Design, synthesis, and acetylcholinesterase inhibitory activity of novel coumarin analogues

Bioorganic and Medicinal Chemistry

Volumn 16, Issue 17, 2008, Pages 8011-8021

  Zhou, Xiang ^a   Wang, Xiao Bing ^a   Wang, Tao ^a   Kong, Ling Yi ^a  

^a CHINA PHARMACEUTICAL UNIVERSITY   (China)

Author keywords

Acetylcholinesterase inhibitor; Alzheimer's disease; Coumarin; Design; Synthesis

Indexed keywords

3 (4 BENZOYLPIPERAZINE 1 CARBONYL)COUMARIN; 3 (4 METHYLPIPERAZIN 1 CARBONYL)COUMARIN; 3 (4 PHENYLPIPERAZIN 1 CARBONYL)COUMARIN; 3 (MORPHOLINO 4 CARBONYL)COUMARIN; 3 [4 (2 METHOXYPHENYL)PIPERAZINE 1 CARBONYL]COUMARIN; 3 [4 (2 TOLYL)PIPERAZINE 1 CARBONYL]COUMARIN; 3 [4 (2,5 DICHLOROPHENYL)PIPERAZINE 1 CARBONYL]COUMARIN; 3 [4 (4 CHLOROPHENYL)PIPERAZINE 1 CARBONYL]COUMARIN; 3 [4 (4 METHOXYPHENYL)PIPERAZINE 1 CARBONYL]COUMARIN; 3 [4 (4 METHYLBENZOYL)PIPERAZINE 1 CARBONYL]COUMARIN; 3 [4 (4 METHYLPHENYL)PIPERAZINE 1 CARBONYL]COUMARIN; 4 [4 (2 TOLYL)PIPERAZIN 1 YL] 6 [[4 (2 TOLYL)PIPERAZIN 1 YL]METHYL]COUMARIN; 4 CHLORO 6 [(4 PHENYLPIPERAZIN 1 YL)METHYL]COUMARIN; 4 CHLORO 6 [[4 (2 METHOXYPHENYL)PIPERAZIN 1 YL]METHYL]COUMARIN; 4 CHLORO 6 [[4 (2 TOLYL)PIPERAZIN 1 YL]METHYL]COUMARIN; 4 CHLORO 6 [[4 (4 ETHOXYPHENYL)PIPERAZIN 1 YL]METHYL]COUMARIN; 4 CHLORO 6 [[4 (4 METHOXYPHENYL)PIPERAZIN 1 YL]METHYL]COUMARIN; 4 METHOXY 6 [(4 BENZOYLPIPERAZIN 1 YL)METHYL]COUMARIN; 4 METHOXY 6 [(4 PHENYLPIPERAZIN 1 YL)METHYL]COUMARIN; 4 METHOXY 6 [[4 (2 METHOXYPHENYL)PIPERAZIN 1 YL]METHYL]COUMARIN; 4 METHOXY 6 [[4 (2 METHYLPHENYL)PIPERAZIN 1 YL]METHYL]COUMARIN; 4 METHOXY 6 [[4 (4 CHLOROPHENYL)PIPERAZIN 1 YL]METHYL]COUMARIN; 4 METHOXY 6 [[4 (4 METHOXYBENZOYL)PIPERAZIN 1 YL]METHYL]COUMARIN; 4 METHOXY 6 [[4 (4 METHOXYPHENYL)PIPERAZIN 1 YL]METHYL]COUMARIN; 4 METHOXY 6 [[4 (4 TOLYL)PIPERAZIN 1 YL]METHYL]COUMARIN; ACETYLCHOLINESTERASE; COUMARIN DERIVATIVE; DONEPEZIL; UNCLASSIFIED DRUG; UNINDEXED DRUG;

ALZHEIMER DISEASE; ANIMAL TISSUE; ARTICLE; CONTROLLED STUDY; DRUG ACTIVITY; DRUG DESIGN; DRUG SYNTHESIS; ELECTROPHORUS; ENZYME INHIBITION; NONHUMAN; STRUCTURE ACTIVITY RELATION;

ACETYLCHOLINESTERASE; CHOLINESTERASE INHIBITORS; COUMARINS; DRUG DESIGN; DRUG EVALUATION, PRECLINICAL; ENZYME ACTIVATION; MOLECULAR STRUCTURE; STEREOISOMERISM; STRUCTURE-ACTIVITY RELATIONSHIP;

ELECTROPHORUS ELECTRICUS;

EID: 50249237889     PISSN: 09680896     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.bmc.2008.07.068     Document Type: Article

References (38)

