From the selective serotonin transporter inhibitor citalopram to the selective norepinephrine transporter inhibitor talopram: Synthesis and structure-activity relationship studies

Journal of Medicinal Chemistry

Volumn 51, Issue 10, 2008, Pages 3045-3048

  Eildal, Jonas N N ^a,b   Andersen, Jacob ^a,b   Kristensen, Anders S ^a   Jørgensen, Anne Marie ^b   Bang Andersen, Benny ^b   Jørgensen, Morten ^b   Strømgaard, Kristian ^a  

^a UNIVERSITY OF COPENHAGEN   (Denmark)

^b H LUNDBECK A S   (Denmark)

Author keywords

[No Author keywords available]

Indexed keywords

[3 [1 (4 FLUOROPHENYL) 3,3 DIMETHYL 1,3 DIHYDROISOBENZOFURAN 1 YL]PROPYL]DIMETHYLAMINE; CITALOPRAM; NORADRENALIN TRANSPORTER; PROTEIN INHIBITOR; SEROTONIN TRANSPORTER; TALOPRAM;

ARTICLE; BIOLOGICAL ACTIVITY; DRUG POTENCY; DRUG SELECTIVITY; DRUG STRUCTURE; DRUG SYNTHESIS; INHIBITION KINETICS; STRUCTURE ACTIVITY RELATION;

ANIMALS; BENZOFURANS; BLOOD PLATELETS; BRAIN; CELL LINE; CITALOPRAM; HUMANS; NOREPINEPHRINE PLASMA MEMBRANE TRANSPORT PROTEINS; PROPYLAMINES; RATS; RECOMBINANT PROTEINS; SEROTONIN PLASMA MEMBRANE TRANSPORT PROTEINS; SEROTONIN UPTAKE INHIBITORS; STRUCTURE-ACTIVITY RELATIONSHIP; SYNAPTOSOMES;

EID: 43949130429     PISSN: 00222623     EISSN: None     Source Type: Journal    
DOI: 10.1021/jm701602g     Document Type: Article

References (24)

