Synthesis and AChE inhibitory activity of new chiral tetrahydroacridine analogues from terpenic cyclanones

European Journal of Medicinal Chemistry

Volumn 45, Issue 2, 2010, Pages 526-535

  Santos Pisoni, Diego dos ^a   Sobieski da Costa, Jessé ^a   Gamba, Douglas ^a   Petzhold, Cesar Liberato ^a   César de Amorim Borges, Antonio ^a   Ceschi, Marco Antonio ^a   Lunardi, Paula ^a   Saraiva Gonçalves, Carlos Alberto ^a  

^a FEDERAL UNIVERSITY OF RIO GRANDE DO SUL   (Brazil)

Author keywords

AChE inhibitory activity; Acridines; Tacrine

Indexed keywords

(1,2,4) 9 AMINO 2,4 METHANO 1,3,3 TRIMETHYL 1,2,3,4 TETRAHYDROACRIDINE; (1,4) 9 AMINO 1,4 DIISOPROPYL 1,2,3,4 TETRAHYDROACRIDINE; (1,4) 9 AMINO 4 TERT BUTYL 1 METHYL 1,2,3,4 TETRAHYDROACRIDINE; (2) 9 AMINO 2 ISOPROPYL 2,3 DIHYDRO 1H CYCLOPENTA[B]QUINOLINE; (2) 9 AMINO 2 METHYL 2,3 DIHYDRO 1H CYCLOPENTA[B]QUINOLINE; (2,4) 9 AMINO 2,4 METHANO 3,3 DIMETHYL 1,2,3,4 TETRAHYDROACRIDINE; (3) 9 AMINO 3 ISOPROPYL 1,2,3,4 TETRAHYDROACRIDINE; (3) 9 AMINO 3 METHYL 1,2,3,4 TETRAHYDROACRIDINE; (9) 11 AMINO 6,6,9 TRIMETHYL 9,10 DIHYDRO 6H CYCLOHEPTA[B]QUINOLIN 7(8H) ONE; 9 AMINOTETRAHYDROACRIDINE DERIVATIVE; ANTHRANILIC ACID; CHOLINESTERASE INHIBITOR; KETONE DERIVATIVE; TACRINE DERIVATIVE; TERPENE; UNCLASSIFIED DRUG;

ANIMAL EXPERIMENT; ARTICLE; CATALYST; CHEMICAL MODIFICATION; CHIRALITY; CHOLINESTERASE INHIBITION; CYCLODEHYDRATION; DRUG SYNTHESIS; ENANTIOSELECTIVITY; MALE; NONHUMAN; QUANTITATIVE STRUCTURE ACTIVITY RELATION; RAT;

ACETYLCHOLINESTERASE; ACRIDINES; ANIMALS; BORANES; CATALYSIS; CHOLINESTERASE INHIBITORS; MALE; NITRILES; RATS; RATS, WISTAR; STEREOISOMERISM; TERPENES;

EID: 73849108496     PISSN: 02235234     EISSN: 17683254     Source Type: Journal    
DOI: 10.1016/j.ejmech.2009.10.039     Document Type: Article

References (56)

