Synthesis, biological evaluation and modeling studies of dual binding AChE inhibitors

Medicinal Chemistry Research

Volumn 11, Issue 4, 2002, Pages 219-237

  Castro, Ana ^a   Hernandez, Laura ^a   Dorronsoro, Isabel ^a   Saenz, Patricia ^b   Pérez, Concepción ^a   Kalko, Susana ^c   Orozco, Modesto ^c   Luque, F Javier ^c   Martínez, Ana ^a  

^a INSTITUTO DE QUÍMICA MÉDICA   (Spain)

^b UNIVERSIDAD DE LA REPÚBLICA   (Uruguay)

^c UNIVERSITY OF BARCELONA   (Spain)

Author keywords

[No Author keywords available]

Indexed keywords

1 (4 METHOXYPHENACYL) 4 PHENYLIMIDAZOLE; 1 (4 METHOXYPHENYL) 4 PHENYLCARBAMOYLIMIDAZOLE; BENZYL 1 (4 METHOXYPHENYL)CARBAMOYL 4 IMIDAZODITHIOCARBOXYLATE; CHOLINESTERASE INHIBITOR; DONEPEZIL; IMIDAZOLE DERIVATIVE; METHYL 1 (4 METHOXYPHENYL)CARBAMOYL 4 IMIDAZODITHIOCARBOXYLATE; UNCLASSIFIED DRUG;

ALZHEIMER DISEASE; ARTICLE; CARBON NUCLEAR MAGNETIC RESONANCE; CHOLINESTERASE INHIBITION; DRUG BINDING SITE; DRUG POTENCY; DRUG STRUCTURE; DRUG SYNTHESIS; ENZYME INHIBITION; MOLECULAR DYNAMICS; NONHUMAN; PHARMACOPHORE; PROTON NUCLEAR MAGNETIC RESONANCE; TORPEDO CALIFORNICA;

EID: 0036441863     PISSN: 10542523     EISSN: None     Source Type: Journal    
DOI: None     Document Type: Article

References (31)

