Design of new cognition enhancers: From computer prediction to synthesis and biological evaluation

Journal of Medicinal Chemistry

Volumn 47, Issue 11, 2004, Pages 2870-2876

  Geronikaki, Athina A ^a   Dearden, John C ^b   Filimonov, Dmitrii ^c   Galaeva, Irina ^d   Garibova, Taissia L ^d   Gloriozova, Tatiana ^c   Krajneva, Valentina ^d   Lagunin, Alexey ^c   Macaev, Fliur Z ^e   Molodavkin, Guenadij ^d   Poroikov, Vladimir V ^c   Pogrebnoi, Serghei I ^e   Shepeli, Felix ^e   Voronina, Tatiana A ^d   Tsitlakidou, Maria ^a   Vlad, Liudmila ^e  

^a ARISTOTLE UNIVERSITY OF THESSALONIKI   (Greece)

^b LIVERPOOL JOHN MOORES UNIVERSITY   (United Kingdom)

^c INSTITUTE OF BIOMEDICAL CHEMISTRY   (Russian Federation)

^d INSTITUTE OF PHARMACOLOGY   (Russian Federation)

^e INSTITUTE OF CHEMISTRY   (Moldova)

Author keywords

[No Author keywords available]

Indexed keywords

(3 CHLOROBENZYLIDENE)THIAZOL 2 YLAMINE; (3 NITROBENZYLIDENE)THIAZOL 2 YLAMINE; (4 METHYLTHIAZOL 2 YL)(4 NITROBENZYLIDENE)AMINE; (4 NITROBENZYLIDENE)(4 PHENYLTHIAZOL 2 YL)AMINE; 4 (1,3 THIAZOL) 2 YLIMINOMETHYL)PHENOL; 4 (BENZOTHIAZOL 2 YLIMINOMETHYL)PHENOL; AMPHOLYTE; BENZOTHIAZOLE DERIVATIVE; DIAZEPINE DERIVATIVE; HETEROCYCLIC COMPOUND; IMIDAZOLE DERIVATIVE; INDOLE DERIVATIVE; INDOLIZINE DERIVATIVE; N (4 PHENYL 1,3 THIAZOL 2 YL)PHENYLMETHANIMINE; NOOTROPIC AGENT; OXAZOLE DERIVATIVE; PURINE DERIVATIVE; PYRIDINE DERIVATIVE; PYRIMIDINE DERIVATIVE; PYRROLE DERIVATIVE; SCOPOLAMINE; THIAZOLE DERIVATIVE; THIOPHENE DERIVATIVE; UNCLASSIFIED DRUG;

AMNESIA; ARTICLE; CARCINOGENICITY; COMPUTER PREDICTION; CONCENTRATION RESPONSE; DRUG ACTIVITY; DRUG DESIGN; DRUG EFFECT; DRUG MECHANISM; DRUG STRUCTURE; DRUG SYNTHESIS; MUTAGENICITY; PASSIVE AVOIDANCE; TOXICOLOGICAL PARAMETERS;

AMNESIA; ANIMALS; AVOIDANCE LEARNING; COMPUTER SIMULATION; DRUG DESIGN; MALE; NOOTROPIC AGENTS; OXAZOLES; RATS; SCOPOLAMINE; THIAZOLES;

EID: 2442652804     PISSN: 00222623     EISSN: None     Source Type: Journal    
DOI: 10.1021/jm031086k     Document Type: Article

References (32)