1. Bartus R.T., Dean R.L., Beer B., and Lippa A.S. Science 217 (1982) 408-417
2. Leifer B.P. J. Am. Geriatr. Soc. 51 (2003) 281-288
3. Marco-Contelles J., León R., López M.G., García A.G., and Villarroya M. Eur. J. Med. Chem. 41 (2006) 1464-1469
4. Alonso D., Dorronsoro I., Rubio L., Muñoz P., García-Palomero E., Del Monte M., Bidon-Chanal A., Orozco M., Luque F.J., Castro A., Medina M., and Martínez A. Bioorg. Med. Chem. 13 (2005) 6588-6597
5. Cacabelos R., Alvarez A., Lombardi V., Fernández-Novoa L., Corzo L., Pérez P., laredo M., Pichel V., Hernández A., Varela M., Figueroa J., Prous Jr. J., Windisch M., and Vigo C. Drugs Today 36 (2000) 415-499
6. Francis P.T., Palmer A.M., Snape M., and Wilcock G.K. J. Neurol. Neurosurg. Psychiatr 66 (1999) 137-147
7. Tang H., Wei Y.-B., Zhang C., Ning F.-X., Qiao W., Huang S.-L., Ma L., Huang Z.-S., and Gu L.-Q. Eur. J. Med. Chem. 44 (2009) 2523-2532
8. Castro A., and Martinez A. Mini-Rev. Med. Chem. 1 (2001) 267-272
9. Taylor P. Neurology 51 (1998) S30-S35
10. Viegas Jr. C., Bolzani V.d.S., Barreiro E.J., and Fraga C.A.M. Mini-Rev. Med. Chem. 5 (2005) 915-926
11. Rodríguez-Franco M.I., Fernández-Bachiller M.I., Pérez C., Hernández-Ledesma B., and Bartolomé B. J. Med. Chem. 49 (2006) 459-462
12. Francotte P., Graindorge E., Boverie S., de Tullio P., and Pirotte B. Curr. Med. Chem. 11 (2004) 1757-1778
13. Watkins P.B., Zimmerman H.J., Knapp M.J., Gracon S.I., and Lewis K.W. J. Am. Med. Assoc. 271 (1994) 992-998
14. Ames D.J., Bhathal P.S., Davies B.M., Fraser J.R.E., Gibson P.R., and Roberts S. Aust. N.Z.J. Med. 20 (1990) 193-195
15. + currents at a cholinergic nerve terminal. Current Research in Alzheimer Therapy, E. Giacobini, R. Becker, Eds. Taylor and Francis: New York, (1988) pp 191-197.
16. McKenna M.T., Proctor G.R., Young L.C., and Harvey A.L. J. Med. Chem. 40 (1997) 3516-3523
17. Drukarch B., Leysen J.E., and Stoof J.C. Life Sci. 42 (1988) 1011-1017
18. Jossan S.S., Adem A., Winblad B., and Oreland L. Pharmacol. Toxicol. 71 (1992) 213-215
19. Kaul P.N. J. Pharm. Pharmacol. 14 (1962) 243-248
20. Antuono P.G. Arch. Intern. Med. 155 (1995) 1766-1772
21. Shutske G.M., Pierrat F.A., Kapples K.J., Cornfeldt M.L., Szewczak M.R., Huger F.P., Bores G.M., Haroutunian V., and Davis K.L. J. Med. Chem. 32 (1989) 1805-1813
22. Gregor V.E., Emmerling M.R., Lee C., and Moore C.J. Bioorg. Med. Chem. Lett. 2 (1992) 861-864
23. Recanatini M., Cavalli A., Belluti F., Piazzi L., Rampa A., Bisi A., Gobbi S., Valenti P., Andrisano V., Bartolini M., and Cavrini V. J. Med. Chem. 43 (2000) 2007-2018
24. Liu J.S., Zhu Y.L., Yu C.M., Zhou Y.Z., Han Y.Y., Wu F.W., and Qi B.F. Can. J. Chem. 64 (1986) 837-839
25. Jiang H., Luo X., and Bai D. Curr. Med. Chem. 10 (2003) 2231-2252
26. Zhang H.Y., Yan H., and Tang X.C. Cell. Mol. Neurobiol. 28 (2008) 173-183
27. Camps P., Formosa X., Muñoz-Torrero D., Petrignet J., Badia A., and Clos M.V. J. Med. Chem. 48 (2005) 1701-1704
