Novel (coumarin-3-yl)carbamates as selective MAO-B inhibitors: Synthesis, in vitro and in vivo assays, theoretical evaluation of ADME properties and docking study

European Journal of Medicinal Chemistry

Volumn 63, Issue , 2013, Pages 151-161

  Matos, Maria J ^a   Vilar, Santiago ^a,b   Gonzalez Franco, Rosa M ^a   Uriarte, Eugenio ^a   Santana, Lourdes ^a   Friedman, Carol ^b   Tatonetti, Nicholas P ^b   Viña, Dolores ^c   Fontenla, Jose A ^a  

^a UNIVERSITY OF SANTIAGO DE COMPOSTELA   (Spain)

^b NewYork Presbyterian Hospital   (United States)

^c Universidade de Santiago de Compostela and Instituto de Investigación Sanitaria de Santiago de Compostela   (Spain)

Author keywords

(Coumarin 3 yl)carbamate scaffold; ADME properties; Docking studies; In vitro assays; In vivo assays; Monoamine oxidase (MAO)

Indexed keywords

2 BROMOETHYL(COUMARIN 3 YL)CARBAMATE; AMINE OXIDASE (FLAVIN CONTAINING) ISOENZYME B; BENZYL(COUMARIN 3 YL)CARBAMATE; CARBAMIC ACID; CARBAMIC ACID DERIVATIVE; CLOROMETHYL(COUMARIN 3 YL)CARBAMATE; ETHYL(COUMARIN 3 YL)CARBAMATE; ISOBUTYL(COUMARIN 3 YL)CARBAMATE; ISOPROPYL(COUMARIN 3 YL)CARBAMATE; METHYL(COUMARIN 3 YL)CARBAMATE; MONOAMINE OXIDASE A INHIBITOR; MONOAMINE OXIDASE B INHIBITOR; UNCLASSIFIED DRUG;

ANIMAL EXPERIMENT; ARTICLE; BRAIN CELL; CONTROLLED STUDY; DRUG DOSE INCREASE; DRUG SYNTHESIS; ENZYME INHIBITION; IC 50; IN VITRO STUDY; IN VIVO STUDY; MOLECULAR DOCKING; MOUSE; NONHUMAN;

ANIMALS; BIOCATALYSIS; CARBAMATES; COUMARINS; DOSE-RESPONSE RELATIONSHIP, DRUG; HUMANS; HYDROGEN PEROXIDE; MICE; MODELS, MOLECULAR; MOLECULAR STRUCTURE; MONOAMINE OXIDASE; MONOAMINE OXIDASE INHIBITORS; MOTOR ACTIVITY; PROTEIN BINDING; PROTEIN STRUCTURE, TERTIARY; SELEGILINE; SUBSTRATE SPECIFICITY; TYRAMINE;

EID: 84874527492     PISSN: 02235234     EISSN: 17683254     Source Type: Journal    
DOI: 10.1016/j.ejmech.2013.02.009     Document Type: Article

References (54)