1. Gether, U.; Andersen, P. H.; Larsson, O. M.; Schousboe, A. Neurotransmitter transporters: molecular function of important drug targets. Trends Pharmacol. Sci. 2006, 27, 375-383.
2. Inoue, T.; Kusumi, I.; Yoshioka, M. Serotonin transporters. Curr. Drug Targets: CNS Neurol. Disord. 2002, 1, 519-529.
3. Waitekus, A. B.; Kirkpatrick, P. Duloxetine hydrochloride. Nat. Rev. Drug Discovery 2004, 3, 907-908.
4. Wong, D. T.; Perry, K. W.; Bymaster, F. P. Case history: the discovery of fluoxetine hydrochloride (Prozac). Nat. Rev. Drug Discov. 2005, 4, 764-774.
5. Zambrowicz, B. P.; Sands, A. T. Knockouts model the 100 best-selling drugs - Will they model the next 100. Nat. Rev. Drug Discovery 2003, 2, 38-51.
6. Petersen, P. V.; Lassen, N.; Hansen, V.; Huld, T.; Hjortkjær, J.; Holmblad, J.; Nielsen, I. M.; Nymark, M.; Pedersen, V.; Jørgensen, A.; Hougs, W. Pharmacological studies of a new series of bicyclic thymoleptics. Acta Pharmacol. Toxicol. 1966, 24, 121-133.
7. Petersen, P. V.; Lassen, N.; Nørgaard, J.; Huld, T. Antidepressant basic derivatives of phthalanes, iso-chromanes and iso-chromenes. U.S. Patent 3467675, 1969.
8. Bigler, A. J.; Bøgesø, K. P.; Toft, A.; Hansen, V. Quantitative structure-activity-relationships in a series of selective 5-HT uptake inhibitors. Eur. J. Med. Chem. 1977, 12, 289-295.
9. Hyttel, J.; Bøgesø, K. P.; Perregaard, J.; Sanchez, C. The pharmacological effect of citalopram resides in the (S)-(+)-enantiomer. J. Neural Transm. 1992, 88, 157-160.
10. Murdoch, D.; Keam, S. J. Escitalopram - A review of its use in the management of major depressive disorder. Drugs 2005, 65, 2379-2404.
11. Sanchez, C.; Bøgesø, K. P.; Ebert, B.; Reines, E. H.; Bræstrup, C. Escitalopram versus citalopram: the surprising role of the R-enantiomer. Psychopharmacology 2004, 174, 163-176.
12. Baumann, P.; Zullino, D. F.; Eap, C. B. Enantiomers' potential in psychopharmacology - a critical analysis with special emphasis on the antidepressant escitalopram. Eur. Neuropsychopharmacol. 2002, 12, 433-444.
13. Hyttel, J. Pharmacological characterization of selective serotonin reuptake inhibitors (SSRIs). Int. Clin. Psychopharmacol. 1994, 9, 19-26.
14. Bøgesø, K. P.; Christensen, A. V.; Hyttel, J.; Liljefors, T. 3-Phenyl-1-indanamines - potential antidepressant activity and potent inhibition of dopamine, norepinephrine, and serotonin uptake. J. Med. Chem. 1985, 28, 1817-1828.
15. Beak, P.; Musick, T. J.; Liu, C.; Cooper, T.; Gallagher, D. J. Selectivities in reaction of organolithium reagents with aryl bromides which bear proton-donating groups. J. Org. Chem. 1993, 58, 7330-7335.
16. Jeong, I.-Y.; Shio, M.; Nagao, Y. Palladium-catalyzed ring expansion of hydroxy methoxyallenylphthalans as a novel synthetic method for highly substituted 4-isochromanone derivatives. Heterocycles 2000, 52, 85-90.
17. Ellis, G. P.; Romney-Alexander, T. M. Cyanation of aromatic halides. Chem. Rev. 1987, 87, 779-794.
18. Zanon, J.; Klapars, A.; Buchwald, S. L. Copper-catalyzed domino halide exchange-cyanation of aryl bromides. J. Am. Chem. Soc. 2003, 125, 2890-2891.
19. Arvela, R. K.; Leadbeater, N. E. Rapid, easy cyanation of aryl bromides and chlorides using nickel salts in conjunction with microwave promotion. J. Org. Chem. 2003, 68, 9122-9125.
20. Bois, F.; Baldwin, R. M.; Kula, N. S.; Baldessarini, R. J.; Innis, R. B.; Tamagnan, G. Synthesis and monoamine transporter affinity of 3′-analogs of 2-beta-carbomethoxy-3-beta-(4′-iodophenyl)tropane (beta-CIT). Bioorg. Med. Chem. Lett. 2004, 14, 2117-2120.
21. Mortensen, O. V.; Kristensen, A. S.; Wiborg, O. Species-scanning mutagenesis of the serotonin transporter reveals residues essential in selective, high-affinity recognition of antidepressants. J. Neurochem. 2001, 79, 237-247.
22. Kristensen, A. S.; Larsen, M. B.; Johnsen, L. B.; Wiborg, O. Mutational scanning of the human serotonin transporter reveals fast translocating serotonin transporter mutants. Eur. J. Neurosci. 2004, 19, 1513-1523.
23. Bøgesø, K. P.; Toft, A. S. Anti-depressive substituted 1-dimethylaminopropyl-1-phenyl-phthalans. U.S. Patent 4,136,193, Jan. 23, 1979.
24. Petersen, P. V.; Lassen, N.; Ammitzbøll, T.; Nielsen, I. M.; Nymark, M.; Pedersen, V.; Franck, K. F. Further pharmacological studies of bicyclic thymoleptics. Acta Pharmacol. Toxicol. 1970, 28, 241-248.