Naphthylisopropylamine and N-benzylamphetamine derivatives as monoamine oxidase inhibitors

Bioorganic and Medicinal Chemistry

Volumn 17, Issue 6, 2009, Pages 2452-2460

  Vilches Herrera, Marcelo ^a   Miranda Sepúlveda, Juan ^b   Rebolledo Fuentes, Marco ^a,c   Fierro, Angélica ^b,c   Lühr, Susan ^a   Iturriaga Vasquez, Patricio ^a,c   Cassels, Bruce K ^a,c   Reyes Parada, Miguel ^b,c  

^a UNIVERSITY OF CHILE   (Chile)

^b UNIVERSIDAD DE SANTIAGO DE CHILE   (Chile)

^c Iniciativa Cientifica Milenio Santiago   (Chile)

Author keywords

Amphetamine derivatives; Docking; MAO inhibitors; Monoamine oxidase; Naphthylisopropylamine derivatives; PAL 287

Indexed keywords

(6 METHOXY 2 NAPHTHYL) 2 AMINOPROPANE; 2 NAPHTHYLISOPROPYLAMINE; 4 METHOXYAMPHETAMINE; 4 METHYLTHIOAMPHETAMINE; AMPHETAMINE; AMPHETAMINE DERIVATIVE; MONOAMINE OXIDASE INHIBITOR; N BENZYL 4 METHYLTHIOAMPHETAMINE DERIVATIVE; NAPHTHYLISOPROPYLAMINE DERIVATIVE; PAL 284; PROPYLAMINE; UNCLASSIFIED DRUG;

ARTICLE; BENZYLATION; DRUG BINDING; DRUG POTENCY; DRUG STRUCTURE; DRUG SYNTHESIS; ENZYME INHIBITION; MOLECULAR DOCKING; NONHUMAN; RAT; STRUCTURE ANALYSIS;

ANIMALS; BENZPHETAMINE; MAGNETIC RESONANCE SPECTROSCOPY; MODELS, MOLECULAR; MONOAMINE OXIDASE INHIBITORS; NAPHTHALENES; PROPYLAMINES; RATS;

EID: 62149117987     PISSN: 09680896     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.bmc.2009.01.074     Document Type: Article

References (44)

