A novel series of 6-substituted 3-(pyrrolidin-1-ylmethyl)chromen-2-ones as selective monoamine oxidase (MAO) A inhibitors

European Journal of Medicinal Chemistry

Volumn 73, Issue , 2014, Pages 177-186

  Mattsson, Cecilia ^a   Svensson, Peder ^a,b   Sonesson, Clas ^a  

^a Carlsson Research AB   (Sweden)

^b ASTRAZENECA R AND D   (Sweden)

Author keywords

5 HIAA; Coumarin; DOPAC; Molecular modeling; Monoamine oxidase A inhibitor

Indexed keywords

2 BENZYLOXY 5 BUTOXY BENZALDEHYDE; 2 BENZYLOXYBENZALDEHYDE; 3 O METHYLDOPAMINE; 3,4 DIHYDROXYPHENYLACETIC ACID; 5 BUTOXY 2 HYDROXY BENZALDEHYDE; 5 HYDROXYINDOLEACETIC ACID; 6 AMINO 3 (PYRROLIDIN 1 YLMETHYL)CHROMEN 2 ONE; 6 BUTOXY 3 (ETHYLAMINOMETHYL)CHROMEN 2 ONE; AMINE OXIDASE (FLAVIN CONTAINING) ISOENZYME A; AMINE OXIDASE (FLAVIN CONTAINING) ISOENZYME B; COUMARIN DERIVATIVE; METHYL 2 [(2 BENZYLOXY 5 BUTOXY PHENYL)HYDROXY METHYL]PROP 2 ENOATE; MOCLOBEMIDE; MONOAMINE OXIDASE B INHIBITOR; MONOAMINE OXIDASE INHIBITOR; SELEGILINE; TRANYLCYPROMINE; UNCLASSIFIED DRUG;

ANIMAL EXPERIMENT; ANIMAL TISSUE; ARTICLE; COMPETITIVE INHIBITION; CONTROLLED STUDY; DRUG DETERMINATION; DRUG POTENCY; DRUG SELECTIVITY; DRUG SOLUBILITY; DRUG STRUCTURE; DRUG SYNTHESIS; ENZYME INHIBITION; IC 50; IN VIVO STUDY; NONHUMAN; RAT; SUBSTITUTION REACTION;

5-HIAA; COUMARIN; DOPAC; DOPAMINE D(2) ANTAGONIST; MOLECULAR MODELING; MONOAMINE OXIDASE A INHIBITOR;

ANIMALS; BINDING SITES; CHROMONES; CORPUS STRIATUM; HUMANS; MICRODIALYSIS; MODELS, MOLECULAR; MOLECULAR STRUCTURE; MONOAMINE OXIDASE; MONOAMINE OXIDASE INHIBITORS; NEUROTRANSMITTER AGENTS; PROTEIN BINDING; RATS; SOLUBILITY; STRUCTURE-ACTIVITY RELATIONSHIP;

EID: 84891770716     PISSN: 02235234     EISSN: 17683254     Source Type: Journal    
DOI: 10.1016/j.ejmech.2013.11.035     Document Type: Article

References (72)

