Synthesis and study of a series of 3-arylcoumarins as potent and selective monoamine oxidase B inhibitors

Journal of Medicinal Chemistry

Volumn 54, Issue 20, 2011, Pages 7127-7137

  Matos, Maria J ^a   Terán, Carmen ^b   Pérez Castillo, Yunierkis ^b   Uriarte, Eugenio ^a   Santana, Lourdes ^a   Viña, Dolores ^a  

^a UNIVERSITY OF SANTIAGO DE COMPOSTELA   (Spain)

^b UNIVERSITY OF VIGO   (Spain)

Author keywords

[No Author keywords available]

Indexed keywords

3 (2 HYDROXYPHENYL) 6 METHYLCOUMARIN; 3 (3 BROMO 3 METHOXYPHENYL) 6 METHYLCOUMARIN; 3 (3 BROMO 3,4,5 TRIMETHOXYPHENYL) 6 METHYLCOUMARIN; 3 (3 BROMO 3,5 DIMETHOXYPHENYL) 6 METHYLCOUMARIN; 3 (3 BROMO 4 METHOXYPHENYL) 6 METHYLCOUMARIN; 3 (3 HYDROXYPHENYL) 6 METHYLCOUMARIN; 3 (4 METHYLPHENYL) 6 (2 OXOPROPOXY)COUMARIN; 6 HYDROXY 3 (4 METHYLPHENYL)COUMARIN; 6 METHOXY 3 (3 METHYLPHENYL)COUMARIN; 6 METHOXY 3 (4 METHYLPHENYL)COUMARIN; 6 METHYL 3 (3 METHYLPHENYL)COUMARIN; 6 METHYL 3 (4 METHYLPHENYL)COUMARIN; 6 METHYL 3 [3 (2 OXOPROPOXY)PHENYL]COUMARIN; AMINE OXIDASE (FLAVIN CONTAINING) ISOENZYME A; AMINE OXIDASE (FLAVIN CONTAINING) ISOENZYME B; COUMARIN DERIVATIVE; IPRONIAZID; SELEGILINE; UNCLASSIFIED DRUG;

ARTICLE; DRUG POTENCY; DRUG STRUCTURE; DRUG SYNTHESIS; IC 50; MOLECULAR INTERACTION; SUBSTITUTION REACTION;

COUMARINS; CRYSTALLOGRAPHY, X-RAY; HUMANS; ISOENZYMES; MODELS, MOLECULAR; MOLECULAR STRUCTURE; MONOAMINE OXIDASE; MONOAMINE OXIDASE INHIBITORS; RECOMBINANT PROTEINS; STRUCTURE-ACTIVITY RELATIONSHIP;

EID: 80054908624     PISSN: 00222623     EISSN: 15204804     Source Type: Journal    
DOI: 10.1021/jm200716y     Document Type: Article

References (67)