1. Cesura A.M., and Pletscher A. Prog. Drug Res. 38 (1992) 171
2. Youdim M.B.H., Edmondson D., and Tipton K.F. Nat. Rev. Neurosci. 7 (2006) 295
3. Binda C., Newton-Vinson P., Hubálek F., Edmondson D.E., and Mattevi A. Nat. Struct. Biol. 9 (2002) 22
4. Ma J., Yoshimura M., Yamashita E., Nakagawa A., Ito A., and Tsukihara T. J. Mol. Biol. 338 (2004) 103
5. De Colibus L., Li M., Binda C., Lustig A., Edmondson D.E., and Mattevi A. Proc. Natl. Acad. Sci. U.S.A. 102 (2005) 12684
6. Son S.Y., Ma J., Kondou Y., Yoshimura M., Yamashita E., and Tsukihara T. Proc. Natl. Acad. Sci. U.S.A. 105 (2008) 5739
7. Yelekçi K., Karahan O., and Toprakçi M. J. Neural Transm. 114 (2007) 725
8. La Regina G., Silvestri R., Artico M., Lavecchia A., Novellino E., Befani O., Turini P., and Agostinelli E. J. Med. Chem. 50 (2007) 922
9. Chimenti F., Maccioni E., Secci D., Bolasco A., Chimenti P., Granese A., Befani O., Turini P., Alcaro S., Ortuso F., Cardia M.C., and Distinto S. J. Med. Chem. 50 (2007) 707
10. Braun G.H., Jorge D.M., Ramos H.P., Alves R.M., da Silva V.B., Giuliatti S., Sampaio S.V., Taft C.A., and Silva C.H. J. Biomol. Struct. Dyn. 25 (2008) 347
11. Florvall L., Ask A.L., Ögren S.O., and Ross S.B. J. Med. Chem. 21 (1978) 56
12. Scorza M.C., Carrau C., Silveira R., Zapata-Torres G., Cassels B.K., and Reyes-Parada M. Biochem. Pharmacol. 54 (1997) 1361
13. Gallardo-Godoy A., Fierro A., McLean T.H., Castillo M., Cassels B.K., Reyes-Parada M., and Nichols D.E. J. Med. Chem. 48 (2005) 2407
14. Vallejos G., Rezende M.C., and Cassels B.K. J. Comput.-Aided Mol. Des. 16 (2002) 95
15. Fierro A., Osorio-Olivares M., Cassels B.K., Edmondson D.E., Sepulveda-Boza S., and Reyes-Parada M. Bioorg. Med. Chem. 15 (2007) 5198
16. Reyes-Parada M., Fierro A., Iturriaga-Vásquez P., and Cassels B.K. Curr. Enz. Inhib. 1 (2005) 85
17. Chimenti F., Secci D., Bolasco A., Chimenti P., Granese A., Carradori S., Befani O., Turini P., Alcaro S., and Ortuso F. Bioorg. Med. Chem. Lett. 16 (2006) 4135
18. Jones T.Z., Fleming P., Eyermann C.J., Gravestock M.B., and Ramsay R.R. Biochem. Pharmacol. 70 (2005) 407
19. Matsuzawa N., and Dixon D.A. J. Phys. Chem. 96 (1992) 6241
20. Boschi R., Clar E., and Schmidt W. J. Chem. Phys. 60 (1974) 4406
21. Mantle T.J., Tipton K.F., and Garrett N.J. Biochem. Pharmacol. 25 (1976) 2073
22. Fowler C.J., and Oreland L. J. Pharm. Pharmacol. 33 (1981) 403
23. Leonardi E.T.K., and Azmitia E.C. Neuropsychopharmacology 10 (1994) 231
24. Hurtado-Guzmán C., Fierro A., Iturriaga-Vásquez P., Sepúlveda-Boza S., Cassels B.K., and Reyes-Parada M. J. Enz. Inhib. Med. Chem. 18 (2003) 339
25. Morón J.A., Campillo M., Pérez V., Unzeta M., and Pardo L. J. Med. Chem. 43 (2000) 1684
26. Jones T.Z., Giurato L., Guccione S., and Ramsay R.R. FEBS J. 274 (2007) 1567
27. Vallejos G., Fierro A., Rezende M.C., Sepúlveda-Boza S., and Reyes-Parada M. Bioorg. Med. Chem. 13 (2005) 4450
28. Rothman R.B., Blough B.E., Woolverton W.L., Anderson K.G., Negus S.S., Mello N.K., Roth B.L., and Baumann M.H. J. Pharmacol. Exp. Ther. 313 (2005) 1361
29. Rothman R.B., Blough B.E., and Baumann M.H. AAPS J. 9 (2007) E1
30. Markow A., Kosten T.R., and Koob G.F. Neuropsychopharmacology 18 (1998) 135
31. Shulgin A.T., and Shulgin A. PIHKAL a Chemical Love Story (1992), Transform Press, Berkeley, CA
32. Bailey K., Beckstead H.D., Legault D., and Verner D. J. Assoc. Off. Anal. Chem. 57 (1974) 1134
33. Kölliker S., and Oehme M. Anal. Bioanal. Chem. 378 (2004) 1294
34. Prabhakar C., Bakki Reddy G., Maheedhara Reddy Ch., Nageshwar D., Sivalakashm Devi A., Moses Babu J., Vyas K., Sarma M.R., and Om Reddy G. Org. Process Res. Dev. 3 (1999) 121
35. Koelsch, C. F. Org. Synth., 1955, 3, 132, www.orgsyn.org on line.
36. Wolfers H., Kraatz U., and Korte F. Synthesis 1 (1975) 43
37. Kwart H., and Evans E.R. J. Org. Chem. 31 (1966) 410
38. Newman M.S., and Karnes H.A. J. Org. Chem. 31 (1966) 3980
39. Frieman L., and Schechter H. J. Org. Chem. 26 (1961) 2522
40. Miller A.E.G., Biss J.W., and Schwartzman L.H. J. Org. Chem. 24 (1959) 627
41. Cheng Y.C., and Prusoff W.H. Biochem. Pharmacol. 22 (1973) 3099
42. Morris G.M., Goodsell D.S., Halliday R.S., Huey R., Hart W.E., Belew R.K., and Olson A.J. J. Comput. Chem. 19 (1998) 1639
43. Insight II and Discover, User Guide, Accelrys, San Diego, CA, USA, 1998.
44. Bayly C.I., Cieplak P., Cornell W.D., and Kollman P.A. J. Phys. Chem. 97 (1993) 10269