1. J. Duncan, S. Johnson, and X.M. Ou Monoamine oxidases in major depressive disorder and alcoholism Drug Discov. Ther. 6 2012 112 122
2. J.P. Johnston Some observations upon a new inhibitor of monoamine oxidase in brain tissue Biochem. Pharmacol. 17 1968 1285 1297
3. A.W. Bach, N.C. Lan, D.L. Johnson, C.W. Abell, M.E. Bembenek, S.W. Kwan, P.H. Seeburg, and J.C. Shih cDNA cloning of human liver monoamine oxidase A and B: molecular basis of differences in enzymatic properties Proc. Nat. Acad. Sci. 85 1988 4934 4938
4. M. Bortolato, K. Chen, and J.C. Shih Monoamine oxidase inactivation: from pathophysiology to therapeutics Adv. Drug Deliv. Rev. 60 2008 1527 1533
5. F. Lopez-Munoz, C. Alamo, G. Juckel, and H.J. Assion Half a century of antidepressant drugs: on the clinical introduction of monoamine oxidase inhibitors, tricyclics, and tetracyclics. Part I: monoamine oxidase inhibitors J. Clin. Psychopharmacol. 27 2007 555 559
6. P. Riederer, and G. Laux MAO-inhibitors in Parkinson's disease Exp. Neurobiol. 20 2011 1 17
7. J.J. Chen, and D.M. Swope Pharmacotherapy for Parkinson's disease Pharmacotherapy 27 2007 161S 173S
8. P. Riederer, W. Danielczyk, and E. Grunblatt Monoamine oxidase-b inhibition in Alzheimer's disease Neurotoxicology 25 2004 271 277
9. F. Stocchi, R. Borgohain, M. Onofrj, A.H. Schapira, M. Bhatt, V. Lucini, R. Giuliani, and R. Anand A randomized, double-blind, placebo-controlled trial of safinamide as add-on therapy in early Parkinson's disease patients Mov. Disord. 27 2012 106 112
10. M.B. Youdim, and Y.S. Bakhle Monoamine oxidase: isoforms and inhibitors in Parkinson's disease and depressive illness Br. J. Pharmacol. 147 Suppl. 1 2006 S287 S296
11. M.B.H. Youdim, O. Bar Am, M. Yogev-Falach, O. Weinreb, W. Maruyama, M. Naoi, and T. Amit Rasagiline: neurodegeneration, neuroprotection, and mitochondrial permeability transition J. Neurosci. Res. 79 2005 172 179
12. F. Lotufo-Neto, M. Trivedi, and M.E. Thase Meta-analysis of the reversible inhibitors of monoamine oxidase type A moclobemide and brofaromine for the treatment of depression Neuropsychopharmacology 20 1999 226 247
13. W. Haefely, W.P. Burkard, A.M. Cesura, R. Kettler, H.P. Lorez, J.R. Martin, J.G. Richards, R. Scherschlicht, and M. Da Prada Biochemistry and pharmacology of moclobemide, a prototype RIMA Psychopharmacology (Berlin) 106 Suppl. 1992 S6 S14
14. I. Berlin, R. Zimmer, H.M. Thiede, C. Payan, T. Hergueta, L. Robin, and A.J. Puech Comparison of the monoamine oxidase inhibiting properties of two reversible and selective monoamine oxidase-A inhibitors moclobemide and toloxatone, and assessment of their effect on psychometric performance in healthy subjects Br. J. Clin. Pharmacol. 30 1990 805 816
15. F. Gentili, N. Pizzinat, C. Ordener, S. Marchal-Victorion, A. Maurel, R. Hofmann, P. Renard, P. Delagrange, M. Pigini, A. Parini, and M. Giannella 3-[5-(4,5-dihydro-1H-imidazol-2-yl)-furan-2-yl]phenylamine (amifuraline), a promising reversible and selective peripheral MAO-A inhibitor J. Med. Chem. 49 2006 5578 5586
