Design, synthesis and biological evaluation of 5-hydroxy, 5-substituted-pyrimidine-2,4,6-triones as potent inhibitors of gelatinases MMP-2 and MMP-9

European Journal of Medicinal Chemistry

Volumn 58, Issue , 2012, Pages 368-376

  Nicolotti, Orazio ^a   Catto, Marco ^a   Giangreco, Ilenia ^a   Barletta, Maria ^a   Leonetti, Francesco ^a   Stefanachi, Angela ^a   Pisani, Leonardo ^a   Cellamare, Saverio ^a   Tortorella, Paolo ^a   Loiodice, Fulvio ^a   Carotti, Angelo ^a  

^a UNIVERSITY OF BARI   (Italy)

Author keywords

Gelatinases; MMP; Molecular docking; QSAR; ZBG

Indexed keywords

5 [ 1 (BIPHEN 4 YL) 2 OXOPROPYL] 5 HYDROXYHEXAHYDROPYRIMIDINE 2,4,6 TRIONE; 5 [ 2 ( 3' NITROBIPHEN 4 YL) 2 OXOETHYL] 5 HYDROXYHEXAHYDROPYRIMIDINE 2,4,6 TRIONE; 5 [ 2 ( 4' ( N,N DIMETHYLAMINOCARBONYL)BIPHEN 4 YL) 2 OXOETHYL] 5 HYDROXYHEXAHYDROPYRIMIDINE 2,4,6 TRIONE; 5 [ 2 ( 4' (METHYLSULFONYL)BIPHEN 4 YL) 2 OXOETHYL] 5 HYDROXYHEXAHYDROPYRIMIDINE 2,4,6 TRIONE; 5 [ 2 ( 4' (METHYLTHIO)BIPHEN 4 YL) 2 OXOETHYL] 5 HYDROXYHEXAHYDROPYRIMIDINE 2,4,6 TRIONE; 5 [ 2 ( 4' (THIEN 3 YL)PHENYL) 2 OXOETHYL] 5 HYDROXYHEXAHYDROPYRIMIDINE 2,4,6 TRIONE; 5 [ 2 ( 4' (TRIFLUOROMETHOXY)BIPHEN 4 YL) 2 OXOETHYL] 5 HYDROXYHEXAHYDROPYRIMIDINE 2,4,6 TRIONE; 5 [ 2 ( 4' ACETYLBIPHEN 4 YL) 2 OXOETHYL] 5 HYDROXYHEXAHYDROPYRIMIDINE 2,4,6 TRIONE; 5 [ 2 ( 4' CHLOROBIPHEN 4 YL) 2 OXOETHYL] 5 HYDROXYHEXAHYDROPYRIMIDINE 2,4,6 TRIONE; 5 [ 2 ( 4' HYDROXYMETHYL)BIPHEN 4 YL) 2 OXOETHYL] 5 HYDROXYHEXAHYDROPYRIMIDINE 2,4,6 TRIONE; 5 [ 2 ( 4' METHOXYBIPHEN 4 YL) 2 OXOETHYL] 5 HYDROXYHEXAHYDROPYRIMIDINE 2,4,6 TRIONE; 5 [ 2 ( 4' METHYLBIPHEN 4 YL) 2 OXOETHYL] 5 HYDROXYHEXAHYDROPYRIMIDINE 2,4,6 TRIONE; 5 [ 3 (BIPHEN 4 YL) 2 OXOPROPYL] 5 HYDROXYHEXAHYDROPYRIMIDINE 2,4,6 TRIONE; ACETANILIDE; ALKENE DERIVATIVE; ALLOXAN; BIPHENYL DERIVATIVE; GELATINASE A; GELATINASE B; HYDROXYL GROUP; KETOMETHYLENE; MATRIX METALLOPROTEINASE INHIBITOR; NEUTROPHIL COLLAGENASE; PYRIMIDINE DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CONTROLLED STUDY; CROSS LINKING; DRUG BIOAVAILABILITY; DRUG DESIGN; DRUG POTENCY; DRUG SOLUBILITY; DRUG SYNTHESIS; DRUG TARGETING; ENZYME ACTIVE SITE; ENZYME ACTIVITY; ENZYME INHIBITION; HUMAN; IC 50; MOLECULAR DOCKING; MOLECULAR INTERACTION; PHARMACOLOGICAL PARAMETERS; QUANTITATIVE STRUCTURE ACTIVITY RELATION; SUBSTITUTION REACTION;

BARBITURATES; CRYSTALLOGRAPHY, X-RAY; DOSE-RESPONSE RELATIONSHIP, DRUG; DRUG DESIGN; ENZYME INHIBITORS; HUMANS; MATRIX METALLOPROTEINASE 2; MATRIX METALLOPROTEINASE 9; MODELS, MOLECULAR; MOLECULAR STRUCTURE; SERUM ALBUMIN; STRUCTURE-ACTIVITY RELATIONSHIP;

