A novel amino-benzosuberone derivative is a picomolar inhibitor of mammalian aminopeptidase N/CD13

Bioorganic and Medicinal Chemistry

Volumn 19, Issue 18, 2011, Pages 5716-5733

  Maiereanu, Carmen ^a   Schmitt, Céline ^a   Schifano Faux, Nadge ^b   Le Nouën, Didier ^a   Defoin, Albert ^a   Tarnus, Céline ^a  

^a UNIVERSITÉ DE HAUTE ALSACE   (France)

^b UNIV LILLE   (France)

Author keywords

Aminobenzoheptenone; Aminopeptidase N inhibitor; APN CD13

Indexed keywords

1 BROMO 2,3 BIS(BROMOMETHYL)BENZENE; 1 BROMO 4 PHENYL 5,6,8,9 TETRAHYDROBENZOCYCLOHEPTEN 7 ONE; 1 BROMO 5,6,8,9 TETRAHYDROBENZOCYCLOHEPTEN 7 ONE; 1 BROMO 6 HYDROXY 5,6,8,9 TETRAHYDROBENZOCYCLOHEPTEN 8 HYDROXYIMINE; 1 CHLORO 2,3 BIS(BROMOMETHYL)BENZENE; 1 CHLORO 5,6,8,9 TETRAHYDROBENZOCYCLOHEPTEN 7 ONE; 1 CHLORO 6 (TRIMETHYLSILYLOXY) 5,6,8,9 TETRAHYDROBENZOCYCLOHEPTEN 7 ONE; 1 CHLORO 7 TRIMETHYLSILYLOXY 6,9 DIHYDRO 5H BENZOCYCLOHEPTENE; 1,2 BIS BROMOMETHYL NAPHTHALENE; 1,4 DIBROMO 2,3 BIS(BROMOMETHYL)BENZENE; 1,4 DIBROMO 2,3 DIMETHYL BIPHENYLE; 1,4 DIBROMO 2,3 DIMETHYLBENZENE; 1,4 DIBROMO 5,6,8,9 TETRAHYDROBENZOCYCLOHEPTEN 7 ONE; 4 BROMO 2,3 BIS(BROMOMETHYL)BIPHENYLE; 4 BROMO 2,3 DIMETHYBENZENEDIAZONIUM TETRAFLUOROBORATE; 4 BROMO 2,3 DIMETHYLANILINE HYDROBROMIDE; 4 BROMO 6 HYDROXY 1 PHENYL 5,6,8,9 TETRAHYDROBENZOCYCLOHEPTEN 7 HYDROXYIMINE; 4 BROMO 6 HYDROXY 5,6,8,9 TETRAHYDROBENZOCYCLOHEPTEN 7 HYDROXYIMINE; 4 CHLORO 6 (TRIMETHYLSILYLOXY) 5,6,8,9 TETRAHYDROBENZOCYCLOHEPTEN 7 ONE; 4 CHLORO 7 TRIMETHYLSILYLOXY 6,9 DIHYDRO 5H BENZOCYCLOHEPTENE; 7,8,10,11 TETRAHYDRO CYCLOHEPTA[A] NAPHTHALEN 9 ONE; AMINO BENZOSUBERONE DERIVATIVE; AMINOPEPTIDASE; DIMETHYL 1 BROMO 4 PHENYL 7 OXO 5,6,8,9 TETRAHYDRO BENZOCYCLOHEPTEN 6,8 DICARBOXYLIC ACID; DIMETHYL 1 BROMO 7 OXO 5,6,8,9 TETRAHYDRO BENZOCYCLOHEPTEN 6,8 DICARBOXYLIC ACID; DIMETHYL 1 CHLORO 7 OXO 5,6,8,9 TETRAHYDRO BENZOCYCLOHEPTEN 6,8 DICARBOXYLIC ACID; DIMETHYL 1,4 DIBROMO 7 OXO 5,6,8,9 TETRAHYDRO BENZOCYCLOHEPTEN 6,8 DICARBOXYLIC ACID; DIMETHYL 9 OXO 7,8,10,11 TETRAHYDRO NAPHTHOCYCLOHEPTENE 8,10 DICARBOXYLIC ACID; ENZYME INHIBITOR; UNCLASSIFIED DRUG; UNINDEXED DRUG;

ARTICLE; CARBON NUCLEAR MAGNETIC RESONANCE; CATALYSIS; CHEMICAL REACTION; DECARBOXYLATION; DEPROTECTION REACTION; DRUG CONFORMATION; DRUG SCREENING; DRUG STRUCTURE; DRUG SYNTHESIS; ENZYME INHIBITION; HUMAN; HYDROPHOBICITY; NONHUMAN; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY;

AEROMONAS; ANIMALS; ANISOLES; ANTIGENS, CD13; CYCLOHEPTANES; DOSE-RESPONSE RELATIONSHIP, DRUG; ENZYME INHIBITORS; KIDNEY; MOLECULAR STRUCTURE; STEREOISOMERISM; STRUCTURE-ACTIVITY RELATIONSHIP; SWINE;

MAMMALIA;

EID: 80052588946     PISSN: 09680896     EISSN: 14643391     Source Type: Journal    
DOI: 10.1016/j.bmc.2011.06.089     Document Type: Article

