tulp, M.T.; Soudijn, W. J. Med. Chem. 1994, 37, 2761.
6. Glennon, R.A.; Dukat, M. Serotonin ID research alert 1997, 2, 351.
7. Mokrosz, M.J.; Duszynska, B.; Bojarski, A.J.; Mokrosz, J.L. Bioorg. Med. Chem. 1995, 3, 533.
8. . Chilmonczyk, Z.; Szelejewska-Wozniakowska, A.; Cybulski, J.; Cybulski, M.; Koziol, A.E.; Gdaniec, M. Arch. Pharm. (Weinheim). 1997, 330, 146.
9. . Gaillard, P.; Carrupt, P.A.; Testa, B.; Schambel, P. J. Med. Chem. 1996, 39, 126.
10. 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-Wójcik, E. Arch. Pharm. (Weinheim) 1999, 332, 373.
11. a) Niementowski, S. J. Prakt. Chem. 1895, 51, 566;
12. b) Ried, W.; Stephan, W. Chem. Ber. 1962, 95, 3042.
13. a) Chattaway, F.D.; Tesh, W. J. Chem. Soc. 1920, 117, 711;
14. b) Axelrad, G.; Lamontanaro, D.M. J. Heterocyclic Chem. 1972, 9, 1407;
15. c) Baloniak, S.; Mroczkiewicz, A.; Kartusiak, A. Pol. J. Chem. 1996, 70, 1274.
16. a) Curtius, T; Foersterling, M.A. J. Prakt. Chem. 1895, 51, 371;
17. b) Chattaway, F.D.; Parkes, D.W. J. Chem. Soc. 1922, 121, 711;
18. c) Druey, J.; Hüni, A.; Meier, K.; Ringier, B.H.; Staehelin, A. Helv. Chim. Acta 1954, 37, 510;
19. d) Feuer, H.; White, E.H.; Wyman, J.E. J. Am. Chem. Soc., 1958, 80, 3790.
20. Axelrad, J.; Lamontanaro, D.M. J. Hetrocyclic Chem. 1972, 9, 1407.
21. Pring, B.G.; Swahn, K-G. Acta Chem. Scand. 1973, 27, 1891.
22. Kornet, M.J.; Varia, T.; Beaven, W. J. Heterocyclic Chem. 1983, 20, 1553.
23. Kornet, M.J. Eur. J. Med. Chem. 1986, 21, 529.
24. Zielinski, W.; Mazik, M. Pol. J. Chem. 1994, 68, 489.
25. Kowalska, T.; Kowalski, P.; Rutkowski, K.; Wozniak, M.; Kleinrok, Z.; Jagiello-Wojtowicz, E.; Szurska, G.; Chodkowska, A. Acta Pol. Pharmaceutica - Drug Res. 1994, 51, 143.
26. Mokrosz, M.J.; Kowalski, P.; Kowalska, T.; Majka, Z.; Duszynska, B.; Charakchieva-Minol, S.; Szaro, A.; Tatarczynska, E.; Klodzinska, A.; Chojnacka-Wojcik, E. Pol. J. Pharmacol. 1998, 50, 333.
27. Kowalski, P.; Mokrosz, M.J.; Majka, Z.; Kowalska, T.; Duszynska, B. J. Heterocyclic Chem. 2000, 37, 187.
28. Czuba, W.; Rutkowski, K.; Kowalski, P. Org. Mass Spectrom. 1978, 13, 203.
29. Porter, Q.N. Mass Spectrometry of Heterocyclic Compounds, Second Edition, John Wiley & Sons: New York - Chichester - Brisbane - Toronto - Singapore, 1985.
30. Bojarski, A.J.; Cegla, M.T.; Charakchieva-Minol, S.; Mokrosz, M.J.; Mackowiak, M.; Misztal, S.; Mokrosz, J.L. Pharmazie, 1993, 48, 289.