1. Terry Jr. A.V., and Buccafusco J.J. J. Pharmacol. Exp. Ther. 306 (2003) 821
2. Selkoe D.J. Physiol. Rev. 81 (2001) 741
3. Wilkinson D.G., Francis P.T., Schwam E., and Payne-Parrish J. Drugs Aging 21 (2004) 453
4. Johannsen P. CNS Drugs 18 (2004) 757
5. Doraiswamy P.M. CNS Drugs 16 (2002) 811
6. Castro A., Conde S., Rodri{dotless}'guez-Franco M.I., and Marti{dotless}'nez A. Mini-Rev. Med. Chem 2 (2002) 37
7. Shvaloff A., Neuman E., and Guez D. Physchoparmacol. Bull. 32 (1996) 343
8. Wilcock G.K. Neurodegeneration 5 (1996) 505
9. Perry E.K. Br. Med. Bull. 42 (1986) 63
10. Bartus R.T., Dean L.D., Beer B., and Lippa A.S. Science 217 (1982) 408
11. Winkler J., Thal L., Gage F., and Fisher L.J. J. Mol. Med. 76 (1998) 555
12. Jhon V., Lieberburg I., and Thorsett E.D. Annu. Rep. Med. Chem. 28 (1993) 197
13. Moos W.H., and Hershenson F.M. DN&P 2 (1989) 397
14. Bullock R., and Dengiz A.. Int. J. Clin. Pract. 59 (2005) 817
15. De Ferrari G.V., Canales M.A., Shin I., Weiner L.M., Silman I., and Inestrosa N.C. Biochemistry 40 (2001) 10447
16. Inestrosa N.C., Alvarez A., Perez C.A., Moreno R.D., Vicente M., Linker C., Casanueva O.I., Soto C., and Garrido J. Neuron 16 (1996) 881
17. Hardy J., and Selkoe D.J. Science 297 (2002) 353
18. Giacobini E. Neurochem. Res. 28 (2003) 515
19. Castro A., and Marti{dotless}'nez A. Mini-Rev. Med. Chem. 1 (2001) 267
20. Bolognesi M.L., Andrisano V., Bartolini M., Banzi R., and Melchiorre C. J. Med. Chem. 48 (2005) 24
21. Zhang N., and Casida J.E. Bioorg. Med. Chem. 10 (2002) 1281
22. Weinstock M. CNS Drugs 12 (1999) 307
23. Sussman J.L., Harel M., Frolow F., Oefner C., Goldman A., Toker L., and Silman I. Science 253 (1991) 872
24. Harel M., Quinn D.M., Nair H.K., Silman I., and Sussman J.L. J. Am. Chem. Soc. 118 (1996) 2340
25. Radic Z., Pickering N.A., Vellom D.C., Camp S., and Taylor P. Biochemistry 32 (1993) 12074
26. Taylor P., Mayer R.T., and Himel C.M.. Mol. Pharmacol. 45 (1994) 74
27. Pang Y.-P., Quiram P., Jelacic T., Hong F., and Brimjoin S. J. Biol. Chem. 271 (1996) 23646
28. Quinn D.M. Chem. Rev. 87 (1987) 955
29. Hoerr R., and Noeldner M. CNS Drug Rev. 8 (2002) 143
30. Sugimoto H., Yamanishi Y., Iimura Y., and Kawakami Y. Curr. Med. Chem. 7 (2000) 303
31. Kryger G., Silman I., and Sussman J.L. J. Physiol. Paris 92 (1998) 191
32. Bartolucci C., Perola E., Pilger C., Fels G., and Lamba D. Proteins 42 (2001) 182
33. Dexeus F.H., Logothetis C.J., Sella A., Fitz K., Amato R., Reuben J.M., and Dozier N. J. Clin. Oncol. 8 (1990) 325
34. Lunney E.A., Hagen S.E., Domagala J.M., Humblet C., Kosinski J., Tait B.D., Warmus J.S., Wilson M., Ferguson D., Hupe D., Tummino P.J., Baldwin E.T., Bhat T.N., Liu B., and Ericksim J.W. J. Med. Chem. 37 (1994) 2664
35. Rampa A., Bisi A., Valenti P., Recanatini M., Cavalli A., Andrisano V., Cavrini V., Fin L., Buriani A., and Giusti P. J. Med. Chem. 41 (1998) 3976
36. Bruhlmann C., Ooms F., Carrupt P.A., Testa B., Catto M., Leonetti F., Altomare C., and Carotti A. J. Med. Chem. 44 (2001) 3195
37. Kontogiorgis C.A., and Hadjipavlou-Litina D.J. J. Med. Chem. 48 (2005) 6400
38. Ellman G.L., Courtney K.D., Andres B., and Feartherstone R.M. Biochem. Pharmacol. 7 (1961) 88