16. J.S. Fowler, J. Logan, A.J. Azzaro, R.M. Fielding, W. Zhu, A.K. Poshusta, D. Burch, B. Brand, J. Free, M. Asgharnejad, G.J. Wang, F. Telang, B. Hubbard, M. Jayne, P. King, P. Carter, S. Carter, Y. Xu, C. Shea, L. Muench, D. Alexoff, E. Shumay, M. Schueller, D. Warner, and K. Apelskog-Torres Reversible inhibitors of monoamine oxidase-A (RIMAs): robust, reversible inhibition of human brain MAO-A by CX157 Neuropsychopharmacology 35 2010 623 631
17. J.D. Amsterdam, and J. Shults MAOI efficacy and safety in advanced stage treatment-resistant depression - a retrospective study J. Affective Dis. 89 2005 183 188
18. A.M. Helguera, G. Perez-Machado, M.N. Cordeiro, and F. Borges Discovery of MAO-B inhibitors - present status and future directions part I: oxygen heterocycles and analogs Mini Rev. Med. Chem. 12 2012 907 919
19. B. Rendenbach-Muller, R. Schlecker, M. Traut, and H. Weifenbach Synthesis of coumarins as subtype-selective inhibitors of monoamine oxidase Bioorg. Med. Chem. Lett. 4 1994 1195 1198
20. C. Gnerre, M. Catto, F. Leonetti, P. Weber, P.A. Carrupt, C. Altomare, A. Carotti, and B. Testa Inhibition of monoamine oxidases by functionalized coumarin derivatives: biological activities, QSARs, and 3D-QSARs J. Med. Chem. 43 2000 4747 4758
21. L. Novaroli, A. Daina, E. Favre, J. Bravo, A. Carotti, F. Leonetti, M. Catto, P.A. Carrupt, and M. Reist Impact of species-dependent differences on screening, design, and development of MAO B inhibitors J. Med. Chem. 49 2006 6264 6272
22. A. Carotti, A. Carrieri, S. Chimichi, M. Boccalini, B. Cosimelli, C. Gnerre, A. Carotti, P.-A. Carrupt, and B. Testa Natural and synthetic geiparvarins are strong and selective MAO-B inhibitors. synthesis and SAR studies Bioorg. Med. Chem. Lett. 12 2002 3551 3555
23. F. Chimenti, D. Secci, A. Bolasco, P. Chimenti, B. Bizzarri, A. Granese, S. Carradori, M. Yanez, F. Orallo, F. Ortuso, and S. Alcaro Synthesis, molecular modeling, and selective inhibitory activity against human monoamine oxidases of 3-carboxamido-7-substituted coumarins J. Med. Chem. 52 2009 1935 1942
24. M.J. Matos, D. Vina, E. Quezada, C. Picciau, G. Delogu, F. Orallo, L. Santana, and E. Uriarte A new series of 3-phenylcoumarins as potent and selective MAO-B inhibitors Bioorg. Med. Chem. Lett. 19 2009 3268 3270
25. D. Secci, S. Carradori, A. Bolasco, P. Chimenti, M. Yanez, F. Ortuso, and S. Alcaro Synthesis and selective human monoamine oxidase inhibition of 3-carbonyl, 3-acyl, and 3-carboxyhydrazido coumarin derivatives Eur. J. Med. Chem. 46 2011 4846 4852
26. M.J. Matos, S. Vazquez-Rodriguez, E. Uriarte, L. Santana, and D. Vina MAO inhibitory activity modulation: 3-Phenylcoumarins versus 3-benzoylcoumarins Bioorg. Med. Chem. Lett. 21 2011 4224 4227
27. M.J. Matos, C. Teran, Y. Perez-Castillo, E. Uriarte, L. Santana, and D. Vina Synthesis and study of a series of 3-arylcoumarins as potent and selective monoamine oxidase B inhibitors J. Med. Chem. 54 2011 7127 7137
28. L. Santana, H. Gonzalez-Diaz, E. Quezada, E. Uriarte, M. Yanez, D. Vina, and F. Orallo Quantitative structure-activity relationship and complex network approach to monoamine oxidase A and B inhibitors J. Med. Chem. 51 2008 6740 6751
29. O.M. Abdelhafez, K.M. Amin, H.I. Ali, M.M. Abdalla, and R.Z. Batran Synthesis of new 7-oxycoumarin derivatives as potent and selective monoamine oxidase a inhibitors J. Med. Chem. 55 2012 10424 10436