28. Camps P., Gómez E., Muñoz-Torrero D., Font-Bardia M., and Solans X. Tetrahedron 59 (2003) 4143-4151
29. Camps P., Contreras J., Font-Bardia M., Morral J., Muñoz-Torrero D., and Solans X. Tetrahedron: Asymmetry 9 (1998) 835-849
30. Camps P., El Achab R., Görbig D.M., Morral J., Muñoz-Torrero D., Badia A., Baños J.E., Vivas N.M., Barril X., Orozco M., and Luque F.J. J. Med. Chem. 42 (1999) 3227-3242
31. Camps P., Cusack B., Mallender W.D., El Achab R., Morral J., Muñoz-Torrero D., and Rosenberry T.L. Mol. Pharmacol. 57 (2000) 409-417
32. Camps P., El Achab R., Morral J., Muñoz-Torrero D., Badia A., Baños J.E., Vivas N.M., Barril X., Orozco M., and Luque F.J. J. Med. Chem. 43 (2000) 4657-4666
33. Frideling A., Faure R., Galy J.-P., Kenz A., Alkorta I., and Elguero J. Eur. J. Med. Chem. 39 (2004) 37-48
34. Proctor G.R., and Harvey A.L. Curr. Med. Chem. 7 (2000) 295-302
35. Gamba D., Pisoni D.S., da Costa J.S., Petzhold C.L., Borges A.C.A., and Ceschi M.A. J. Braz. Chem. Soc. 19 (2008) 1270-1276
36. Pisoni D.S., Gamba D., Fonseca C.V., da Costa J.S., Petzhold C.L., de Oliveira E.R., and Ceschi M.A. J. Braz. Chem. Soc. 2 (2006) 321-327
37. Djerassi C., and Krakower G.W. J. Am. Chem. Soc. 81 (1959) 237-242
38. Webster F.X., Rivas-Enterrios J., and Silverstein R.M. J. Org. Chem. 52 (1987) 689-691
39. Renz M., and Corma A. Eur. J. Org. Chem. (2004) 2036-2039
40. Elings J.A., Lempers H.E.B., and Sheldon R.A. Eur. J. Org. Chem. (2000) 1905-1911
41. Whitesell J.K., Lawrence R.M., and Chen H.-H. J. Org. Chem. 51 (1986) 4779-4784
42. Buschmann H., and Scharf H.-D. Synthesis 10 (1988) 827-830
43. Marshall J.A., Bartley G.S., and Wallace E.M. J. Org. Chem. 61 (1996) 5729-5735
44. Dalcanale E., and Montanari F. J. Org. Chem. 51 (1986) 567-569
45. Queiroga C.L., Ferracini V.L., and Marsaioli A.J. Phytochemistry 42 (1996) 1097-1103
46. Chang W.-S., Shia K.-S., Liu H.-J., and Ly T.W. Org. Biomol. Chem. 4 (2006) 3751-3753
47. M.L.A. von Holleben, M. Zucolotto, C.A. Zini, E.R. de Oliveira, 50 (1994) 973-978.
48. Moore J.A., and Kornreich L.D. Tetrahedron Lett. 20 (1963) 1277-1281
49. Marco-Contelles J., León R., De los Ríos C., García A.G., López M.G., and Villarroya M. Bioorg. Med. Chem. 14 (2006) 8176-8185
50. Girgis N.S., and Pedersen E.B. Synthesis (1985) 547-548
51. Ellman G.L., Courtney K.D., Andres V., and Featherstone R.M. Biochem. Pharmacol. 7 (1961) 88-95
52. Racchi M., Mazzucchelli M., Porrello E., Lanni C., and Govoni S. Pharmacol. Res. 50 (2004) 441-451
53. Li W.M., Kan K.K., Carlier P.R., Pang Y.P., and Han Y.F. Curr. Alzheimer Res. 4 (2007) 386-396
54. Paquette L.A., Maynard G.D., Ra C.S., and Hoppe M. J. Org. Chem. 54 (1989) 1408-1418
55. Barnhart R.W., Wang X., Noheda P., Bergens S.H., Whelan J., and Bosnich B. J. Am. Chem. Soc. 116 (1994) 1821-1830
56. Peterson G.L. A simplification of the protein assay method of Lowry et.al. which is more generally applicable. Anal. Biochem. 83 (1977) 346-356