EID: 84868533847     PISSN: 02235234     EISSN: 17683254     Source Type: Journal    
DOI: 10.1016/j.ejmech.2012.09.036     Document Type: Article

References (47)

1. C.J. Malemud Front. Biosci. 11 2006 1696 1701
2. C.M. Overall, and O. Kleifeld Nat. Rev. Cancer 6 2006 227 239
3. J.E. Rundhaug J. Cell. Mol. Med. 9 2005 267 285
4. E.I. Deryugina, and J.P. Quigley Cancer Metastasis Rev. 25 2006 9 34
5. J.H. Hu, P.E. Van den Steen, Q.A. Sang, and G. Opdenakker Nat. Rev. Drug Discov. 6 2007 480 498
6. G. Dormán, S. Cseh, I. Hajdú, L. Barna, D. Kónya, K. Kupai, L. Kovács, and P. Ferdinandy Drugs 70 2010 949 964
7. A.K. Nalla, B. Gorantla, C.S. Gondi, S.S. Lakka, and J.S. Rao Cancer Gene Ther. 17 2010 599 613
8. B. Govinda Rao Curr. Pharm. Des. 11 2005 295 322
9. E. Breuer, J. Frant, and R. Reich Expert Opin. Ther. Patent 15 2005 253 269
10. M.T. Rubino, M. Agamennone, C. Campestre, P. Campiglia, V. Cremasco, R. Faccio, A. Laghezza, F. Loiodice, D. Maggi, E. Panza, A. Rossello, and P. Tortorella ChemMedChem 6 2011 1258 1268
11. M.T. Rubino, M. Agamennone, C. Campestre, G. Fracchiolla, A. Laghezza, F. Loiodice, E. Nuti, A. Rossello, and P. Tortorella ChemMedChem 4 2009 352 362
12. A.R. Folgueras, A. Fueyo, O. Garcia-Suarez, J. Cox, A. Astudillo, P. Tortorella, C. Campestre, A. Gutierrez-Fernandez, M. Fanjul-Fernandez, C.J. Pennington, D.R. Edwards, C.M. Overall, and C. Lopez-Otin J. Biol. Chem. 283 2008 9465 9474
13. M.T. Rubino, D. Maggi, A. Laghezza, F. Loiodice, and P. Tortorella Arch. Pharm. 344 2011 557 563
14. J.A. Blagg, M.C. Noe, L.A. Wolf-Gouveia, L.A. Reiter, E.R. Laird, S.P. Chang, D.E. Danley, J.T. Downs, N.C. Elliott, J.D. Eskra, R.J. Griffiths, J.R. Hardink, A.I. Haugeto, C.S. Jones, J.L. Liras, L.L. Lopresti-Morrow, P.G. Mitchell, J. Pandit, R.P. Robinson, C. Subramanyam, M.L. Vaughn-Bowser, and S.A. Yocum Bioorg. Med. Chem. Lett. 15 2005 1807 1810
15. L.H. Foley, R. Palermo, P. Dunten, and P. Wang Bioorg. Med. Chem. Lett. 11 2001 969 972
16. J. Wang, C. Medina, M.W. Radomski, and J.F. Gilmer Bioorg. Med. Chem. 19 2011 4985 4999
17. L.A. Reiter, K.D. Freeman-Cook, C.S. Jones, G.J. Martinelli, A.S. Antipas, M.A. Berliner, K. Datta, J.T. Downs, J.D. Eskra, M.D. Forman, E.M. Greer, R. Guzman, J.R. Hardink, F. Janat, N.F. Keene, E.R. Laird, J.L. Liras, L.L. Lopresti-Morrow, P.G. Mitchell, J. Pandit, D. Robertson, D. Sperger, M.L. Vaughn-Bowser, D.M. Wallera, and S.A. Yocum Bioorg. Med. Chem. Lett. 16 2006 5822 5826
18. D. Schrigten, H.J. Breyholz, S. Wagner, S. Hermann, O. Schober, M. Schäfers, G. Haufe, and K. Kopka J. Med. Chem. 55 2012 223 232
19. H.J. Breyholz, M. Schäfers, S. Wagner, C. Höltke, A. Faust, H. Rabeneck, B. Levkau, O. Schober, and K. Kopka J. Med. Chem. 48 2005 3400 3409
20. M. Piette, B. Evrard, F. Frankenne, P. Chiap, P. Bertholet, D. Castagne, J.-M. Foidart, L. Delattre, and G. Piel Eur. J. Pharm. Sci. 28 2006 189 195
21. I. Giangreco, G. Lattanzi, O. Nicolotti, M. Catto, A. Laghezza, F. Leonetti, A. Stefanachi, and A. Carotti PLoS One 6 2011 e25597
22. Y. Yan, M.T. Miller, Y. Cao, and S.M. Cohen Bioorg. Med. Chem. Lett. 19 2009 1970 1976
