Synthesis and evaluation of a set of para-substituted 4-phenylpiperidines and 4-phenylpiperazines as monoamine oxidase (MAO) inhibitors

Journal of Medicinal Chemistry

Volumn 55, Issue 7, 2012, Pages 3242-3249

  Pettersson, Fredrik ^a   Svensson, Peder ^a   Waters, Susanna ^a   Waters, Nicholas ^a   Sonesson, Clas ^a  

^a NeuroSearch Sweden AB   (Sweden)

Author keywords

[No Author keywords available]

Indexed keywords

1 (4 METHOXYPHENYL) 4 PROPYLPIPERAZINE; 1 PHENYL 4 PROPYLPIPERAZINE; 1 PHENYLPIPERAZINE DERIVATIVE; 1 PROPYL 4 [4 (TRIFLUOROMETHYL)PHENYL]PIPERIDINE; 3 O METHYLDOPAMINE; 3,4 DIHYDROXYPHENYLACETIC ACID; 4 (4 CHLOROPHENYL) 1 PROPYLPIPERIDINE; 4 (4 METHOXYPHENYL) 1 PROPYLPIPERIDINE; 4 PHENYL 1 PROPYLPIPERIDINE; 4 PHENYLPIPERIDINE DERIVATIVE; AMINE OXIDASE (FLAVIN CONTAINING) ISOENZYME A; AMINE OXIDASE (FLAVIN CONTAINING) ISOENZYME B; MOCLOBEMIDE; MONOAMINE OXIDASE INHIBITOR; SELEGILINE; UNCLASSIFIED DRUG;

ANIMAL CELL; ANIMAL EXPERIMENT; ANIMAL TISSUE; ARTICLE; BINDING AFFINITY; BRAIN CORTEX; CONTROLLED STUDY; CORPUS STRIATUM; DIPOLE; DRUG BINDING; DRUG MEGADOSE; DRUG SYNTHESIS; ENZYME BINDING; HYDROPHOBICITY; IN VITRO STUDY; IN VIVO STUDY; LOW DRUG DOSE; NEUROCHEMISTRY; NONHUMAN; POLARIZATION; RAT; STRUCTURE ACTIVITY RELATION; SUBSTITUTION REACTION;

3,4-DIHYDROXYPHENYLACETIC ACID; ANIMALS; BENZENE DERIVATIVES; CATALYTIC DOMAIN; CORPUS STRIATUM; DOPAMINE; HUMANS; ISOENZYMES; MODELS, MOLECULAR; MONOAMINE OXIDASE; MONOAMINE OXIDASE INHIBITORS; PIPERAZINES; PIPERIDINES; RATS; STRUCTURE-ACTIVITY RELATIONSHIP;

EID: 84859790954     PISSN: 00222623     EISSN: 15204804     Source Type: Journal    
DOI: 10.1021/jm201692d     Document Type: Article

References (54)