1. Murray, R. D. H., Mendez, J., and Brown, S. A. The natural coumarins occurrence. In Chemistry and Biochemistry; John Wiley and Sons: Chichester, UK, 1982.
2. Murray, R. D. H. Naturally occurring plant coumarins Prog. Chem. Org. Nat. Prod. 2002, 83, 1-673
3. Borges, F.; Roleira, F.; Milhazes, N.; Santana, L.; Uriarte, E. Simple coumarins and analogues in medicinal chemistry: occurrence, synthesis and biological activity Curr. Med. Chem. 2005, 12, 887-916 (Pubitemid 40443846)
4. Borges, F.; Roleira, F.; Milhazes, N.; Uriarte, E.; Santana, L. Simple Coumarins: Privileged Scaffolds in Medicinal Chemistry Front. Med. Chem. 2009, 4, 23-85
5. ÓKennedy, R. Coumarins. Biology, Applications and Mode of Action; Thornes, R. D., Ed.; John Wiley and Sons: New York, 1997.
6. Belluti, F.; Fontana, G.; Bo, L.; Carenini, N.; Giommarelli, C.; Zunino, F. Design, synthesis and anticancer activities of stilbene-coumarin hybrid compounds: identification of novel proapoptotic agents Bioorg. Med. Chem. 2010, 18, 3543-3550
7. Riveiro, M. E.; Moglioni, A.; Vazquez, R.; Gomez, N.; Facorro, G.; Piehl, L.; de Celis, E. R.; Shayo, C.; Davio, C. Structural insights into hydroxycoumarin-induced apoptosis in U-937 cells Bioorg. Med. Chem. 2008, 16, 2665-2675 (Pubitemid 351380918)
8. Fylaktakidou, K. C.; Hadjipavlou-Litina, D. J.; Litinas, K. E.; Nicolaides, D. N. Natural and synthetic coumarin derivatives with anti-inflammatory/antioxidant activities Curr. Pharm. Des. 2004, 10, 3813-3833 (Pubitemid 39409872)
9. Roussaki, M.; Kontogiorgis, C.; Hadjipavlou-Litina, D. J.; Hamilakis, S. A novel synthesis of 3-aryl coumarins and evaluation of their antioxidant and lipoxygenase inhibitory activity Bioorg. Med. Chem. Lett. 2010, 20, 3889-3892
10. Vilar, S.; Quezada, E.; Santana, L.; Uriarte, E.; Yanez, M.; Fraiz, N.; Alcaide, C.; Cano, E.; Orallo, F. Design, synthesis, and vasorelaxant and platelet antiaggregatory activities of coumarin-resveratrol hybrids Bioorg. Med. Chem. Lett. 2006, 16, 257-261 (Pubitemid 41680608)
11. Ostrov, D. A.; Hernández Prada, J. A.; Corsino, P. E.; Finton, K. A.; Le, N.; Rowe, T. C. Discovery of novel DNA gyrase inhibitors by high-throughput virtual screening Antimicrob. Agents Chemother. 2007, 51, 3688-3698 (Pubitemid 47519360)
12. Chimenti, F.; Bizzarri, B.; Bolasco, A.; Secci, D.; Chimenti, P.; Granese, A.; Carradori, S.; Rivanera, D.; Zicari, A.; Scaltrito, M. M.; Sisto, F. Synthesis, selective anti- Helicobacter pylori activity, and cytotoxicity of novel N -substituted-2-oxo-2 H -1-benzopyran-3-carboxamides Bioorg. Med. Chem. Lett. 2010, 20, 4922-4926
13. Neyts, J.; De Clercq, E.; Singha, R.; Chang, Y. H.; Das, A. R.; Chakraborty, S. K.; Hong, S. C.; Tsay, S.-C.; Hsu, M.-H.; Hwu, J. R. Structure-activity relationship of new anti-hepatitis C virus agents: heterobicycle-coumarin conjugates J. Med. Chem. 2009, 52, 1486-1490
14. Kostova, I. Coumarins as inhibitors of HIV reverse transcriptase Curr. HIV Res. 2006, 4, 347-363 (Pubitemid 44054830)
15. Chilin, A.; Battistutta, R.; Bortolato, A.; Cozza, G.; Zanatta, S.; Poletto, G.; Mazzorana, M.; Zagotto, G.; Uriarte, E.; Guiotto, A.; Meggio, F.; Moro, S. Coumarin as attractive casein kinase 2 (CK2) inhibitor scaffold: an integrate approach to elucidate the putative binding motif and explain structure-activity relationships J. Med. Chem. 2008, 51, 752-759 (Pubitemid 351304684)
16. Zhou, X.; Wang, X. B.; Wang, T.; Kong, L. Yi. Design, synthesis, and acetylcholinesterase inhibitory activity of novel coumarin analogues Bioorg. Med. Chem. 2008, 16, 8011-8021
