Synthesis and in vitro evaluation of 7-methoxy-N-(pent-4-enyl)-1,2,3,4- tetrahydroacridin- 9-amine-new tacrine derivate with cholinergic properties

Bioorganic and Medicinal Chemistry Letters

Volumn 21, Issue 21, 2011, Pages 6563-6566

  Korabecny, Jan ^a   Musilek, Kamil ^c   Zemek, Filip ^b   Horova, Anna ^b   Holas, Ondrej ^a   Nepovimova, Eugenie ^a   Opletalova, Veronika ^a   Hroudova, Jana ^d   Fisar, Zdenek ^d   Jung, Young Sik ^e   Kuca, Kamil ^b,f  

^a Charles University in Prague Faculty of Pharmacy   (Czech Republic)

^b UNIVERSITY OF DEFENCE   (Czech Republic)

^c UNIVERSITY OF HRADEC KRALOVE   (Czech Republic)

^d CHARLES UNIVERSITY   (Czech Republic)

^e Korea Research Institute of Chemical Technology   (South Korea)

^f UNIVERSITY OF DEFENCE   (Czech Republic)

Author keywords

7 Methoxytacrine; Alzheimer disease; Cholinesterase inhibitors; Cholinesterases; Molecular modelling

Indexed keywords

7 METHOXY N (PENT 4 ENYL) 1,2,3,4 TETRAHYDROACRIDIN 9 AMINE; 9 AMINO 7 METHOXY N (PENT 4 ENYL) 1,2,3,4 TETRAHYDROACRIDINE; 9,9 DI(PENTANE 1,5 DIYLDIIMINO)DI(7 METHOXY 1,2,3,4 TETRAHYDROACRIDINE); TACRINE; TACRINE DERIVATIVE; UNCLASSIFIED DRUG;

ALZHEIMER DISEASE; ARTICLE; CHOLINERGIC ACTIVITY; DRUG BINDING; DRUG ELIMINATION; DRUG SCREENING; DRUG SYNTHESIS; IN VITRO STUDY; MOLECULAR MODEL;

EID: 80054788675     PISSN: 0960894X     EISSN: 14643405     Source Type: Journal    
DOI: 10.1016/j.bmcl.2011.08.042     Document Type: Article

References (24)

1. Schoenberg, B. S.; Kokmen, E.; Okazaki, H. Ann. Neurol. 1987, 22, 724.
2. Small, S. A. Arch. Neurol. 2001, 58, 360.
3. Cacabelos, R. Methods Mol. Biol. 2008, 448, 213.
4. (a) Knapp, M. J.; Knopman, D. S.; Solomon, P. R.; Pendlebury, W. W.; Davis, C. S.; Gracon, S. I. J. Am. Med. Assoc. 1994, 271, 985;
5. (b) Farlow, M.; Gracon, S. I.; Hershey, L. A.; Lewis, K. W.; Sadowsky, C. H.; Dolan-Ureno, J. J. Am. Med. Assoc. 1992, 268, 2523.
6. Giacobini, E. In Cognitive Enhancing Drugs; Buccafusco, J. J., Ed.; Birkhäuser Verlag: Basel, Boston, Berlin, 2004; pp 11-36.
7. Shaw, F. H.; Bentley, G. A. Aust. J. Exp. Biol. Med. Sci. 1953, 31, 573.
8. Patocka, J.; Jun, D.; Kuca, K. Curr. Drug Metab. 2008, 9, 332.
9. Patocka, J. Sbornik Ved. Prac. VLVDU Hradec Kralove 1986, 102, 123.
10. Patocka, J.; Bielavsky, J.; Fusek, J. Homeostasis 1994, 35, 299.
11. Korabecny, J.; Holas, O.; Musilek, K.; Pohanka, M.; Opletalova, V.; Dohnal, V.; Kuca, K. Lett. Org. Chem. 2010, 7, 327.
12. Bielavsky, J. Collect. Czech Chem. Commun. 1977, 42, 2723.
13. Hamulakova, S.; Kristian, P.; Jun, D.; Kuca, K.; Imrich, J.; Danihel, I.; Bohm, S.; Klika, K. D. Heterocycles 2008, 76, 1219.
14. Korabecny, J.; Musilek, K.; Holas, O.; Binder, J.; Zemek, F.; Marek, J.; Pohanka, M.; Opletalova, V.; Dohnal, V.; Kuca, K. Bioorg. Med. Chem. Lett. 2010, 20, 6093.
15. Korabecny, J.; Musilek, K.; Holas, O.; Nepovimova, E.; Jun, D.; Zemek, F.; Opletalova, V.; Patocka, J.; Dohnal, V.; Nachon, F.; Hroudova, J.; Fisar, Z.; Kuca, K. Molecules 2010, 15, 8804.
16. Pang, Y.-P.; Hong, F.; Quiram, P.; Jelacic, T.; Brimijon, S. J. Chem. Soc., Perkin Trans. 1 1997, 171.
17. Tetko, I. V.; Tanchuk, V. Y. J. Chem. Inf. Comput. Sci. 2002, 42, 1136.
18. Trott, O.; Olson, A. J. J. Comput. Chem. 2009, 31, 455.
19. Kryger, G.; Harel, M.; Giles, K.; Toker, L.; Velan, B.; Lazar, A.; Kronman, C.; Barak, D.; Ariel, N.; Shafferman, A.; Silman, I.; Sussman, J. L. Acta Crystallogr., Sect. D 2000, 56, 1385.
20. Nicolet, Y.; Lockridge, O.; Masson, P.; Fontecilla-Camps, J. C.; Nachon, F. J. Biol. Chem. 2003, 278, 41141.
21. Morris, G. M.; Goodsell, D. S.; Halliday, R. S.; Huey, R.; Hart, W. E.; Belew, R. K.; Olson, A. J. J. Comput. Chem. 1998, 19, 1639.
22. Pettersen, E. F.; Goddard, T. D.; Huang, C. C.; Couch, G. S.; Greenblatt, D. M.; Meng, E. C.; Ferrin, T. E. J. Comput. Chem. 2004, 25, 1605.
23. DeLano, W. L. The PyMOL Molecular Graphics System (2002) on the World Wide Web http://www.pymol.org.
24. Pohanka, M.; Jun, D.; Kuca, K. Talanta 2008, 77, 451.