Design, synthesis and evaluation of novel heterodimers of donepezil and huperzine fragments as acetylcholinesterase inhibitors

Bioorganic and Medicinal Chemistry

Volumn 21, Issue 3, 2013, Pages 676-683

  Hu, Yueqing ^a   Zhang, Jun ^a   Chandrashankra, Oormila ^a   Ip, Fanny C F ^a   Ip, Nancy Y ^a  

^a HONG KONG UNIVERSITY OF SCIENCE AND TECHNOLOGY   (Hong Kong)

Author keywords

Acetylcholinesterase; Alzheimer's disease; Heterodimer; Huperzine A

Indexed keywords

2 (3 CHLOROPROPYL) 5,6 DIMETHOXY 1 OXO INDAN 2 CARBOXYLIC ACID ETHYL ESTER; 2 (4 CHLOROBUTYL) 5,6 DIMETHOXY 1 OXO INDAN 2 CARBOXYLIC ACID ETHYL ESTER; 2 (5 BROMOPENTYL) 5,6 DIMETHOXY 1 OXO INDAN 2 CARBOXYLIC ACID ETHYL ESTER; 2 (6 BROMOHEXYL) 5,6 DIMETHOXY 1 OXO INDAN 2 CARBOXYLIC ACID ETHYL ESTER; 2 (7 BROMOHEPTYL) 5,6 DIMETHOXY 1 OXO INDAN 2 CARBOXYLIC ACID ETHYL ESTER; 2 (9 BROMONONYL) 5,6 DIMETHOXY 1 OXO INDAN 2 CARBOXYLIC ACID ETHYL ESTER; 2 [3 [2 BENZYLOXY 5,6,7,8 TETRAHYDROQUINOLIN 5 YLAMINO] PROPYL] 5,6 DIMETHOXYINDAN 1 ONE; 2 [4 [2 BENZYLOXY 5,6,7,8 TETRAHYDROQUINOLIN 5 YLAMINO] BUTYL] 5,6 DIMETHOXYINDAN 1 ONE; 2 [5 [2 BENZYLOXY 5,6,7,8 TETRAHYDROQUINOLIN 5 YLAMINO] PENTYL] 5,6 DIMETHOXYINDAN 1 ONE; 2 [6 [2 BENZYLOXY 5,6,7,8 TETRAHYDROQUINOLIN 5 YLAMINO] HEXYL] 5,6 DIMETHOXYINDAN 1 ONE; 2 [7 [2 BENZYLOXY 5,6,7,8 TETRAHYDROQUINOLIN 5 YLAMINO] HEPTYL] 5,6 DIMETHOXYINDAN 1 ONE; 2 [9 [2 BENZYLOXY 5,6,7,8 TETRAHYDROQUINOLIN 5 YLAMINO] NONYL] 5,6 DIMETHOXYINDAN 1 ONE; 5 [3 [5,6 DIMETHOXY 1 OXO INDAN 2 YL] PROPYLAMINO] 5,6,7,8 TETRAHYDRO 1H QUINOLIN 2 ONE; 5 [4 [5,6 DIMETHOXY 1 OXO INDAN 2 YL] BUTYLAMINO] 5,6,7,8 TETRAHYDRO 1H QUINOLIN 2 ONE; 5 [5 [5,6 DIMETHOXY 1 OXO INDAN 2 YL] PENTYLAMINO] 5,6,7,8 TETRAHYDRO 1H QUINOLIN 2 ONE; 5 [6 [5,6 DIMETHOXY 1 OXO INDAN 2 YL] HEXYLAMINO] 5,6,7,8 TETRAHYDRO 1H QUINOLIN 2 ONE; 5 [7 [5,6 DIMETHOXY 1 OXO INDAN 2 YL] HEPTYLAMINO] 5,6,7,8 TETRAHYDRO 1H QUINOLIN 2 ONE; 5 [9 [5,6 DIMETHOXY 1 OXO INDAN 2 YL] NONYLAMINO] 5,6,7,8 TETRAHYDRO 1H QUINOLIN 2 ONE; 5,6 DIMETHOXY 1 OXO INDAN 2 CARBOXYLIC ACID ETHYL ESTER; ACETYLCHOLINESTERASE; CARBENE; CHOLINESTERASE; CHOLINESTERASE INHIBITOR; CYCLOBUTANE; DONEPEZIL; HETERODIMER; HUPERZINE A; UNCLASSIFIED DRUG;

ARTICLE; DIASTEREOISOMER; DIMERIZATION; DRUG BINDING SITE; DRUG DESIGN; DRUG IDENTIFICATION; DRUG POTENCY; DRUG PROTEIN BINDING; DRUG SCREENING; DRUG STRUCTURE; DRUG SYNTHESIS; ENZYME ACTIVE SITE; ENZYME INHIBITION; IC 50; NONHUMAN; STRUCTURE ANALYSIS; TORPEDO CALIFORNICA;