1. Cacabelos, R.; Alvarez, A.; Lombardi, V.; Fernandez-Novoa, L.; Corzo, L. ; Perez, P.; Laredo, M.; Pichel, V.; Hernandez, A.; Varela, M.; Figueroa, J.; Prous, J., Jr.; Windisch, M.; Vigo, C. Pharmacological treatment of Alzheimer disease: From psychotropic drugs and cholinesterase inhibitors to pharmacogenomics. Drugs Today 2000, 35 (7), 415-495.
2. Castro, A.; Conde, S.; Rodriguez-Franco, I.; Martinez, A. Non-cholinergic pharmacotherapy approaches to the future treatment of Alzheimer's disease. Mini Rev. Med. Chem. 2002, 2, 37-50.
3. Voronina, T. A. In Alzheimer disease: theraputic strategies; Birkhauser: Boston, 1994; pp 265-269.
4. Farcas, E.; De Wilde, M. C.; Kiliaan, A. J.; Luiten, P. G. M. Chronic Cerebral Hypoperfusion-Related Neuropathologic Changes and Compromised Cognitive Status: Window of Treatment. Drugs Today 2002, 38 (5), 365-376.
5. Gouliaev, A. H. and Senning, A. Piracetam and other structurally related nootropics. Brain Res. Rev. 1994, 19, 180-222.
6. Nicolov, R.; Dicova, M.; Nicolova, L.; Voronina, T.; Nerobkova, L.; Garibova, T. Methods Find. Exp. Clin. Pharmacol. 1987, 9 (8), 479-484.
7. Voronina T. A. Sov Med. Rev. G. Neuropharmacology 1992, 2, 51-106.
8. Poroikov, V. V.; Filimonov, D. A.; Borodina, Yu. V.; Lagunin, A. A.; Kos, A. Robustness of biological activity spectra predicting by computer program pass for noncongeneric sets of chemical compounds. J. Chem. Inf Comput. Sci. 2000, 40 (6), 1349-1355.
9. Web site: http//www.ibmh.msk.su/PASS.
10. Poroikov, V. V.; Filimonov, D. A.; Ihlenfeld, W.-D., Gloriozova, T. A.; Lagunin, A. A.; Borodina, Yu. V.; Stepanchikova, A. V. and Nicklaus, M. C. PASS Biological Activity Spectrum Predictions in the Enhanced Open NCI Database Browser. J. Chem. Inf. Comput. Sci. 2003, 43, 228-236.
11. Stepanchikova A. V., Lagunin A. A., Filimonov D. A., Poroikov V. V. Prediction of biological activity spectra for substances: evaluation on the diverse set of drug-like structures. Curr. Med. Chem. 2003, 10, 225-233.
12. Poroikov V. V., Filimonov D. A. How to acquire new biological activities in old compounds by computer prediction. J. Comput. Aid. Mol. Des. 2003, 16 (11), 819-824.
13. Dearden, J. C.; Barratt, M. D.; Benigni, R.; Bristol, D. W.; Combes, R. D.; Cronin, M. T. D.; Judson, P. N.; Payne, M. P.; Richard, A. M.; Tichy, M.; Worth, A. P. and Yourick, J. J. The development and validation of expert systems for predicting toxicity. ATLA 1997, 25, 223-252.
14. Gundertofte, K.; Jorgensen, F. S. Molecular Modelling and Prediction of Bioactivity; Kluwer Academic/Plenum Publishers: Norwell, MA, 2000.
15. Srivastava, P. N.; Rai, S. K. Some derivatives of 2-aminothiazole as potent local anaesthetic. Eur. J. Med. Chem. Chim. Ther. 1980, 15, 274.
16. Bhargava, P. N.; Nair, M. G. R. Synthesis of new local anaesthetics. J. Indian Chem. Soc. 1957, 34, 42-44.
17. Srivastava, P. K. and Srivastava, P. N. Synthesis of some local anesthetics, J. Med. Chem. 1970, 13, 304-305.
18. Lakhan, R., and Rai, B. J. Local Anaesthetics. IV. Synthesis and activity of 2-(N-substituted or N,N-disubstituted aminoacetamido)-4- or 4,5-disubstituted thiazoles. Il Farmaco, Ed. Sci. 1986, 41, 788.