23. B. Flachner, Z. Lörincz, A. Carotti, O. Nicolotti, P. Kuchipudi, N. Remez, F. Sanz, J. Tóvári, M.J. Szabó, B. Bertók, S. Cseh, J. Mestres, and G. Dormán PLoS One 7 2012 e35582
24. C. Altomare, S. Cellamare, L. Summo, M. Catto, A. Carotti, U. Thull, P.-A. Carrupt, B. Testa, and H. Stoeckli-Evans J. Med. Chem. 41 1998 3812 3820
25. C. Hansch, and A. Leo Exploring QSAR - Fundamentals and Applications in Chemistry and Biology - ACS Professional Reference Book 1995 American Chemical Society Washington, DC
26. L. Verdonk, J.C. Cole, M.J. Hartshorn, C.W. Murray, and R.D. Taylor Proteins 52 2003 609 623
27. C. Knox, V. Law, T. Jewison, P. Liu, S. Ly, A. Frolkis, A. Pon, K. Banco, C. Mak, V. Neveu, Y. Djoumbou, R. Eisner, A.C. Guo, and D.S. Wishart Nucl. Acids Res. 39 2011 1035 1041
28. C. Hansch, and T.E. Klein Methods Enzymol. 202 1991 512 543
29. A. Carotti, C. Raguseo, T.E. Klein, R. Langridge, and C. Hansch Chem. Biol. Interact. 67 1988 171 184
30. A. Carotti, C. Raguseo, F. Campagna, R. Langridge, and T.E. Klein Quant. Struct.-Act. Relat. 8 1989 1 10
31. A. Carotti, C. Raguseo, and C. Hansch Quant. Struct.-Act. Relat. 4 1985 145 149
32. A. Carotti, R.N. Smith, S. Wong, C. Hansch, J.M. Blaney, and R. Langridge Arch. Biochem. Biophys. 229 1984 112 125
33. A. Carotti, M.M. Mueller, J.M. Blaney, and R. Langridge J. Med. Chem. 27 1984 1401 1405
34. O. Nicolotti, and A. Carotti J. Chem. Inf. Model. 46 2006 264 276
35. L. Devel, B. Czarny, F. Beau, D. Georgiadis, E. Stura, and V. Dive Biochimie 92 2010 1501 1508
36. J. Grimm, B.J. Hubs, L.T. Miller, K. Otte, M.P. Siliphaivanh, M. Stanton, G.K. Wilson, D. Witter, H. Zhou, (Merck & Co.), Patent WO2007100657, 2007.
37. K.J. Wilson, D.J. Witter, J.B. Grimm, P. Siliphaivanh, K.M. Otte, A.M. Kral, J.C. Fleming, A. Harsch, J.E. Hamill, J.C. Cruz, M. Chenard, A.A. Szewczak, R.E. Middleton, B.L. Hughes, W.K. Dahlberg, J.P. Secrist, and T.A. Miller Bioorg. Med. Chem. Lett. 18 2008 1859 1863
38. O. Nicolotti, I. Giangreco, T.F. Miscioscia, and A. Carotti J. Chem. Inf. Model. 49 2009 2290 2302
39. O. Nicolotti, T.F. Miscioscia, A. Carotti, F. Leonetti, and A. Carotti J. Chem. Inf. Model. 48 2008 1211 1226
40. A. Tochowicz, K. Maskos, R. Huber, R. Oltenfreiter, V.R. Dive, A. Yiotakis, M. Zanda, W. Bode1, and P. Goettig J. Mol. Biol. 371 2007 989 1006
41. H. Brandstetter, F. Grams, D. Glitz, D. Lang, R. Huber, W. Bode, H.W. Krell, and R.A. Engh J. Biol. Chem. 276 2001 17405 17412
42. P. Pospisil, P. Ballmer, L. Scapozza, and G. Folkers J. Recept. Signal. Transduct. 23 2003 361 371
43. O. Nicolotti, T.F. Miscioscia, F. Leonetti, G. Muncipinto, and A. Carotti J. Chem. Inf. Model. 47 2007 2439 2448
44. I. Giangreco, O. Nicolotti, A. Carotti, F. De Carlo, G. Gargano, and R. Bellotti BMC Bioinform. 500 2010 1 13
45. J.M. Chen, F.C. Nelson, J.I. Levin, D. Mobilio, F.J. Moy, R. Nilakantan, A. Zask, and R. Powers J. Am. Chem. Soc. 122 2000 9648 9654
46. J. Wang, S. O'Sullivan, S. Harmon, R. Keaveny, M.W. Radomski, C. Medina, and J.F. Gilmer J. Med. Chem. 55 2012 2154 6212
47. S.C. Lovell, J.M. Word, J.S. Richardson, and D.C. Richardson Proteins 40 2000 389 408 14