Design, synthesis and preliminary pharmacological evaluation of rigid analogues of the nicotinic agonist 1,1-dimethyl-4-phenylpiperazinium iodide (DMPP)

Arkivoc

Volumn 2004, Issue 5, 2004, Pages 286-300

  Guandalini, Luca ^a   Martini, Elisabetta ^a   Gualtieri, Fulvio ^a   Romanelli, M Novella ^a   Varani, Katia ^b  

^a UNIVERSITY OF FLORENCE   (Italy)

^b UNIVERSITY OF FERRARA   (Italy)

Author keywords

Hexahydro pyrazino 1,2 a indoles; Nicotinic receptors ligands; Tetrahydropyrazino 1,2 a indoles; Tetrahydropyrido 4 ,3 :4,5 pyrrolo 1,2 a pyrazines

Indexed keywords

1 (3 PYRIDYL)PIPERAZINE DERIVATIVE; 1,1 DIMETHYL 4 PHENYLPIPERAZINIUM IODIDE; 2,2 DIMETHYL 1,2,3,4 TETRAHYDROPYRAZINO[1,2 A]INDOL 2 IUM IODIDE; CYTISINE; NICOTINIC AGENT; PIPERAZINE DERIVATIVE; UNCLASSIFIED DRUG;

ANIMAL TISSUE; ARTICLE; BINDING AFFINITY; BRAIN CORTEX; CONTROLLED STUDY; DRUG DESIGN; DRUG RECEPTOR BINDING; DRUG SCREENING; DRUG SYNTHESIS; NONHUMAN; PHARMACOPHORE; RAT;

EID: 2942648761     PISSN: 14246376     EISSN: None     Source Type: Journal    
DOI: None     Document Type: Article

References (33)

1. Millar, N. S. Biochem. Soc. Trans. 2003, 31 (Part 4), 869-74.
2. Hogg, R. C.; Raggenbass, M.; Bertrand, D. Rev. Physiol. Biochem. Pharmacol. 2003, 147, 1-46.
3. Steinlein, O. K.Curr. Drug Target CNS Neurol. Disord. 2002, 1, 443-8.
4. Rozycka, A.; Trzeciak, W. H. J. Appl. Genet. 2003, 44, 197-207.
5. Engel, A.; Ohno, K.; Sine, S. M. Muscle Nerve 2003, 27, 4-25.
6. Decker, M. W.; Meyer, M. D.; Sullivan, J. P. Expert Opin. Investig. Drugs 2001, 10, 1819-1830.
7. Unwin, N.; Toyoshima, C.; Kubalek, E. J. Cell. Biol. 1988, 107, 1123-1138.
8. Unwin, N. J. Struct. Biol. 1998, 121, 181-190.
9. Unwin, N. Nature 1995, 373, 37-43.
10. Miyazawa, A.; Fujiyoshi, Y.; Unwin, N. Nature 2003, 423, 949-955.
11. Brejc, K.; van Dijk, W. J.; Klaassen, R. V.; Schuurmans, M.; van der Oost, J.; Smit, A. B.; Sixma, T. K. Nature 2001, 411, 269-276.
12. Le Novère, N.; Grutter, T.; Changeux, J.-P. Proc. Natl. Acad. Sci. U.S.A. 2002, 99, 3210-3215.
13. Costa, V.; Nistri, A.; Cavalli, A.; Carloni, P. Br. J. Pharmacol. 2003, 140, 912-931.
14. Schapira, M.; Abagyan, R.; Totrov, M. BMC Struct. Biol. 2002, 2, 1-8.
15. Beers, W. H.; Reich, E. Nature 1970, 228, 917-922.
16. Glennon, R. A.; Herndon, J. L.; Dukat, M. Med.Chem. Res. 1994, 4, 461-473.
17. Nicolotti, O.; Pellegrini-Calace, M.; Carrieri, A.; Altomare, C.; Centeno, N. B.; Sanz, F.; Carotti, A. J. Comput-Aid. Mol. Des. 2001, 15, 859-872.
18. Tonder, J. E.; Olesen, P. H.; Hansen, J. B.; Begtrup, M.; Pettersson, I. J. Comput-Aid. Mol. Des. 2001, 15, 247-258.
19. Nicolotti, O.; Pellegrini-Calace, M.; Altomare, C.; Carotti, A.; Carrieri, A.; Sanz, F. Curr. Med. Chem. 2002, 9, 1-29.
20. Gohlke, H.; Schwarz, S.; Gündisch, D.; Tilotta, M. C.; Weber, A.; Wegge, T.; Seitz, G. J. Med. Chem. 2003, 46, 2031-2048.
21. Abreo, M. A.; Lin, N.-H.; Garvey, D. S.; Gunn, D. E.; Hettinger, A. M.; Wasicak, J. T.; Pavlik, P. A.; Martin, Y. C.; Donnelly-Roberts, D. L.; Anderson, D. J.; Sullivan, J. P.; Williams, M.; Arneric, S. P.; Holladay, M. W. J. Med. Chem. 1996, 39, 817-825.
22. Manetti, D.; Bartolini, A.; Borea, P. A.; Bellucci, C.; Dei, S.; Ghelardini, C.; Gualtieri, F.; Romanelli, M. N.; Scapecchi, S.; Teodori, E.; Varani, K. Bioorg. Med. Chem. 1999, 7, 457-465.
23. Romanelli, M. N.; Manetti, D.; Scapecchi, S.; Borea, P. A.; Dei, S.; Bartolini, A.; Ghelardini, C.; Gualtieri, F.; Guandalini, L.; Varani, K. J. Med. Chem. 2001, 44, 3946-3955.
24. Boksa, P.; Quirion, R. Eur. J. Pharmacol. 1987, 139, 323-333.
25. Dijkstra, G. D. H. Rec. Trav. Chim. Pays-Bas 1993, 112, 151-160.
26. Chothia, C.; Pauling, P. Acta Cryst. 1978, B34, 2986-2989.
27. Rajur, S. B.; Merwade, A. Y.; Hendi, S. B.; D., B. I. Indian J. Chem. 1989, 28B, 1065-1068.
28. Freed, M. E. U.S. 3317524, 1967; Chem. Abstr. 68:21956.
29. Hlasta, D. J.; Luttinger, D.; Perrone, M. H.; Silbernagel, M. J.; Ward, S. J.; Haubrich, D. R. J. Med. Chem. 1987, 30, 1555-1562.
30. Mokrosz, J. L.; Boksa, J.; Bojarski, A. J.; Charakchieva-Minol, S. Med. Chem. Res. 1993, 3, 240-248.
31. Fisher, M. H.; Matzuk, A. R.J. Heterocyclic Chem. 1969, 6, 775-6.
32. Lukas, R. J. In Diversity of interacting receptors. New York, 1995; Vol. 757.
33. Flores, C. M.; Rogers, S. W.; Pabreza, L. A.; Wolfe, B. B.; Kellar, K. J. Mol. Pharmacol. 1991, 41, 31-37.