19. Geronikaki, A.; Theophilidis, G. Synthesis of 2-(aminoacetylamino)thiazole derivatives and comparison of their local anaesthetic activity by the method of action potential. Eur. J. Med. Chem. 1992, 27, 709-716.
20. Vicini, P.; Amoretti, L.; Chiavarini, M.; Impicciatore, M. Synthesis and local anesthetic activity of alkylaminoacyl derivatives of 3-amino-1,2-benzisothiazoles. Il Farmaco 1990, 45, 933-944.
21. Klose, N.; Niedbolla, K.; Schwartz, K.; Bottcher, I. 4,5-Bis-(4-methoxyphenyl)-2-aryl-thio-azole mit antiphlogisher wirkung. Arch. Pharm. 1983, 316, 941-951.
22. Satsangi, R. K.; Zaidi, S. M.; Misra, V. C. 1-(4-Substituted -thiazol-2-yl) hydantoins as antiinflammatory and CNS active agents. Pharmazie 1983, 38, 341-342.
23. Pignatello, R.; Mazzone, S.; Panico, A. M.; Mazzone, G.; Penissi, G.; Castano, R.; Matera, M.; Blandino, G. Synthesis and biological evaluation of thiazolo-triazole derivatives. Eur. J. Med. Chem. 1991, 26, 929-938.
24. Hadjipavlou-Litina, D.; Geronikaki, A.; Sotiropoulou, E. Anti-inflammatory activity of aminoketones derivatives of 2,4-disubstituted thiazoles. Res. Commun. Chem. Pathol Pharmacol. 1993, 79, 355-362.
25. Raciti, G.; Mazzone, P.; Raudino, A.; Mazzone, G., and Cambria, A. Inhibition of rat liver mitochondrial monoamine oxidase by hydrazine-thiazole derivatives: structure-activity relationships. Bioorg. Med. Chem. 1995, 3 (11), 1485-1491.
26. Li, Q.; Woods, K. W.; Claiborne, A.; Gwaltney, S. L., II; Barr, K. J.; Liu, G.; Gehrke, L.; Credo, R. B.; Hui, Y. H.; Lee, J.; Warner, R. B.; Kovar, P.; Nukkala, M. A.; Zielinski, N. A.; Tahir, S. K.; Fitzgerald, M.; Kim, K. H.; Marsh, K.; Frost, D.; Ng, S. C.; Rosenberg, S.; Sham, H. L. Synthesis and Biological Evaluation of 2-Indolyloxazolines as a New Class of Tubulin Polymerization Inhibitors. Discovery of A-289099 as an Orally Active Antitumor Agent. Bioorg. Med. Chem. Lett. 2002, 12, 465-469.
27. Cooper, C. S.; Klock, P. L.; Chu, D. T. W.; Fernandes, P. B. The Synthesis and Antibacterial Activities of Quinolones Containing Five- and Six-Membered Heterocyclic Substituents at the 7-Position. J. Med. Chem. 1990, 33, 1246-1252.
28. Diana, G. D.; Otto, M. J.; Treasurywala, A. M.; McKinlay, M. A.; Oglesby, R. C.; Maliski, E. G.; Rossmann, M. G.; Smith, T. J. Enantiomeric Effects of Homologues of Disoxaril on the Inhibitory Activity against Human Rhinovirus-14. J. Med. Chem. 1988, 31, 540-544.
29. Cumin, R.; Bandels, R. F.; Haefely, W. E. Effects of the novel compound aniracetam (Ro 13-5057) upon impaired learning and memory in rodents. Psychopharmacology 1982, 78 (2), 104-111.
30. Web-site: http://www.mdli.com
31. Filimonov, D.; Poroikov, V.; Borodina, Yu.; Gloriozova, T. Chemical Similarity Assessment Through Multilevel Neighborhoods of Atoms: Definition and Comparison with the Other Descriptors. J. Chem. Inf. Comput. Sci. 1999, 39 (4), 666-670.
32. Ader, R.; Weijnen, A. W. M.; Moleman, P. Retention of a passive avoidance response as a function of the intensity. Psychon. Sci. 1972, 26 (3), 125-128.