Design, synthesis and structure-Activity relationships of dual inhibitors of acetylcholinesterase and serotonin transporter as potential agents for Alzheimer's disease

Bioorganic and Medicinal Chemistry

Volumn 11, Issue 9, 2003, Pages 1935-1955

  Toda, Narihiro ^a   Tago, Keiko ^a   Marumoto, Shinji ^a   Takami, Kazuko ^a   Ori, Mayuko ^a   Yamada, Naho ^a   Koyama, Kazuo ^a   Naruto, Shunji ^a   Abe, Kazumi ^a   Yamazaki, Reina ^a   Hara, Takao ^a   Aoyagi, Atsushi ^a   Abe, Yasuyuki ^a   Kaneko, Tsugio ^a   Kogen, Hiroshi ^a  

^a DAIICHI SANKYO CO   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

4 [1 METHYLAMINO 3 (4 NITROPHENOXY)PROPYL]PHENOL; ACETYLCHOLINESTERASE; DIMETHYLCARBAMIC ACID 3 [3 (4 METHOXYPHENOXY) 1 METHYLAMINOPROPYL]PHENYL ESTER; DIMETHYLCARBAMIC ACID 4 (1 METHYLAMINO 3 PHENOXYPROPYL)PHENYL ESTER; DIMETHYLCARBAMIC ACID 4 (1 METHYLAMINO 3,4 TOLYLOXYPROPYL)PHENYL ESTER; DIMETHYLCARBAMIC ACID 4 [1 DIMETHYLAMINO 3 (4 NITROPHENOXY)PROPYL]PHENYL ESTER; DIMETHYLCARBAMIC ACID 4 [1 ETHYLAMINO 3 (4 NITROPHENOXY)PROPYL]PHENYL ESTER; DIMETHYLCARBAMIC ACID 4 [1 METHYLAMINO 2 (4 NITROPHENOXY)ETHYL]PHENYL ESTER; DIMETHYLCARBAMIC ACID 4 [1 METHYLAMINO 3 (2 NITROPHENOXY)PROPYL]PHENYL ESTER; DIMETHYLCARBAMIC ACID 4 [1 METHYLAMINO 3 (3 NITROPHENOXY)PROPYL]PHENYL ESTER; DIMETHYLCARBAMIC ACID 4 [1 METHYLAMINO 3 (4 NITROPHENOXY)PROPYL]PHENYL ESTER; DIMETHYLCARBAMIC ACID 4 [1 METHYLAMINO 3 (4 TRIFLUOROMETHYLPHENOXY)PROPYL]PHENYL ESTER; DIMETHYLCARBAMIC ACID 4 [1 METHYLAMINO 4 (4 NITROPHENOXY)BUTYL]PHENYL ESTER; DIMETHYLCARBAMIC ACID 4 [3 (4 CHLOROPHENOXY) 1 METHYLAMINOPROPYL]PHENYL ESTER; DIMETHYLCARBAMIC ACID 4 [3 (4 CYANOPHENOXY) 1 METHYLAMINOPROPYL]PHENYL ESTER; DIMETHYLCARBAMIC ACID 4 [3 (4 FLUOROPHENOXY) 1 METHYLAMINOPROPYL]PHENYL ESTER; DIMETHYLCARBAMIC ACID 4 [3 (4 METHOXYPHENOXY) 1 METHYLAMINOPROPYL]PHENYL ESTER; DIMETHYLCARBAMIC ACID 4 [3 (4 NITROPHENOXY) 1 PIPERAZIN 1 YLPROPYL]PHENYL ESTER; DIMETHYLCARBAMIC ACID 4 [3 (4 NITROPHENOXY) 1 PYRROLIDIN 1 YLPROPYL]PHENYL ESTER; DIPEPTIDYL CARBOXYPEPTIDASE INHIBITOR; DONEPEZIL; ETHYLCARBAMIC ACID 4 [1 METHYLAMINO 3 (4 NITROPHENOXY)PROPYL]PHENYL ESTER; FLUOXETINE; METHYLCARBAMIC ACID 4 [1 METHYLAMINO 3 (4 NITROPHENOXY)PROPYL]PHENYL ESTER; N,N DIMETHYL 2 [4 [1 METHYLAMINO 3 (4 NITROPHENOXY)PROPYL]PHENYL]ACETAMIDE; RIVASTIGMINE; SEROTONIN TRANSPORTER; SEROTONIN UPTAKE INHIBITOR; UNCLASSIFIED DRUG; UNINDEXED DRUG; [1 (4 DIMETHYLCARBAMOYLOXYPHENYL) 3 (4 NITROPHENOXY)PROPYL]TRIMETHYLAMMONIUM IODIDE;

