Synthesis, semipreparative HPLC separation, biological evaluation, and 3D-QSAR of hydrazothiazole derivatives as human monoamine oxidase B inhibitors

Bioorganic and Medicinal Chemistry

Volumn 18, Issue 14, 2010, Pages 5063-5070

  Chimenti, Franco ^a   Secci, Daniela ^a   Bolasco, Adriana ^a   Chimenti, Paola ^a   Granese, Arianna ^a   Carradori, Simone ^a   MacCioni, Elias ^b   Cardia, M Cristina ^b   Yáñez, Matilde ^c   Orallo, Francisco ^c   Alcaro, Stefano ^d   Ortuso, Francesco ^d   Cirilli, Roberto ^e   Ferretti, Rosella ^e   Distinto, Simona ^d,g   Kirchmair, Johannes ^f   Langer, Thierry ^g  

^a SAPIENZA UNIVERSITY OF ROME   (Italy)

^b UNIVERSITY OF CAGLIARI   (Italy)

^c UNIVERSITY OF SANTIAGO DE COMPOSTELA   (Spain)

^d UNIVERSITY MAGNA GRAECIA OF CATANZARO   (Italy)

^e ISTITUTO SUPERIORE DI SANITÀ   (Italy)

^f UNIVERSITY OF INNSBRUCK   (Austria)

^g Inte:Ligand Software Entwicklungs und Consulting GmbH   (Austria)

Author keywords

3D QSAR; Human monoamine oxidase B inhibitors; Hydrazothiazole derivatives

Indexed keywords

AMINE OXIDASE (FLAVIN CONTAINING) ISOENZYME A; AMINE OXIDASE (FLAVIN CONTAINING) ISOENZYME B; HYDRAZONE DERIVATIVE; MONOAMINE OXIDASE B INHIBITOR; POLYCYCLIC AROMATIC HYDROCARBON DERIVATIVE; THIAZOLE DERIVATIVE;

ARTICLE; CHIRALITY; COMPARATIVE MOLECULAR FIELD ANALYSIS; CONCENTRATION RESPONSE; DRUG DESIGN; DRUG POTENCY; DRUG SCREENING; DRUG SELECTIVITY; DRUG SYNTHESIS; ENANTIOSELECTIVITY; ENZYME ACTIVE SITE; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; IN VITRO STUDY; PHARMACOPHORE; QUANTITATIVE STRUCTURE ACTIVITY RELATION; QUANTUM YIELD; STEREOCHEMISTRY;

CHROMATOGRAPHY, HIGH PRESSURE LIQUID; HUMANS; HYDRAZONES; MODELS, MOLECULAR; MONOAMINE OXIDASE; MONOAMINE OXIDASE INHIBITORS; QUANTITATIVE STRUCTURE-ACTIVITY RELATIONSHIP; THIAZOLES;

EID: 77955325332     PISSN: 09680896     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.bmc.2010.05.070     Document Type: Article

References (60)