30. O.M. Abdelhafez, K.M. Amin, H.I. Ali, M.M. Abdalla, and R.Z. Batran Monoamine oxidase A and B inhibiting effect and molecular modeling of some synthesized coumarin derivatives Neurochem. Int. 62 2012 198 209
31. F. Chimenti, D. Secci, A. Bolasco, P. Chimenti, A. Granese, O. Befani, P. Turini, S. Alcaro, and F. Ortuso Inhibition of monoamine oxidases by coumarin-3-acyl derivatives: biological activity and computational study Bioorg. Med. Chem. Lett. 14 2004 3697 3703
32. R.E. Mewshaw, J. Kavanagh, G. Stack, K.L. Marquis, X. Shi, M.Z. Kagan, M.B. Webb, A.H. Katz, A. Park, Y.H. Kang, M. Abou-Gharbia, R. Scerni, T. Wasik, L. Cortes-Burgos, T. Spangler, J.A. Brennan, M. Piesla, H. Mazandarani, M.I. Cockett, R. Ochalski, J. Coupet, and T.H. Andree New generation dopaminergic agents. 1. Discovery of a novel scaffold which embraces the D2 agonist pharmacophore. Structure activity relationships of a series of 2-(aminomethyl)chromans J. Med. Chem. 40 1997 4235 4256
33. P.T. Kaye, and M.A. Musa Application of Baylis-Hillman methodology in the synthesis of coumarin derivatives Synth. Commun. 33 2003 1755 1770
34. R. Aldred, R. Johnston, D. Levin, and J. Neilan Magnesium-mediated ortho-specific formylation and formaldoximation of phenols J. Chem. Soc. Perkin Trans. 1 Org. Bio-Org. Chem. (1972-1999) 13 1994 1823 1831
35. S.H. Ahn, H.N. Lim, and K.J. Lee Application of the acetate of Baylis-Hillman adducts of salicylaldehydes in the synthesis of methyl 2-oxo-2,3-dihydrobenzo[b]oxepine-4-carboxylates J. Heterocycl. Chem. 45 2008 1701 1706
36. V.K. Aggarwal, I. Emme, and S.Y. Fulford Correlation between pKa and reactivity of quinuclidine-based catalysts in the Baylis-Hillman reaction: discovery of quinuclidine as optimum catalyst leading to substantial enhancement of scope J. Org. Chem. 68 2003 692 700
37. P.T. Kaye The Baylis-Hillman entrée to heterocyclic systems - the Rhodes contribution S. Afr. J. Sci. 100 2004 545 548
38. R.G. Dyer, and K.D. Turnbull Hydrolytic stabilization of protected p-hydroxybenzyl halides designed as latent quinone methide precursors J. Org. Chem. 64 1999 7988 7995
39. T.T. Sakai, and D.V. Santi Hydrolysis of hydroxybenzotrifluorides and fluorinated uracil derivatives. General mechanism for carbon-fluorine bond labilization J. Med. Chem. 16 1973 1079 1084
40. H. Geneste, and B. Schäfer 2-Substituted 4-(trifluoromethyl)phenols by directed ortho-lithiation Synthesis 15 2001 2259 2262
41. C.-N. Huang, P.-Y. Kuo, C.-H. Lin, and D.-Y. Yang Synthesis and characterization of 2H-pyrano[3,2-c]coumarin derivatives and their photochromic and redox properties Tetrahedron 63 2007 10025 10033
42. K.M. Amin, F.M. Awadalla, A.A.M. Eissa, S.M. Abou-Seri, and G.S. Hassan Design, synthesis and vasorelaxant evaluation of novel coumarin-pyrimidine hybrids Bioorg. Med. Chem. 19 2011 6087 6097
43. P.T. Kaye, and M.A. Musa Regioselectivity of reactions of nitrogen and carbon nucleophiles with coumarin derivatives Synth. Commun. 34 2004 3409 3417
44. Z. Yan, G.W. Caldwell, B. Zhao, and A.B. Reitz A high-throughput monoamine oxidase inhibition assay using liquid chromatography with tandem mass spectrometry Rapid Commun. Mass Spectrom. 18 2004 834 840