17. Garino, C.; Tomita, T.; Pietrancosta, N.; Laras, Y.; Rosas, R. Naphthyl and coumarinyl biarylpiperazine derivatives as highly potent human β-secretase inhibitors. Design, synthesis, and enzymatic BACE-1 and cell assays J. Med. Chem. 2006, 49, 4275-4285 (Pubitemid 44036671)
18. Chimenti, F.; Secci, D.; Bolasco, A.; Chimenti, P.; Bizzarri, B.; Granese, A.; Carradori, S.; Yanez, M.; Orallo, F.; Ortuso, F.; Alcaro, S. Synthesis, molecular modeling, and selective inhibitory activity against human monoamine oxidases of 3-carboxamido-7-substituted coumarins J. Med. Chem. 2009, 52, 1935-1942
19. Pisani, L.; Muncipinto, G.; Miscioscia, T. F.; Nicolotti, O.; Leonetti, F.; Catto, M.; Caccia, C.; Salvati, P.; Soto-Otero, R.; Mendez-Alvarez, E.; Passeleu, C.; Carotti, A. Discovery of a novel class of potent coumarin monoamine oxidase B inhibitors: development and biopharmacological profiling of 7-[(3-chlorobenzyl)oxy]-4-[(methylamino)methyl]-2 H -chromen-2-one methanesulfonate (NW-1772) as a highly potent, selective, reversible, and orally active monoamine oxidase B inhibitor J. Med. Chem. 2009, 52, 6685-6706
20. Gnerre, C.; Catto, M.; Francesco, L.; Weber, P.; Carrupt, P.-A.; Altomare, C.; Carotti, A.; Testa, B. Inhibition of monoamine oxidase by functionalized coumarin derivatives: biological activities, QSAR, and 3D-QSARs J. Med. Chem. 2000, 43, 4747-4758 (Pubitemid 32002686)
21. Tipton, K. F. Enzymology of monoamine oxidase Cell. Biochem. Funct. 1986, 4, 79-87 (Pubitemid 16140104)
22. Dostert, P.; Strolin, B. M.; Jafre, M. Monoamine oxidase: basic and clinical frontiers. In Excerpta Medica; Elsevier: Amsterdam, 1982; pp 197.
23. Singer, T. P. In Chemistry and Biochemistry of Flavoenzymes; Muller, F., Ed.; CRC Press: Boca Raton FL, 1991; Vol. 2, pp 437.
24. Bach, A. W. J.; 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
25. Wouters, J. Structural aspects of monoamine oxidase and its reversible inhibition Curr. Med. Chem. 1998, 5, 137-162 (Pubitemid 28183854)
26. Grimsby, J.; Lan, N. C.; Neve, R.; Chen, K.; Shih, J. C. Tissue distribution of human monoamine oxidase A and B mRNA J. Neurochem. 1990, 55, 1166-1169
27. Kalgutkar, A. S.; Castagnoli, N., Jr.; Testa, B. Selective inhibitors of monoamine oxidase (MAO-A and MAO-B) as probes of its catalytic site and mechanism Med. Res. Rev. 1995, 15, 325-388
28. Geha, R. M.; Rebrin, I.; Chen, K.; Shih, J. C. Substrate and inhibitor specificities for human monoamine oxidase A and B are influenced by a single amino acid J. Biol. Chem. 2001, 276, 9877-9882
29. 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, 103-115
30. Weyler, W.; Hsu, Y. P. P.; Breakefield, X. O. Biochemistry and genetics of monoamine oxidase Pharmacol. Ther. 1990, 47, 391-417 (Pubitemid 20309559)
31. Rudorfer, M. V.; Potter, V. Z. Antidepressants. A comparative review of the clinical pharmacology and therapeutic use of the "newer" versus the "older" drugs Drugs 1989, 37, 713-738 (Pubitemid 19138618)
32. Gerlach, M.; Double, K.; Reichmann, H.; Riederer, P. Arguments for the use of dopamine receptor agonists in clinical and preclinical Parkinsońs diseases J. Neural Transm. Suppl. 2003, 167-193
33. Fernandez, H. H.; Chen, J. J. Monamine oxidase inhibitors: current and emerging agents for Parkinson disease Clin. Neuropharmacol. 2007, 30, 150-168 (Pubitemid 46871865)
34. Riederer, P.; Danielczyk, W.; Grunblatt, E. Monoamine oxidase-B inhibition in Alzheimer's disease Neurotoxicology 2004, 25, 271-277 (Pubitemid 38044188)
35. Binda, C.; Newton-Vinson, P.; Hubalek, F.; Edmondson, D. E.; Mattevi, A. Structure of human monoamine oxidase B, a drug target for the treatment of neurological disorders Nature Struct. Mol. Biol. 2002, 9, 22-26 (Pubitemid 34049174)