1. Bach, A. W.; Lan, N. C.; Johnson, D. L.; Abell, C. W.; Bembenek, M. E.; Kwan, S. W.; Seeburg, P. H.; Shih, J. C. cDNA cloning of human liver monoamine oxidase A and B: molecular basis of differences in enzymatic properties Proc. Natl. Acad. Sci. U.S.A. 1988, 85, 4934-4938
2. Ito, A.; Kuwahara, T.; Inadome, S.; Sagara, Y. Molecular cloning of a cDNA for rat liver monoamine oxidase B Biochem. Biophys. Res. Commun. 1988, 157, 970-976
3. Kuwahara, T.; Takamoto, S.; Ito, A. Primary structure of rat monoamine oxidase A deduced from cDNA and its expression in rat tissues Agric. Biol. Chem. 1990, 54, 253-257
4. Kwan, S. W.; Abell, C. W. cDNA cloning and sequencing of rat monoamine oxidase A: comparison with the human and bovine enzymes Comp. Biochem. Physiol., Part B 1992, 102, 143-147
5. Johnston, J. P. Some observations upon a new inhibitor of monoamine oxidase in brain tissue Biochem. Pharmacol. 1968, 17, 1285-1297
6. Waldmeier, P. C.; Delini-Stula, A.; Maitre, L. Preferential deamination of dopamine by an A type monoamine oxidase in rat brain Naunyn Schmiedeberg's Arch. Pharmacol. 1976, 292, 9-14
7. Pacher, P.; Kohegyi, E.; Kecskemeti, V.; Furst, S. Current trends in the development of new antidepressants Curr. Med. Chem. 2001, 8, 89-100
8. Weyler, W.; Hsu, Y. P.; Breakefield, X. O. Biochemistry and genetics of monoamine oxidase Pharmacol. Ther. 1990, 47, 391-417
9. Palhagen, S.; Heinonen, E.; Hagglund, J.; Kaugesaar, T.; Maki-Ikola, O.; Palm, R. Selegiline slows the progression of the symptoms of Parkinson disease Neurology 2006, 66, 1200-1206
10. Green, A. R.; Mitchell, B. D.; Tordoff, A. F.; Youdim, M. B. Evidence for dopamine deamination by both type A and type B monoamine oxidase in rat brain in vivo and for the degree of inhibition of enzyme necessary for increased functional activity of dopamine and 5-hydroxytryptamine Br. J. Pharmacol. 1977, 60, 343-349
11. Neff, N. H.; Yang, H. Y.; Fuentes, J. A. Proceedings: the use of selective MAO inhibitor drugs to modify amine metabolism in brain Psychopharmacol. Bull. 1974, 10, 9-10
12. Houslay, M. D.; Tipton, K. F. Multiple forms of monoamine oxidase: fact and artefact Life Sci. 1976, 19, 467-477
13. Demarest, K. T.; Smith, D. J.; Azzaro, A. J. The presence of the type A form of monoamine oxidase within nigrostriatal dopamine-containing neurons J. Pharmacol. Exp. Ther. 1980, 215, 461-468
14. Francis, A.; Pearce, L. B.; Roth, J. A. Cellular localization of MAO A and B in brain: evidence from kainic acid lesions in striatum Brain Res. 1985, 334, 59-64
15. Kato, T.; Dong, B.; Ishii, K.; Kinemuchi, H. Brain dialysis: in vivo metabolism of dopamine and serotonin by monoamine oxidase A but not B in the striatum of unrestrained rats J. Neurochem. 1986, 46, 1277-1282
16. Arbuthnott, G. W.; Fairbrother, I. S.; Butcher, S. P. Dopamine release and metabolism in the rat striatum: an analysis by in vivo brain microdialysis Pharmacol. Ther. 1990, 48, 281-293
17. Butcher, S. P.; Fairbrother, I. S.; Kelly, J. S.; Arbuthnott, G. W. Effects of selective monoamine oxidase inhibitors on the in vivo release and metabolism of dopamine in the rat striatum J. Neurochem. 1990, 55, 981-988
18. Fulton, B.; Benfield, P. Moclobemide. An update of its pharmacological properties and therapeutic use Drugs 1996, 52, 450-474
19. Livingston, M. G.; Livingston, H. M. Monoamine oxidase inhibitors. An update on drug interactions Drug Saf. 1996, 14, 219-227
20. Mann, J. J.; Aarons, S. F.; Frances, A. J.; Brown, R. D. Studies of selective and reversible monoamine oxidase inhibitors J. Clin. Psychiatry 1984, 45, 62-66
21. Anderson, M. C.; Hasan, F.; McCrodden, J. M.; Tipton, K. F. Monoamine oxidase inhibitors and the cheese effect Neurochem. Res. 1993, 18, 1145-1149