45. T. Dyhring, E.O. Nielsen, C. Sonesson, F. Pettersson, J. Karlsson, P. Svensson, P. Christophersen, and N. Waters The dopaminergic stabilizers pridopidine (ACR16) and (-)-OSU6162 display dopamine D(2) receptor antagonism and fast receptor dissociation properties Eur. J. Pharmacol. 628 2010 19 26
46. J.G. Mulheron, S.J. Casanas, J.M. Arthur, M.N. Garnovskaya, T.W. Gettys, and J.R. Raymond Human 5-HT1A receptor expressed in insect cells activates endogenous G(o)-like G protein(s) J. Biol. Chem. 269 1994 12954 12962
47. D.W. Bonhaus, C. Bach, A. DeSouza, F.H. Salazar, B.D. Matsuoka, P. Zuppan, H.W. Chan, and R.M. Eglen The pharmacology and distribution of human 5-hydroxytryptamine2B (5-HT2B) receptor gene products: comparison with 5-HT2A and 5-HT2C receptors Br. J. Pharmacol. 115 1995 622 628
48. P. Greengrass, and R. Bremmer Binding characteristics of 3H-prazosin to rat brain α-adrenergic receptors Eur. J. Med. Pharmacol. 55 1979 323 326
49. T. Nyronen, M. Pihlavisto, J.M. Peltonen, A.M. Hoffren, M. Varis, T. Salminen, S. Wurster, A. Marjamaki, L. Kanerva, E. Katainen, L. Laaksonen, J.M. Savola, M. Scheinin, and M.S. Johnson Molecular mechanism for agonist-promoted alpha(2A)-adrenoceptor activation by norepinephrine and epinephrine Mol. Pharmacol. 59 2001 1343 1354
50. T.R. Miller, D.G. Witte, L.M. Ireland, C.H. Kang, J.M. Roch, J.N. Masters, T.A. Esbenshade, and A.A. Hancock Analysis of apparent noncompetitive responses to competitive H1-histamine receptor antagonists in fluorescent Imaging plate reader-based calcium assays J. Biomol. Screening 4 1999 249 258
51. Z.B. Pristupa, J.M. Wilson, B.J. Hoffman, S.J. Kish, and H.B. Niznik Pharmacological heterogeneity of the cloned and native human dopamine transporter: disassociation of [3H]WIN 35,428 and [3H]GBR 12,935 binding Mol. Pharmacol. 45 1994 125 135
52. M. Tatsumi, K. Jansen, R.D. Blakely, and E. Richelson Pharmacological profile of neuroleptics at human monoamine transporters Eur. J. Pharmacol. 368 1999 277 283
53. T. Pacholczyk, R.D. Blakely, and S.G. Amara Expression cloning of a cocaine-and antidepressant-sensitive human noradrenaline transporter Nature 350 1991 350 354
54. N. Waters, S. Lagerkvist, L. Löfberg, M. Piercey, and A. Carlsson The dopamine D3 receptor and autoreceptor preferring antagonists (+)-AJ76 and (+)-UH232; a microdialysis study Eur. J. Pharmacol. 242 1993 151 163
55. Schrödinger Suite 2012.04: Protein Preparation Wizard, Epic Version 2.3; Impact Version 5.8; Prime Version 3.1 2012 Schrödinger, LLC New York, NY
56. S.Y. Son, J. Ma, Y. Kondou, M. Yoshimura, E. Yamashita, and T. Tsukihara Structure of human monoamine oxidase A at 2.2-A resolution: the control of opening the entry for substrates/inhibitors Proc. Natl. Acad. Sci. U. S. A. 105 2008 5739 5744
57. D. Shivakumar, J. Williams, Y. Wu, W. Damm, J. Shelley, and W. Sherman Prediction of absolute solvation free energies using molecular dynamics free energy perturbation and the OPLS force field J. Chem. Theory Comput. 6 2010 1509 1519
58. R.A. Friesner, R.B. Murphy, M.P. Repasky, L.L. Frye, J.R. Greenwood, T.A. Halgren, P.C. Sanschagrin, and D.T. Mainz Extra precision glide: docking and scoring incorporating a model of hydrophobic enclosure for protein-ligand complexes J. Med. Chem. 49 2006 6177 6196