1. McDowell, I. Aging 2001, 13, 143-162.
2. Ventura, M.; Sternon, J. J. Pharm. Belg. 2001, 56, 62-68.
3. Sramek, J. J.; Veroff, A. E.; Cutler, N. R. Expert Opin. Investig. Drugs 2001, 10, 741-752.
4. Sussman, J. L.; Harel, M.; Frolow, F.; Oefner, C.; Goldman, A.; Toker, L.; Silman, I. Science 1991, 253, 872-879.
5. Barril, X.; Orozco, M.; Luque, F. J. Mini Rev. Med. Chem. 2001, 1, 255-266.
6. Saxena, A.; Redman, A. M.; Jiang, X.; Lockridge, O.; Doctor, B. P. Biochemistry 1997, 36, 14642-51.
7. Castro, A.; Martinez, A. Mini Rev. Med. Chem. 2001, 1, 267-272.
8. Muñoz, F.J.; Aldunate, R.; Inestrosa, N.C. Neuroreport. 1999, 10, 3621-3625.
9. Alvarez, A.; Opazo, C.; Alarcón, R.; Garrido, J.; Inestrosa, N. C. J. Mol. Biol. 1997, 272 348-361.
10. De Ferrari, G. V.; Canales, M. A.; Shin, I.; Weiner, L. M.; Silman, I.; Inestrosa, N. C. Biochemistry 2001, 40, 10447-10457.
11. Inestrosa, N. C.; Alarcón, R. J. Physiol. 1998, 92, 341-344.
12. Talesa, V. N. Mech. Ageing Dev. 2001, 122, 1961-1969.
13. Johnson, G.; Moore, S. W. Biochem. Biophys. Res. Comm. 1999, 258, 758-762.
14. Rampa, A.; Bisi, A.; Belluti, F.; Gobbi, S.; Valenti, P.; Andrisano, V.; Cavrini, C.; Cavalli, A.; Recanatini, M. Bioorg. Med Chem. 2000, 8, 497-506.
15. Borroni, B.; Colciaghi, F.; Pastorino, L.; Pettenati, C.; Cottini, E.; Rozzini, L.; Monastero, R.; Lenzi, G. L.; Cattabeni, F.; Di Luca, M.; Padovani, A. Arch. Neurol. 2001, 58, 442-446.
16. Castro, A.; Richards, W. G.; Lyne, P. D. Med. Chem. Res. 1999, 9, 98-107.
17. Lew, A.; Chamberlin, A. R. Bioorg. Med. Chem. Lett. 1999, 9, 3267-3272.
18. Martínez, A.; Lanot, C.; Perez, C.; Castro, A.; López-Serrano, P.; Conde, S. Bioorg. Med. Chem. 2000, 8, 731-738.
19. Martínez, A.; Fernadez, E.; Castro, A.; Conde, S.; Rodriguez-Franco, M. I.; Baños, J. E.; Badia, A. Eur. J. Med. Chem. 2000, 35, 913-922.
20. Ellman, G. L.; Courtney, K. D.; Andres, B.; Featherstone, R. M. Biochem. Pharmacol. 1961, 7, 88-95.
21. Grant, R.L.; Pyman, F.L. J. Chem. Soc. 1921, 119, 1899-1902.
22. Kryger, G.; Silman, I.; Sussman, J. L. Structure 1999, 7, 297-307.
23. Wlodek, S. T.; Antosiewicz, J.; McCammon, J. A.; Straatsma, T. P.; Gilson, M. K.; Briggs, J. M.; Humblet, C.; Sussman, J. L. Biopolymers 1996, 38, 109-117.
24. Gaussian 98. Rev. A.7. Frisch, M. J.; Trucks, G. W.; Schlegel, H. B.; Scuseria, G. E.; Robb, M. A.; Cheeseman, J. R.; Zakrzewski, V. G.; Montgomery, Jr., J. A.; Stratmann R. E.; Burant, J. C.; Dapprich, S.; Millam, J. M.; Daniels, A. D.; Kudin, K. N.; Strain, M. C.; Farkas, O.; Tomasi, J.; Barone, V.; Cossi, M.; Cammi, R.; Mennucci, B.; Pomelli, C.; Adamo, C.; Clifford, S.; Ochterski, J.; Petersson, G. A.; Ayala, P. Y.; Cui, Q.; Morokuma, K.; Malick, D. K.; Rabuck, A. D.; Raghavachari, K.; Foresman, J. B.; Cioslowski, J.; Ortiz, J. V.; Baboul, A. G.; Stefanov, B. B.; Liu, G.; Liashenko, A.; Piskorz, P.; Komaromi, I.; Gomperts, R.; Martin, R. L.; Fox, D. J.; Keith, T.; Al-Laham, M. A.; Peng, C. Y.; Nanayakkara, A.; Gonzalez, C.; Challacombe, M.; Gill, P. M. W. Johnson, B.; Chen, W.; Wong, M. W.; Andres, J. L.; Gonzalez, C.; Head-Gordon, M.; Replogle, E. S.; Pople, J. A. Gaussian, Inc., Pittsburgh PA, 1998.
25. Mestres, J.; Rohrer, D. C.; Maggiora, G. M. J. Comput. Chem. 1997, 18, 934-935.
26. Fradera, X.; Knegtel, R. M. A.; Mestres, J. Proteins 2000, 40, 623-636.
27. Jorgensen, W. L.; Chandrasekhar, J.; Madura, J. D.; Impey, R. W.; Klein, M. L. J. Chem. Phys. 1983, 79, 926-935.
28. Cornell, W. D.; Cieplak, P.; Bayly, C. I.; Gould, I. R.; Merz, K.; Ferguson, D. M.; Spellmeyer, D. C.; Fox, T.; Caldwell, J. W.; Kollman, P. A. J. Am. Chem. Soc. 1995, 117, 5179-5197.
29. Bayly, C. I.; Cieplak, P.; Cornell, W. D.; Kollman, P. A. J. Chem. Phys. 1993, 97, 10269-10280.
30. Ryckaert, J. P.; Ciccotti, G.; Berendsen, H. J. C. J. Comput. Phys. 1977, 23, 327-341.
31. Case, D. A.; Pearlman, D. A.; Caldwell, J. C.; Cheatham, T. E.; Ross, W. S.; Simmerling, C.; Darden, T.; Merz, K. M.; Stanton, R. V.; Cheng, A.; Vincent, J. J.; Crowley, M.; Ferguson, D. M.; Radmer, R.; Seibel, G. L.; Singh, U. C.; Weiner, P.; Kollman, P. A. AMBER5; University of Califomia: San Francisco, 1997.