22. Blackwell, B.; Marley, E.; Price, J.; Taylor, D. Hypertensive interactions between monoamine oxidase inhibitors and foodstuffs Br. J. Psychiatry 1967, 113, 349-365
23. Lotufo-Neto, F.; Trivedi, M.; Thase, M. E. Meta-analysis of the reversible inhibitors of monoamine oxidase type A moclobemide and brofaromine for the treatment of depression Neuropsychopharmacology 1999, 20, 226-247
24. Binda, C.; Hubalek, F.; Li, M.; Herzig, Y.; Sterling, J.; Edmondson, D. E.; Mattevi, A. Binding of rasagiline-related inhibitors to human monoamine oxidases: a kinetic and crystallographic analysis J. Med. Chem. 2005, 48, 8148-8154
25. Gallardo-Godoy, A.; Fierro, A.; McLean, T. H.; Castillo, M.; Cassels, B. K.; Reyes-Parada, M.; Nichols, D. E. Sulfur-substituted alpha-alkyl phenethylamines as selective and reversible MAO-A inhibitors: biological activities, CoMFA analysis, and active site modeling J. Med. Chem. 2005, 48, 2407-2419
26. Miller, J. R.; Edmondson, D. E. Structure-activity relationships in the oxidation of para-substituted benzylamine analogues by recombinant human liver monoamine oxidase A Biochemistry 1999, 38, 13670-13683
27. Nandigama, R. K.; Edmondson, D. E. Structure-activity relations in the oxidation of phenethylamine analogues by recombinant human liver monoamine oxidase A Biochemistry 2000, 39, 15258-15265
28. Scorza, M. C.; Carrau, C.; Silveira, R.; Zapata-Torres, G.; Cassels, B. K.; Reyes-Parada, M. Monoamine oxidase inhibitory properties of some methoxylated and alkylthio amphetamine derivatives: structure-activity relationships Biochem. Pharmacol. 1997, 54, 1361-1369
29. Walker, M. C.; Edmondson, D. E. Structure-activity relationships in the oxidation of benzylamine analogues by bovine liver mitochondrial monoamine oxidase B Biochemistry 1994, 33, 7088-7098
30. De Colibus, L.; Li, M.; Binda, C.; Lustig, A.; Edmondson, D. E.; Mattevi, A. Three-dimensional structure of human monoamine oxidase A (MAO A): relation to the structures of rat MAO A and human MAO B Proc. Natl. Acad. Sci. U.S.A. 2005, 102, 12684-12689
31. Edmondson, D. E.; DeColibus, L.; Binda, C.; Li, M.; Mattevi, A. New insights into the structures and functions of human monoamine oxidases A and B J. Neural Transm. 2007, 114, 703-705
32. Ma, J.; Yoshimura, M.; Yamashita, E.; Nakagawa, A.; Ito, A.; Tsukihara, T. Structure of rat monoamine oxidase A and its specific recognitions for substrates and inhibitors J. Mol. Biol. 2004, 338, 103-114
33. Dyhring, T.; Nielsen, E. O.; Sonesson, C.; Pettersson, F.; Karlsson, J.; Svensson, P.; Christophersen, P.; Waters, N. The dopaminergic stabilizers pridopidine (ACR16) and (-)-OSU6162 display dopamine D(2) receptor antagonism and fast receptor dissociation properties Eur. J. Pharmacol. 2010, 628, 19-26
34. Pettersson, F.; Ponten, H.; Waters, N.; Waters, S.; Sonesson, C. Synthesis and evaluation of a set of 4-phenylpiperidines and 4-phenylpiperazines as D2 receptor ligands and the discovery of the dopaminergic stabilizer 4-[3-(methylsulfonyl)phenyl]-1-propylpiperidine (huntexil, pridopidine, ACR16) J. Med. Chem. 2010, 53, 2510-2520
35. Di Santo, R.; Costi, R.; Roux, A.; Artico, M.; Befani, O.; Meninno, T.; Agostinelli, E.; Palmegiani, P.; Turini, P.; Cirilli, R.; Ferretti, R.; Gallinella, B.; La Torre, F. Design, synthesis, and biological activities of pyrrolylethanoneamine derivatives, a novel class of monoamine oxidases inhibitors J. Med. Chem. 2005, 48, 4220-4223