59. R.A. Friesner, J.L. Banks, R.B. Murphy, T.A. Halgren, J.J. Klicic, D.T. Mainz, M.P. Repasky, E.H. Knoll, M. Shelley, J.K. Perry, D.E. Shaw, P. Francis, and P.S. Shenkin Glide: a new approach for rapid, accurate docking and scoring. 1. Method and assessment of docking accuracy J. Med. Chem. 47 2004 1739 1749
60. Schrödinger Suite 2012.04: LigPrep 2.5 User Manual 2012 Schrödinger, LLC New York, NY
61. P. Seeman Brain dopamine receptors Pharmacol. Rev. 32 1980 229 313
62. D.E. Edmondson, C. Binda, J. Wang, A.K. Upadhyay, and A. Mattevi Molecular and mechanistic properties of the membrane-bound mitochondrial monoamine oxidases Biochemistry 48 2009 4220 4230
63. L. De Colibus, M. Li, C. Binda, A. Lustig, D.E. Edmondson, and A. Mattevi 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. 102 2005 12684 12689
64. F. Pettersson, P. Svensson, S. Waters, N. Waters, and C. Sonesson Synthesis and evaluation of a set of para-substituted 4-phenylpiperidines and 4-phenylpiperazines as monoamine oxidase (MAO) inhibitors J. Med. Chem. 55 2012 3242 3249
65. A. Gallardo-Godoy, A. Fierro, T.H. McLean, M. Castillo, B.K. Cassels, M. Reyes-Parada, and D.E. Nichols Sulfur-substituted alpha-alkyl phenethylamines as selective and reversible MAO-A inhibitors: biological activities, CoMFA analysis, and active site modeling J. Med. Chem. 48 2005 2407 2419
66. G. La Regina, R. Silvestri, M. Artico, A. Lavecchia, E. Novellino, O. Befani, P. Turini, and E. Agostinelli New pyrrole inhibitors of monoamine oxidase:   synthesis, biological evaluation, and structural determinants of MAO-a and MAO-b selectivity J. Med. Chem. 50 2007 922 931
67. P.C. Waldmeier, A. Delini-Stula, and L. Maitre Preferential deamination of dopamine by an A type monoamine oxidase in rat brain Naunyn Schmiedebergs Arch. Pharmacol. 292 1976 9 14
68. T. Kato, B. Dong, K. Ishii, and H. Kinemuchi Brain dialysis: in vivo metabolism of dopamine and serotonin by monoamine oxidase A but not B in the striatum of unrestrained rats J. Neurochem. 46 1986 1277 1282
69. L. Pisani, G. Muncipinto, T.F. Miscioscia, O. Nicolotti, F. Leonetti, M. Catto, C. Caccia, P. Salvati, R. Soto-Otero, E. Mendez-Alvarez, C. Passeleu, and A. Carotti Discovery of a novel class of potent coumarin monoamine oxidase B inhibitors: development and biopharmacological profiling of 7-[(3-chlorobenzyl) oxy]-4-[(methylamino)methyl]-2H-chromen-2-one methanesulfonate (NW-1772) as a highly potent, selective, reversible, and orally active monoamine oxidase B inhibitor J. Med. Chem. 52 2009 6685 6706
70. C. Binda, J. Wang, L. Pisani, C. Caccia, A. Carotti, P. Salvati, D.E. Edmondson, and A. Mattevi Structures of human monoamine oxidase B complexes with selective noncovalent inhibitors: safinamide and coumarin analogs J. Med. Chem. 50 2007 5848 5852
71. M. Alterman, and A. Hallberg Fast microwave-assisted preparation of aryl and vinyl nitriles and the corresponding tetrazoles from organo-halides J. Org. Chem. 65 2000 7984 7989
72. R. Hunter, Y. Younis, C.I. Muhanji, T.-l. Curtin, K.J. Naidoo, M. Petersen, C.M. Bailey, A. Basavapathruni, and K.S. Anderson C-2-Aryl O-substituted HI-236 derivatives as non-nucleoside HIV-1 reverse-transcriptase inhibitors Bioorg. Med. Chem. 16 2008 10270 10280