ACETYLCHOLINESTERASE; ALKALOIDS; ANIMALS; CHOLINESTERASE INHIBITORS; DIMERIZATION; DOSE-RESPONSE RELATIONSHIP, DRUG; DRUG DESIGN; INDANS; MOLECULAR STRUCTURE; PIPERIDINES; RATS; RATS, SPRAGUE-DAWLEY; SESQUITERPENES; STRUCTURE-ACTIVITY RELATIONSHIP;

EID: 84872361274     PISSN: 09680896     EISSN: 14643391     Source Type: Journal    
DOI: 10.1016/j.bmc.2012.11.044     Document Type: Article

References (26)

1. J.L. Cummings, and S. Askin-Edgar CNS Drugs 13 2000 385
2. N.L. Batsch, and M.S. Mittelman World Alzheimer Report 2012 5
3. R.T. Bartus, R.L. Dean, B. Beer, and A.S. Lippa Science 217 1982 408
4. W. Thies, and L. Bleiler Alzheimers Dement. 8 2012 131
5. D. Munoz-Torrero, and P. Camps Curr. Med. Chem. 13 2006 399
6. Y.-P. Pang, P. Quiram, T. Jelacic, F. Hong, and S. Brimijoin J. Biol. Chem. 271 1996 23646
7. P.R. Carlier, D.M. Du, Y.F. Han, J. Liu, E. Perola, I.D. Williams, and Y.P. Pang Angew. Chem., Int. Ed. 39 2000 1775
8. P.R. Carlier, D.-M. Du, Y. Han, J. Liu, and Y.-P. Pang Bioorg. Med. Chem. Lett. 9 1999 2335
9. D. Alonso, I. Dorronsoro, L. Rubio, P. Muñoz, E. García-Palomero, M. Del Monte, A. Bidon-Chanal, M. Orozco, F.J. Luque, A. Castro, M. Medina, and A. Martínez Bioorg. Med. Chem. 13 2005 6588
10. D. Shao, C. Zou, C. Luo, X. Tang, and Y. Li Bioorg. Med. Chem. Lett. 14 2004 4639
11. P. Camps, X. Formosa, C. Galdeano, T. Gomez, D. Munoz-Torrero, M. Scarpellini, E. Viayna, A. Badia, M.V. Clos, A. Camins, M. Pallas, M. Bartolini, F. Mancini, V. Andrisano, J. Estelrich, M. Lizondo, A. Bidon-Chanal, and F.J. Luque J. Med. Chem. 51 2008 3588
12. I. Bolea, J. Juarez-Jimenez, C. Rios, M. Chioua, R. Pouplana, F.J. Luque, M. Unzeta, J. Marco-Contelles, and A. Samadi J. Med. Chem. 54 2011 825
13. V. Tumiatti, A. Minarini, M.L. Bolognesi, A. Milelli, M. Rosini, and C. Melchiorre Curr. Med. Chem. 2010 1825 17
14. E. Viayna, T. Gomez, C. Galdeano, L. Ramirez, M. Ratia, A. Badia, M.V. Clos, E. Verdaguer, F. Junyent, A. Camins, M. Pallas, M. Bartolini, F. Mancini, V. Andrisano, M.P. Arce, M.I. Rodríguez-Franco, A. Bidon-Chanal, F.J. Luque, P. Camps, and D. Munoz-Torrero ChemMedChem 2010 1855 5
15. M. Monte-Millan, E. Garcia-Palomero, R. Valenzuela, P. Usan, C. de Austria, P. Munoz-Ruiz, L. Rubio, I. Dorronsoro, A. Martinez, and M. Medina J. Mol. Neurosci. 30 2006 85
16. G. Koellner, G. Kryger, C.B. Millard, I. Silman, J.L. Sussman, and T. Steiner J. Mol. Biol. 296 2000 713
17. A. Saxena, J.M. Fedorko, C.R. Vinayaka, R. Medhekar, Z. Radić, P. Taylor, O. Lockridge, and B.P. Doctor Eur. J. Biochem. 270 2003 4447
18. G. Kryger, I. Silman, and J.L. Sussman Structure 7 1999 297
19. M.L. Raves, M. Harel, Y.P. Pang, I. Silman, A.P. Kozikowski, and J.L. Sussman Nat. Struct. Biol. 4 1997 57
20. D.M. Wong, H.M. Greenblatt, H. Dvir, P.R. Carlier, Y.-F. Han, Y.-P. Pang, I. Silman, and J.L. Sussman J. Am. Chem. Soc. 125 2003 363
21. Y. Kawakami, A. Inoue, T. Kawai, M. Wakita, H. Sugimoto, and A.J. Hopfinger Bioorg. Med. Chem. 4 1996 1429
22. J.V. Greenhill J. Chem. Soc. C 1971 2699
23. G.R. Pettit, W.C. Fleming, and K.D. Paull J. Org. Chem. 33 1968 1089
24. G.L. Ellman, K.D. Courtney, V. Andres Jr., and R.M. Featherstone Biochem. Pharmacol. 7 1961 88
25. H. Sugimoto, Y. Yamanishi, Y. Iimura, and Y. Kawakami Curr. Med. Chem. 7 2000 303
26. M.G. Cardozo, Y. Iimura, H. Sugimoto, Y. Yamanishi, and A.J. Hopfinger J. Med. Chem. 35 1992 584