36. Sterling, J.; Herzig, Y.; Goren, T.; Finkelstein, N.; Lerner, D.; Goldenberg, W.; Miskolczi, I.; Molnar, S.; Rantal, F.; Tamas, T.; Toth, G.; Zagyva, A.; Zekany, A.; Finberg, J.; Lavian, G.; Gross, A.; Friedman, R.; Razin, M.; Huang, W.; Krais, B.; Chorev, M.; Youdim, M. B.; Weinstock, M. Novel dual inhibitors of AChE and MAO derived from hydroxy aminoindan and phenethylamine as potential treatment for Alzheimer's disease J. Med. Chem. 2002, 45, 5260-5279
37. Son, S. Y.; Ma, J.; Kondou, Y.; Yoshimura, M.; Yamashita, E.; Tsukihara, T. Structure of human monoamine oxidase A at 2.2-Ã resolution: the control of opening the entry for substrates/inhibitors Proc. Natl. Acad. Sci. U.S.A. 2008, 105, 5739-5744
38. Halgren, T. A. MMFF VII. Characterization of MMFF94, MMFF94s, and other widely available force fields for conformational energies and for intermolecular-interaction energies and geometries J. Comput. Chem. 1999, 20, 730-748
39. Halgren, T. A. MMFF VI. MMFF94s option for energy minimization studies J. Comput. Chem. 1999, 20, 720-729
40. Wojciechowski, M.; Lesyng, B. Generalized Born model:analysis, refinement, and applications to proteins J. Phys. Chem. B 2004, 108, 18368-18376
41. Molecular Operating Environment (MOE), version 2009.10; Chemical Computing Group Inc.: Montreal, Canada, 2009.
42. Connolly, M. L. Solvent-accessible surfaces of proteins and nucleic acids Science 1983, 221, 709-713
43. Sethian, J. A. A fast marching level set method for monotonically advancing fronts Proc. Natl. Acad. Sci. U.S.A. 1996, 93, 1591-1595
44. Wildman, S. A.; Crippen, G. M. Prediction of physicochemical parameters by atomic contributions J. Chem. Inf. Comput. Sci. 1999, 39, 868-873
45. Heikkila, R. E.; Hess, A.; Duvoisin, R. C. Dopaminergic neurotoxicity of 1-methyl-4-phenyl-1,2,5,6-tetrahydropyridine (MPTP) in the mouse: relationships between monoamine oxidase, MPTP metabolism and neurotoxicity Life Sci. 1985, 36, 231-236
46. Kula, N. S.; Baldessarini, R. J.; Murphy, F.; Neumeyer, J. L. Substituted phenylpiperidines and phenylpyridines as reversible selective inhibitors of monoamine oxidase type A in rodent brain and liver Biochem. Pharmacol. 1988, 37, 763-766
47. Heikkila, R. E.; Manzino, L.; Cabbat, F. S.; Duvoisin, R. C. Effects of 1-methyl-4-phenyl-1,2,3,6-tetrahydropyridine (MPTP) and several of its analogues on the dopaminergic nigrostriatal pathway in mice Neurosci. Lett. 1985, 58, 133-137
48. Maret, G.; el Tayar, N.; Carrupt, P. A.; Testa, B.; Jenner, P.; Baird, M. Toxication of MPTP (1-methyl-4-phenyl-1,2,3,6-tetrahydropyridine) and analogs by monoamine oxidase. A structure-reactivity relationship study Biochem. Pharmacol. 1990, 40, 783-792
49. Langston, J. W.; Irwin, I.; Langston, E. B.; Forno, L. S. The importance of the 4-5 double bond for neurotoxicity in primates of the pyridine derivative MPTP Neurosci. Lett. 1984, 50, 289-294
50. Youngster, S. K.; McKeown, K. A.; Jin, Y. Z.; Ramsay, R. R.; Heikkila, R. E.; Singer, T. P. Oxidation of analogs of 1-methyl-4-phenyl-1,2,3,6- tetrahydropyridine by monoamine oxidases A and B and the inhibition of monoamine oxidases by the oxidation products J. Neurochem. 1989, 53, 1837-1842
51. Trygg, J.; Wold, S. Orthogonal projections to latent structures (O-PLS) J. Chemom. 2002, 16, 119-128
52. Reniers, J.; Robert, S.; Frederick, R.; Masereel, B.; Vincent, S.; Wouters, J. Synthesis and evaluation of beta-carboline derivatives as potential monoamine oxidase inhibitors Bioorg. Med. Chem. 2010, 19, 134-144
53. Campbell, I. C.; Robinson, D. S.; Lovenberg, W.; Murphy, D. L. The effects of chronic regimens of clorgyline and pargyline on monoamine metabolism in the rat brain J. Neurochem. 1979, 32, 49-55
54. Braestrup, C.; Andersen, H.; Randrup, A. The monoamine oxidase B inhibitor deprenyl potentiates phenylethylamine behaviour in rats without inhibition of catecholamine metabolite formation Eur. J. Pharmacol. 1975, 34, 181-187