ALZHEIMER DISEASE; ANIMAL EXPERIMENT; ANIMAL TISSUE; ARTICLE; BRAIN; CONTROLLED STUDY; CRYSTAL STRUCTURE; DRUG DESIGN; DRUG POTENCY; DRUG SYNTHESIS; ENZYME INHIBITION; MOLECULAR MODEL; MOUSE; NONHUMAN; RAT; STRUCTURE ACTIVITY RELATION;

EID: 0037401391     PISSN: 09680896     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0968-0896(03)00091-9     Document Type: Article

References (26)

1. (a) Wurtman R.J. Sci. Am. 252:1985;48.
2. (b) Altman H.J. Alzheimer's Diseases Problems, Prospects and Perspectives. 1987;Plenum, New York.
3. (a) Enz A., Amstutz R., Boddeke H., Gmelin G., Malanowski J. Prog. Brain Res. 98:1993;431.
4. (b) Millard C.B., Broomfield C.A. J. Neurochem. 64:1995;1909.
5. Summers W.K., Majovski L.V., Marsh G.M., Tachiki K., Kling A. N. Engl. J. Med. 315:1983;1241.
6. Rogers S.L., Farlow M.R., Doody R.S., Mohs R., Friedhoff L.T. Neurology. 50:1998;136.
7. Forette F., Anand R., Gharabawi G. Eur. J. Neurol. 6:1999;423.
8. (a) Benzi G., Moretti A. Eur. J. Pharmacol. 346:1998;1.
9. (b) Giacobini E. Jpn, J, Pharmacol. 74:1997;225.
10. (a) Berger A.K., Fratiglioni L., Forsell Y., Winblad B., Backman L. Neurology. 53:1999;1998.
11. (b) Harwood D.G., Sultzer D.L., Wheatley M.V. Neuropsychiatry, Neuropsychol. Behav. Neurol. 13:2000;83.
12. Lyketsos C.G., Sheooard J.M., Steele C.D., Kopunek S., Steinberg M., Baker A.S., Brandt J., Rabins P.V. Am. J. Psychiatry. 157:2000;1686.
13. Golstein J., Schreiber S., Velkeniers B., Vanhaelst L. Eur. J. Pharmacol. 91:1983;239.
14. Dechant K.L., Clissold S.P. Drugs. 52:1991;625.
15. (a) Mackenna M.T., Proctor G.R., Young L.C., Harvey A.L. J. Med. Chem. 40:1997;3516.
16. (b) Hirai K., Kato K., Nakayama T., Hayako H., Ishihara Y., Goto G., Miyamoto M. J. Pharmocol. Exp. Ther. 280:1997;1261.
17. (a) Kryger G., Silman I., Sussman J.L. J. Physiol Paris. 92:1988;191.
18. (b) Sugimoto H. Chem. Rec. 1:2001;63.
19. Kaur J., Zhang M.-Q. Curr. Med. Chem. 7:2000;273.
20. Profft E., Becker F.-J. J. Prakt. Chem. 30:1965;18.
21. For a recent review, see: Farina V., Krishnamurthy V., Scott W.J. Org. React. 50:1997;1.
22. Jourdant A., Zamora E.G., Zhu J. J. Org. Chem. 67:2002;3163.
23. Kogen H., Toda N., Tago K., Marumoto S., Takami K., Ori M., Yamada N., Koyama K., Naruto S., Abe K., Yamazaki R., Hara T., Aoyagi A., Abe Y., Kaneko T. Org. Lett. 4:2002;3359.
24. 4=H) no longer displayed anti-SERT activity.
25. For (S)-6j, no reuptake of norepinephrine (>1000 nM) and dopamine (>1000 nM) was observed.
26. Ellman G.L., Courtney D., Andres V. Jr., Featherstone R.M. Biochem. Pharmacol. 7:1961;88.