1. Y. Zhu, K. Xiao, L. Ma, B. Xiong, Y. Fu, H. Yu, W. Wang, X. Wang, D. Hu, H. Peng, J. Li, Q. Gong, Q. Chai, X. Tang, H. Zang, J. Li, and J. Shen Bioorg. Med. Chem. 17 2009 1600 1613
2. E. Scarpini, P. Scheltens, and H. Feldman Lancet Neurol. 2 2003 539 547
3. H.W. Querfurth, and F.M. LaFerla N. Engl. J. Med. 362 2010 329 344
4. J. Saura, J.M. Luque, A.M. Cesure, M. Da Prada, V. Chan-Palay, G. Huber, J. Loffler, and J.G. Richard Neuroscience 62 1994 15 30
5. M.B.H. Youdim Exp. Neurobiol. 19 2010 1 14
6. W. Dauer, and S. Przedborski Neuron 39 2003 889 909
7. G.E. Meredith, S. Totterdell, M. Beales, and C.K. Meshul Exp. Neurol. 219 2009 334 340
8. C.W. Olanow, and K.S.P. McNaught Mov. Disord. 21 2006 1806 1823
9. M.D. Yahr, R.C. Duvoisin, M.J. Schear, R.E. Barrett, and M.M. Hoehn Arch. Neurol. 21 1969 343 354
10. A. Carlsson J. Neural Transm. 109 2002 777 787
11. E. Abel Physiol. Behav. 57 1995 611 613
12. G. Engberg, T. Elebring, and H. Nissbrandt J. Pharmacol. Exp. Ther. 259 1991 841 847
13. D.K. Ingram, H.L. Wiener, M.E. Chachich, J.M. Long, J. Hengemihle, and M. Gupta Neurobiol. Aging 14 1993 431 440
14. T. Nagatsu Neurotoxicology 25 2004 11 20
15. P. Dostert, B.M. Strolin, and M. Jalfre Monoamine oxidase: basic and clinical frontiers Exerpta Medica 1982 Elsevier Amsterdam 197 208
16. T.P. Singer F. Muller, Chemistry and Biochemistry of Flavoenzymes vol. 2 1991 CRC Press Boca Raton 437 470
17. K.F. Tipton Cell Biochem. Funct. 4 1986 79 87
18. A.W.J. Bach, N.C. Lan, D.L. Johnson, C.W. Abell, M.E. Bembenek, S.W. Kwan, P.H. Seeburg, and J.C. Shih Proc. Natl. Acad. Sci. U. S. A. 85 1988 4934 4938
19. J. Wouters Curr. Med. Chem. 5 1998 137 162
20. J. Grimsby, N.C. Lan, R. Neve, K. Chen, and J.C. Shih J. Neurochem. 55 1990 1166 1169
21. A.S. Kalgutkar, and N. Castagnoli Jr. Med. Res. Rev. 15 1995 325 388
22. R.M. Geha, I. Rebrin, K. Chen, and J.C. Shih J. Biol.Chem. 276 2001 9877 9882
23. J. Ma, M. Yoshimura, E. Yamashita, A. Nakagawa, A. Ito, and T. Tsukihara J. Mol. Biol. 338 2004 103 114
24. M.V. Rudorfer, and V.Z. Potter Drugs 37 1989 713 738
25. H.H. Fernandez, and J.J. Chen Clin. Neuropharmacol. 30 2007 150 168
26. H. Zheng, M. Fridkin, and M.B.H. Youdim Neurochem. Res. 35 2010 2117 2123
27. M.B. Youdim, A.O. Bar, M. Yogev-Falach, O. Weinreb, W. Maruyama, M. Naoi, and T. Amit J. Neurosci. Res. 79 2005 172 179
28. F. Borges, F. Roleira, N. Milhazes, E. Uriarte, and L. Santana Front. Med. Chem. 4 2009 23 85
29. R. Hoerr, and M. Noeldner CNS Drug Rev. 8 2002 143 158
30. D. Viña, M.J. Matos, M. Yáñez, L. Santana, and E. Uriarte MedChemComm 3 2011 213 218
31. C. Brühlmann, F. Ooms, P.A. Carrupt, B. Testa, M. Catto, F. Leonetti, C. Altomare, and A. Carotti J. Med. Chem. 44 2001 3195 3198
32. M.J. Matos, D. Viña, E. Quezada, C. Picciau, G. Delogu, F. Orallo, L. Santana, and E. Uriarte Bioorg. Med. Chem. Lett. 19 2009 3268 3270
33. M.J. Matos, D. Viña, C. Picciau, F. Orallo, L. Santana, and E. Uriarte Bioorg. Med. Chem. Lett. 19 2009 5053 5055
34. M.J. Matos, D. Viña, P. Janeiro, F. Borges, L. Santana, and E. Uriarte Bioorg. Med. Chem. Lett. 20 2010 5157 5160
35. D. Viña, M.J. Matos, G. Ferino, E. Cadoni, R. Laguna, F. Borges, E. Uriarte, and L. Santana Chem. Med. Chem. 7 2012 464 470
36. M.J. Matos, C. Terán, Y. Pérez-Castillo, E. Uriarte, L. Santana, and D. Viña J. Med. Chem. 54 2011 7127 7137
37. S. Serra, G. Ferino, M.J. Matos, S. Vázquez-Rodríguez, G. Delogu, D. Viña, E. Cadoni, L. Santana, and E. Uriarte Bioorg. Med. Chem. Lett. 22 2012 258 261
38. M.J. Matos, S. Vázquez-Rodríguez, E. Uriarte, L. Santana, and D. Viña Bioorg. Med. Chem. Lett. 21 2011 4224 4227
39. F. Chimenti, D. Secci, A. Bolasco, P. Chimenti, B. Bizzarri, A. Granese, S. Carradori, M. Yáñez, F. Orallo, F. Ostusi, and S. Alcaro J. Med. Chem. 52 2009 1935 1942
40. P. Flaherty, K. Castagnoli, Y.-X. Wang, and N. Castagnoli J. Med. Chem. 39 1996 4756 4761
41. A. Carotti, C. Altomare, M. Catto, C. Gnerre, L. Summo, A. De Marco, S. Rose, P. Jenner, and B. Testa Chem. Biodiversity 3 2006 134 149
42. M. Yáñez, N. Fraiz, E. Cano, and F. Orallo Biochem. Biophys. Res. Commun. 344 2006 688 695
43. C. Binda, J. Wang, L. Pisani, C. Caccia, A. Carotti, P. Salvati, D.E. Edmondson, and A. Mattevi J. Med. Chem. 50 2007 5848 5852
44. RCSB Protein Data Bank: http://www.rcsb.org/ (accessed Jun 2012).
45. Maestro, Version 9.2 2011 Schrödinger, LLC New York, NY
46. QM-polarized Ligand Docking Protocol; Glide Version 5.7, Jaguar Version 7.8, QSite Version 5.7 2011 Schrödinger, LLC New York, NY
47. Prime, Version 3.0 2011 Schrödinger, LLC New York, NY
48. M Cheminformatics, Bratislava, SlovakRepublic, http://www.molinspiration. com/services/properties.html (accessed Jun 2012).
49. C.A. Lipinski, F. Lombardo, B.W. Dominy, and P.J. Feeney Adv. Drug Deliv. Rev. 23 1997 3 26
50. P. Ertl, B. Rohde, and P. Selzer J. Med. Chem. 43 2000 3714 3717
51. M.J. Matos, A. Gaspar, S. Kachler, K.-N. Klotz, F. Borges, L. Santana, and E. Uriarte J. Pharm. Pharmacol. 65 2013 30 34
52. H. Takahashi, H. Takechi, K. Kubo, and T. Matsumoto Heterocycles 72 2007 123 126
53. LigPrep, Version 2.5 2011 Schrödinger, LLC New York, NY
54. Jaguar, Version 7.8 2011 Schrödinger, LLC New York, NY