1. D.E. Edmondson, A. Mattevi, C. Binda, M. Li, and F. Hubálek Curr. Med. Chem. 11 2004 1983
2. D.E. Edmondson, L. De Colibus, C. Binda, M. Li, and A. Mattevi J. Neural Transm. 114 2007 703
3. D.E. Edmondson, C. Binda, J. Wang, A.K. Upadhayay, and A. Mattevi Biochemistry 48 2009 4220
4. J.C. Shih, K. Chen, and M.J. Ridd Annu. Rev. Neurosci. 22 1999 197
5. J.C. Shih, and K. Chen Curr. Med. Chem. 11 2004 1995
6. L.M. Sayre, G. Perry, and M.A. Smith Chem. Res. Toxicol. 21 2008 172
7. F. Blandini CNS Drug Rev. 11 2005 183
8. M.B.H. Youdim, D.E. Edmondson, and K.F. Tipton Nat. Rev. 7 2006 295
9. M. Bortolato, K. Chen, and J.C. Shih Adv. Drug Deliv. Rev. 60 2008 1527
10. P. Riederer, L. Lachenmayer, and G. Laux Curr. Med. Chem. 11 2004 2033
11. M. Da Prada, R. Kettler, H.H. Keller, A.M. Cesura, J.G. Richards, J. Saura Marti, D. Muggli-Maniglio, P.C. Wyss, E. Kyburz, and R. Imhof J. Neural Transm. Suppl. 29 1990 279
12. D.R. Guay Am. J. Geriatr. Pharmacother. 4 2006 330
13. G.D. Mellick, D.D. Buchanan, S.J. McCann, K.M. James, A.G. Johnson, D.R. Davis, N. Liyou, D. Chan, and D.G. Le Couteur Mov. Disord. 14 1999 219
14. B. Drukarch, and F.L. Muiswinkel Biochem. Pharmacol. 59 2000 1023
15. M.C. Carreiras, and J.L. Marco Curr. Pharm. Des. 10 2004 3167
16. S.Y. Son, J. Ma, Y. Kondou, M. Yoshimura, E. Yamashita, and T. Tsukihara Proc. Natl. Acad. Sci. U.S.A. 105 2008 5739 Data deposition: www.pdb.org (PDB ID code 2Z5X)
17. F. Hubálek, C. Binda, A. Khalil, M. Li, A. Mattevi, N. Castagnoli, and D.E. Edmondson J. Biol. Chem. 280 2005 15761 Data deposition: www.pdb.org (PDB ID code 2BK3)
18. M. Li, C. Binda, A. Mattevi, and D.E. Edmondson Biochemistry 45 2006 4775
19. A. Bolasco, R. Fioravanti, and S. Carradori Expert Opin. Ther. Patents 15 2005 1763
20. J. Wouters Curr. Med. Chem. 5 1998 137
21. F. Chimenti, D. Secci, A. Bolasco, P. Chimenti, A. Granese, O. Befani, P. Turini, S. Alcaro, and F. Ortuso Bioorg. Med. Chem. Lett. 14 2004 3697
22. F. Chimenti, D. Secci, A. Bolasco, P. Chimenti, A. Granese, S. Carradori, O. Befani, P. Turini, S. Alcaro, and F. Ortuso Bioorg. Med. Chem. Lett. 16 2006 4135
23. F. Chimenti, D. Secci, A. Bolasco, P. Chimenti, B. Bizzarri, A. Granese, S. Carradori, M. Yáñez, F. Orallo, S. Alcaro, and F. Ortuso J. Med. Chem. 52 2009 1935
24. F. Chimenti, E. Maccioni, D. Secci, A. Bolasco, P. Chimenti, A. Granese, O. Befani, P. Turini, S. Alcaro, F. Ortuso, R. Cirilli, F. La Torre, M.C. Cardia, and S. Distinto J. Med. Chem. 48 2005 7113
25. F. Chimenti, A. Bolasco, F. Manna, D. Secci, P. Chimenti, A. Granese, O. Befani, P. Turini, R. Cirilli, F. La Torre, S. Alcaro, F. Ortuso, and T. Langer Curr. Med. Chem. 13 2006 1411
26. F. Chimenti, S. Carradori, D. Secci, A. Bolasco, B. Bizzarri, P. Chimenti, A. Granese, M. Yáñez, and F. Orallo Eur. J. Med. Chem. 45 2010 800
27. F. Chimenti, E. Maccioni, D. Secci, A. Bolasco, P. Chimenti, A. Granese, O. Befani, P. Turini, S. Alcaro, F. Ortuso, M.C. Cardia, and S. Distinto J. Med. Chem. 50 2007 707