36. Binda, C.; Li, M.; Hubálek, F.; Restelli, N.; Edmondson, D. E.; Mattevi, A. Insights into the mode of inhibition of human mitochondrial monoamine oxidase B from high-resolution crystal structures Proc. Natl. Acad. Sci. U.S.A. 2003, 100, 9750-9755 (Pubitemid 37087013)
37. 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 (Pubitemid 41279426)
38. Binda, C.; Hubalek, F.; Li, M.; Herzig, Y.; Sterling, J.; Edmondson, D. E.; Mattevi, A. Crystal structures of monoamine oxidase B in complex with four inhibitors of the N -propargylaminoindane class J. Med. Chem. 2004, 47, 1767-1774 (Pubitemid 38380920)
39. Milczek, E. M.; Bonivento, D.; Binda, C.; Mattevi, A.; McDonald, I. A.; Edmondson, D. E. Structural and mechanistic studies of mofegiline inhibition of recombinant human monoamine oxidase B J. Med. Chem. 2008, 51, 8019-8026
40. Sayre, L. M.; Perry, G.; Smith, M. A. Oxidative stress and neurotoxicity Chem. Res. Toxicol. 2008, 21, 172-188 (Pubitemid 351219718)
41. Yamada, M.; Yasuhara, H. Clinical pharmacology of MAO inhibitors: safety and future Neurotoxicology 2004, 25, 11-20
42. Filip, V.; Kolibas, E. Selegiline in the treatment of Alzheimer's disease: a long-term randomized placebo-controlled trial. Czech and Slovak senile dementia of Alzheimer type study group J. Psychiatr. Neurosci. 1999, 24, 234-243
43. Annan, N.; Silverman, R. B. New analogs of N -(2-aminoethyl)-4- chlorobenzamide (Ro 16-6491). Some of the most potent monoamine oxidase-B inactivators J. Med. Chem. 1993, 36, 3968-3970 (Pubitemid 24006727)
44. Harfenist, M.; Joyner, C.; Mize, P.; White, H. Selective inhibitors of monoamine oxidase. 2. Arylamide SAR J. Med. Chem. 1994, 37, 2085-2089 (Pubitemid 24233621)
45. Chimenti, F.; Secci, D.; Bolasco, A.; Chimenti, P.; Granese, A.; Carradori, S.; Yanez, M.; Orallo, F.; Sanna, M. L.; Gallinella, B.; Cirilli, R. Synthesis, stereochemical separation, and biological evaluation of selective inhibitors of human MAO-B: 1-(4-arylthiazol-2-yl)-2-(3-methylcyclohexylidene) hydrazines J. Med. Chem. 2010, 53, 6516-6520
46. Chimenti, F.; Maccioni, E.; Secci, D.; Bolasco, A.; Chimenti, P.; Granese, A.; Carradori, S.; Alcaro, S.; Ortuso, F.; Yanez, M.; Orallo, F.; Cirilli, R.; Ferretti, R.; La Torre, F. Synthesis, stereochemical identification, and selective inhibitory activity against human monoamine oxidase-B of 2-methylcyclohexylidene-(4-arylthiazol-2-yl)hydrazones J. Med. Chem. 2008, 51, 4874-4880
47. Frederick, R.; Dumont, W.; Ooms, F.; Aschenbach, L.; Van der Schyf, C. J.; Castagnoli, N.; Wouters, J.; Krief, A. Synthesis, structural reassignment, and biological activity of type B MAO inhibitors based on the 5 H -indeno[1,2- c ]pyridazin-5-one core J. Med. Chem. 2006, 49, 3743-3747 (Pubitemid 43902479)
48. Carotti, A.; Catto, M.; Leonetti, F.; Campagna, F.; Soto-Otero, R.; Mendez-Alvarez, E.; Thull, U.; Testa, B.; Altomare, C. Synthesis and monoamine oxidase inhibitory activity of new pyridazine-, pyrimidine-, and 1,2,4-triazine-containing tricyclic derivatives J. Med. Chem. 2007, 50, 5364-5371 (Pubitemid 350057848)
49. Leonetti, F.; Capaldi, C.; Pisani, L.; Nicolotti, O.; Muncipinto, G.; Stefanachi, A.; Cellamare, S.; Caccia, C.; Carotti, A. Solid-phase synthesis and insights into structure-activity relationships of safinamide analogues as potent and selective inhibitors of type B monoamine oxidase J. Med. Chem. 2007, 50, 4909-4916 (Pubitemid 47525474)
50. Rendenbach, B.; Weifenbach, H.; Teschendorf, H. J. Preparation of 7-(arylalkoxy)coumarins as central nervous system agents. (BASF AG). Patent DE 3834861 A1, 1990,.
51. Carotti, A.; Altomare, C.; Catto, M.; Gnerre, C.; Summo, L.; De Marco, A.; Rose, S.; Jenner, P.; Testa, B. Lipophilicity plays a major role in modulating the inhibition of monoamine oxidase B by 7-substituted coumarins Chem. Biodiversity 2006, 3, 134-149 (Pubitemid 43322991)
