Synthesis of new N-(4-pyridyl)-1-aminopyrazoles and their muscarinic and adrenergic properties

Archiv der Pharmazie

Volumn 333, Issue 5, 2000, Pages 118-122

  Rodríguez Franco, María Isabel ^a   Dorronsoro, Isabel ^a   Martínez, Ana ^a   Pérez, Concepción ^a   Badía, Albert ^b   Baños, Josep E ^b  

^a INSTITUTO DE QUÍMICA MÉDICA   (Spain)

^b UNIVERSITAT AUTÒNOMA DE BARCELONA   (Spain)

Author keywords

1 Aminopyrazoles; 4 aminopyridines; Adrenergic properties; Alzheimer's disease; Muscarinic properties

Indexed keywords

ACETYLCHOLINESTERASE; ALPHA 2 ADRENERGIC RECEPTOR; BESIPIRDINE; ION CHANNEL; MUSCARINIC RECEPTOR; N (4 PYRIDYL) 1 AMINOPYRAZOLE DERIVATIVE; NEUROTRANSMITTER RECEPTOR; PIRENZEPINE; PYRAZOLE DERIVATIVE; QUINUCLIDINYL BENZILATE; TACRINE; UNCLASSIFIED DRUG;

ANIMAL TISSUE; ARTICLE; BINDING COMPETITION; BRAIN MEMBRANE; CONTROLLED STUDY; DRUG RECEPTOR BINDING; DRUG STRUCTURE; DRUG SYNTHESIS; ENZYME INHIBITION; IC 50; IN VITRO STUDY; NONHUMAN; PRIORITY JOURNAL; RAT;

ACETYLCHOLINESTERASE; ADRENERGIC AGONISTS; ALZHEIMER DISEASE; ANIMALS; CENTRAL NERVOUS SYSTEM; ENZYME INHIBITORS; MAGNETIC RESONANCE SPECTROSCOPY; MOLECULAR STRUCTURE; MUSCARINIC AGONISTS; PROTEIN BINDING; PYRAZOLES; PYRIDINES; RATS; RECEPTOR, MUSCARINIC M1; RECEPTORS, ADRENERGIC; RECEPTORS, MUSCARINIC; SYNAPTIC TRANSMISSION;

EID: 0342858880     PISSN: 03656233     EISSN: None     Source Type: Journal    
DOI: 10.1002/(SICI)1521-4184(20005)333:5<118::AID-ARDP118>3.0.CO;2-Q     Document Type: Article

References (21)

1. P. J. Whitehouse, D. L. Price, R. G. Sruble, A. W. Clark, J. T. Coyle, M. R. DeLong, Science 1982, 215, 1237-1239.
2. R. T. Bartus, R. L. Dean, B. Beer, A. S. Lippa, Science 1982, 217, 408-417.
3. Alzheimer Disease: From Molecular Biology to Therapy (Eds.: R. Becker, E. Giacobini), Birkhäuser, Boston, 1997, pp. 521-526.
4. M. W. Decker, J. L McGaugh., Synapse 1991, 7, 151-168.
5. G.S. Zubenko, J. Mossy, U. Kopp, Arch. Neurology 1990, 47, 209-214.
6. S. Thesleff, Neuroscience 1980, 5, 1413-1419.
7. W. K. Summers, L. V. Majovski, G. Marsh, K. Tachiki, A. King, New Engl. J. Med. 1986, 315, 1241-1245.
8. J. T. Klein, L. Davis, G. E. Olsen, G. S. Wong, F. P. Huger, C. P. Smith, W. W. Petko, M. Cornfeldt, J. C. Wilker, R. D. Blitzer, E. Landau, V. Haroutunian, L. L. Martin, R. C. Effland, J. Med. Chem. 1996, 39, 570-581.
9. A. Martínez, D. Alonso, A. Castro, V. J. Arán, I. Cardelús, J. E. Baños, A. Badía, Arch. Pharm. Pharm. Med. Chem. 1999, 332, 191-194.
10. A. Martínez, C. Lanot, P. López-Serrano, A. Castro, S. Conde, Bioorg. Med. Chem. 2000, in press.
11. A. Martínez, E. Fernández, A. Castro, S. Conde, M. I. Rodríguez-Franco, J. E. Baños, Third International Symposium on the Medicinal Chemistry of Neurodegenerative Disease 1997, p. 8. Key Biscaine (Florida).
12. M. Fierros, S. Conde, A. Martínez, P. Navarro, M. I. Rodríguez-Franco, Tetrahedron 1995, 51, 2417-2426.
13. M.I. Rodríguez-Franco, M. Fierros, A. Martínez, P. Navarro, S. Conde, Bioorg. Med. Chem. 1997, 5, 363-367.
14. J. Elguero, In: Comprehensive Heterocyclic Chemistry (Ed.: K. T. Potts) Pergamon Press, Oxford, 1984. Vol. 5, pp. 167-303.
15. M. I. Rodríguez-Franco, J. Dorronsoro, A. Castro, A. Martínez, Tetrahedron 2000, 56, 1739-1743.
16. A. Schotte, P. F. M. Janssen, W. Gommeren, H. M. L. Luyten, P. Van Gompel, A. S. Lesage, Psychopharmacology 1996, 124, 57-73.
17. L. Iturrino, P. Navarro, M. I. Rodríguez-Franco, M. Contreras, J. A. Escario, A. Martínez, M. R. Pardo, Eur. J. Med. Chem. 1987, 22, 445-451.
18. J. Elguero, A. Martínez, S. P. Singh, D. Kumar, J. Heterocycl. Chem. 1991, 8, 647-649.
19. Compound 1a has been previously described, using another synthetic method: A. Ohsawa, T. Kaihoh, T. Itoh, M. Okada, C. Kawabata, K. Yamaguchi, H. Igeta, Chem. Pharm. Bull. 1988, 36, 3838-3848.
20. L. J. Street, R. Barker, T. Book, C. O. Kneen, A. M. MacLeod, K. J. Merchant, G. A. Showell, J. Saunders, R. H. Herbert, S. B. Freedman, E. A. Harley, J. Med. Chem. 1990, 33, 2690-2694.
21. G. L. Ellman, K. D. Courtney, B. Andres, R. M. Featherstone, Biochem. Pharmacol. 1961, 7, 88-95.