28. F. Chimenti, E. Maccioni, D. Secci, A. Bolasco, P. Chimenti, A. Granese, S. Carradori, S. Alcaro, F. Ortuso, M. Yáñez, F. Orallo, R. Cirilli, R. Ferretti, and F. La Torre J. Med. Chem. 51 2008 4874
29. K.F. Tipton Biochem. J. 128 1972 913
30. A. Dar, K.M. Khan, H.S. Ateeq, S. Khan, S. Rahat, S. Perveen, and C.T. Supuran J. Enzyme Inhib. Med. Chem. 20 2005 269
31. C. Binda, J. Wang, M. Li, F. Hubálek, A. Mattevi, and D.E. Edmondson Biochemistry 47 2008 5616
32. F. Chimenti, S. Carradori, D. Secci, A. Bolasco, P. Chimenti, A. Granese, and B. Bizzarri J. Heterocycl. Chem. 46 2009 575
33. F. Chimenti, D. Secci, A. Bolasco, P. Chimenti, A. Granese, S. Carradori, M. D'Ascenzio, M. Yáñez, and F. Orallo Med. Chem. Commun. 2010 10.1039/c0md00014K
34. G. Raciti, P. Mazzone, A. Raudino, G. Mazzone, and A. Cambria Bioorg. Med. Chem. 3 1995 1485
35. F. Castelli, M.T. Cambria, P. Mazzone, and R. Pignatello Thermochim. Acta 302 1997 143
36. A. Cambria, A. Raudino, A. Geronikaki, G. Buemi, G. Raciti, P. Mazzone, S. Guccione, and S. Ragusa J. Enzyme Inhib. 14 1999 307
37. D.I. Pearson, H.W. Poper, and W.E. Hargrove Org. Synth. 5 1973 117
38. R. Cirilli, R. Ferretti, F. La Torre, D. Secci, A. Bolasco, S. Carradori, and M. Pierini J. Chromatogr., A 1172 2007 160
39. M. Yáñez, N. Fraiz, E. Cano, and F. Orallo Biochem. Biophys. Res. Commun. 344 2006 688
40. K.F. Tipton, S. Boyce, J. O'Sullivan, G.P. Davey, and J. Healy Curr. Med. Chem. 11 2004 1965
41. S.E. Szedlacsek, and R.G. Duggleby Methods Enzymol. 249 1995 144
42. M. Gerlach, P. Riederer, and M.B.H. Youdim Eur. J. Pharmacol. 226 1992 97
43. E.M. O'Brien, K.F. Tipton, M. Meroni, and P. Dostert J. Neural Transm. Suppl. 41 1994 295
44. M. Clark, R.D. Cramer III, D.M. Jones, D.E. Patterson, and P.E. Simeroth Tetrahedron Comput. Methodol. 3 1990 47
45. Sybyl7.2, Tripos, St Louis, Missouri, USA.
46. M. Clark, R.D. Cramer III, and N. Van Opdenbosch J. Comput. Chem. 10 2004 982
47. M.J.D. Powell Math. Prog. 12 1977 241
48. J. Gasteiger, and M. Marsili Tetrahedron 36 1980 3219
49. T. Langer, and R.D. Hoffmann J. Chem. Inf. Comput. Sci. 38 1998 325
50. C.-K. Ryu, Y. Lee, S.-g. Park, H.-J. You, R.-Y. Lee, S.-Y. Lee, and S. Choi Bioorg. Med. Chem. 16 2008 9772
51. S.S. Chaudhaery, K.K. Roy, and A.K. Saxena J. Chem. Inf. Model. 49 2009 1590
52. Catalyst 4.11, Accelrys, San Diego, CA, USA.
53. glide, Schrodinger Inc, Portland, OR.
54. R. Clark J. Comput. Aided Mol. Des. 22 2008 507
55. O. Nicolotti, T.F. Miscioscia, A. Carotti, F. Leonetti, and A. Carotti J. Chem. Inf. Model. 48 2008 1211
56. Macromodel' Schrodinger Inc, Portland, OR.
57. L. De Colibus, M. Li, C. Binda, A. Lustig, E.D. Edmondson, and A. Mattevi Proc. Natl. Acad. Sci. U.S.A. 102 2005 12684 Data deposition: www.pdb.org (PDB ID code 2BXR, 2BXS, and 2BYB)
58. C. Binda, P. Newton-Vinson, F. Hubálek, D.E. Edmondson, and A. Mattevi Nat. Struct. Biol. 9 2002 22 Data deposition: www.pdb.org (PDB ID code 1GOS)
59. A.M. Gamper, R.H. Winger, K.R. Liedl, C.A. Sotriffer, J.M. Varga, R.T. Kroemer, and B.M. Rode J. Med. Chem. 39 1996 3882
60. R.D. Cramer, J.D. Bunce, D.E. Patterson, and I.E. Frank Quant. Struct.-Act. Relat. 7 1988 18