52. Santana, L.; Uriarte, E.; González-Díaz, H.; Zagotto, G.; Soto-Otero, R.; E. Méndez-Álvarez, E. A QSAR model for in silico screening of MAO-A inhibitors. Prediction, synthesis, and biological assay of novel coumarins J. Med. Chem. 2006, 49, 1149-1156 (Pubitemid 43221661)
53. Santana, L.; González-Díaz, H.; Quezada, E.; Uriarte, E.; Yáñez, M.; Viña, D.; Orallo, F. Quantitative structure-activity relationship and complex network approach to monoamine oxidase A and B inhibitors J. Med. Chem. 2008, 51, 6740-6751
54. Matos, M. J.; Viña, D.; Quezada, E.; Picciau, C.; Delogu, G.; Orallo, F.; Santana, L.; Uriarte, E. A new series of 3-phenylcoumarins as potent and selective MAO-B inhibitors Bioorg. Med. Chem. Lett. 2009, 19, 3268-3270
55. Matos, M. J.; Viña, D.; Picciau, C.; Orallo, F.; Santana, L.; Uriarte, E. Synthesis and evaluation of 6-methyl-3-phenylcoumarins as potent and selective MAO-B inhibitors Bioorg. Med. Chem. Lett. 2009, 19, 5053-5055
56. Matos, M. J.; Viña, D.; Janeiro, P.; Borges, F.; Santana, L.; Uriarte, E. New halogenated 3-phenylcoumarins as potent and selective MAO-B inhibitors Bioorg. Med. Chem. Lett. 2010, 20, 5157-5160
57. Hubálek, F.; Binda, C.; Khalil, A.; Li, M.; Mattevi, A.; Castaganoli, N.; Edmondson, D. E. Demonstration of isoleucine 199 as a structural determinant for the selective inhibition of human monoamine oxidase B by specific reversible inhibitors J. Biol. Chem. 2005, 280, 16761-15766
58. Son, S.-Y.; Ma, J.; Kondou, Y.; Yoshimura, M.; Yamashita, E.; Tsukihara, T. Stucture of human monoamine oxidase A at 2.2 Ø resolution: the control of opening the entry for substrates/inhibitors Proc. Natl. Acad. Sci. U.S.A. 2008, 105, 5739-5744 (Pubitemid 351758442)
59. Binda, C.; Wang, J.; Pisani, L.; Caccia, C.; Carotti, A.; Salvati, P.; Edmondson, D. E.; Mattevi, A. Structures of human monoamine oxidase B complexes with selective noncovalent inhibitors: safinamide and coumarin analogs J. Med. Chem. 2007, 50, 5848-5852 (Pubitemid 350106038)
60. Yáñez, M.; Fraiz, N.; Cano, E.; Orallo, F. Inhibitory effects of cis and trans -resveratrol on noradrenaline and 5-hydroxytryptamine uptake and on monoamine oxidase activity Biochem. Biophys. Res. Commun. 2006, 344, 688-695
61. Lang, P. T.; Brozell, S. R.; Mukherjee, S.; Pettersen, E. F.; Meng, E. C.; Thomas, V.; Rizzo, R. C.; Case, D. A.; James, T. L.; Kuntz, I. D. DOCK 6: combining techniques to model RNA-small molecule complexes RNA 2009, 15, 1219-30
62. Onufriev, A.; Bashford, D.; Case, D. A. Exploring protein native states and large-scale conformational changes with a modified generalized Born model Proteins 2004, 55, 383-394 (Pubitemid 38437495)
63. Graves, A. P.; Shivakumar, D. M.; Boyce, S. E.; Jacobson, M. P.; Case, D. A.; Shoichet, B. K. Rescoring Docking Hit Lists for Model Cavity Sites: Predictions and Experimental Testing J. Mol. Biol. 2008, 377, 914-934
64. Pettersen, E. F.; Goddard, T. D.; Huang, C. C.; Couch, G. S.; Greenblatt, D. M.; Meng, E. C.; Ferrin, T. E. UCSF Chimera-a visualization system for exploratory research and analysis J. Comput. Chem. 2004, 25, 1605-1612
65. Schmidt, M. W.; Baldridge, K. K.; Boatz, J. A.; Elbert, S. T.; Gordon, M. S.; Jensen, J. H.; Koseki, S.; Matsunaga, N.; Nguyen, K. A.; Su, S.; Windus, T. L.; Dupuis, M.; Montgomery, J. A. General atomic and molecular electronic structure system J. Comput. Chem. 1993, 14, 1347-1363
66. OMEGA 2.3.2; OpenEye Scientific Software, Inc.: Santa Fe, NM, 2008; www.eyesopen.com.
67. QUACPAC, version 1.3.1; OpenEye Scientific Software, Inc.: Santa Fe, NM, 2008; www.eyesopen.com.