References (46)

1. A.J. Barret, N.D. Rawling, and J.F. Woessner 2nd ed. Handbook of Proteolytic Enzymes Vol. 2 2004 Elsevier Academic Press Oxford p 233sq
2. P. Mina-Osorio Trends Mol. Med. 14 2008 361
3. S.V. Bhagwat, J. Lahdenranta, R. Giordano, W. Arap, and R. Pasqualini Blood 97 2001 652
4. S.V. Bhagwat, N. Petrovic, Y. Okamoto, and L.H. Shapiro Blood 101 2003 1818
5. N. Petrovic, W. Schacke, J.R. Gahagan, C.A. O'Conor, B. Winnicka, R.E. Conway, P. Mina-Osorio, and L.H. Shapiro Blood 110 2007 142
6. M. Terauchi, H. Kajiyama, K. Shibata, K. Ino, A. Nawa, S. Mizutani, and F. Kikkawa BMC Cancer 7 2007 140
7. J. Langner, C. Mueller, D. Riemann, and M. Löhn Immunol. Lett. 56 1997 62
8. M. Yamashita, H. Kajiyama, M. Terauchi, K. Shibata, K. Ino, A. Nawa, S. Mizutani, and F. Kikkawa Int. J. Cancer 120 2007 2243
9. K. Fukasawa, H. Fujii, Y. Saitoh, K. Koizumi, Y. Aozuka, K. Sekine, M. Yamada, I. Saiki, and K. Nishikawa Cancer Lett. 243 2006 135
10. R. Rangel, Y. Sun, L. Guzman-Rojas, M.G. Ozawa, J. Sun, R.J. Giordano, C.S. Van Pelt, P.T. Tinkey, R.R. Behringer, R.L. Sidman, W. Arap, and R. Pasqualini Proc. Natl. Acad. Sci. 104 2007 4588
11. D. Riemann, A. Kehlen, and J. Langner Immunol. Today 20 1999 83
12. U. Bank, A. Heimburg, M. Helmuth, S. Stefin, U. Lendeckel, D. Reinhold, J. Faust, P. Fuchs, B. Sens, K. Neubert, M. Täger, and S. Ansorge Int. Immunopharmacol. 6 2006 1925
13. P.D. Matteo, G.L. Arrigoni, L. Alberici, A. Corti, C. Gallo-Stampino, C. Traversari, C. Doglioni, and G.-P. Rizzardi J. Histochem. Cytochem. 59 2011 47
14. D. Reinhold, A. Biton, S. Pieper, U. Lendeckel, J. Faust, K. Neubert, U. Bank, M. Täger, S. Ansorge, and S. Brocke Int. Immunopharmacol. 6 2006 1935
15. A. Mucha, M. Drg, J.P. Dalton, and P. Kafarski Biochimie 92 2010 1509
16. B. Bauvois, and D. Dauzonne Med. Chem. Rev. 26 2006 88
17. F.E. Jacobsen, J.A. Lewis, and S.M. Cohen Chem. Med. Chem. 2 2007 152
18. S. Albrecht, M. Al-Lakkis-Wehbe, A. Orsini, A. Defoin, P. Pale, E. Salomon, C. Tarnus, and J.-M. Weibel Bioorg. Med. Chem. 19 2011 1434
19. A.L. Hopkins, C.R. Groom, and A. Alex Drug Discovery Today 9 2004 430
20. M. Matsui, J.H. Fowler, and L.L. Walling Biol. Chem. 387 2006 1535
21. A.J. Barret, N.D. Rawling, and J.F. Woessner 2nd ed. Handbook of Proteolytic Enzymes Vol. 2 2004 Elsevier Academic Press Oxford p 253 sq
22. Y.-H. Lai, and A.H.-T. Yap J. Chem. Soc., Perkin Trans. 2 1993 1373
23. S. Sengupta, and S. Bhattacharyya J. Org. Chem. 62 1997 3405
24. S. Kajigaeshi, T. Kakinami, T. Okamoto, H. Nakamura, and M. Fujikawa Bull. Chem. Soc. Jpn. 60 1987 4187
25. G. Simchen, and W. Kober Synthesis 1976 259
26. Y. Taniguchi, J. Inanaga, and M. Yamaguchi Bull. Chem. Soc. Jpn. 154 1981 3229
27. A. Hassner, R.H. Reuss, and H.W. Pinnick J. Org. Chem. 40 1975 3427
28. G.M. Rubottom, M.A. Vasquez, and D.R. Pelegrina Tetrahedron Lett. 15 1974 4319
29. B. Miriyala, S. Bhattacharyya, and J. Williamson Tetrahedron 60 2004 1463
30. R.K. Boeckman Jr., P. Shao, and J.J. Mullins Org. Synth. 77 2000 141
31. D.B. Dess, and J.C. Martin J. Org. Chem. 48 1983 4155 www.SyntheticPages.org/pages/51
32. P. Auffinger, F.A. Hays, E. Westhof, and H.P. Shing Proc. Natl. Acad. Sci. 101 2004 16789
33. M.Z. Harnandes, S.M.T. Cavalcanti, D.R.M. Moreira, W.F. de Azevedo Jr., and A.C.L. Leite Curr. Drug Targets 11 2010 303
34. C. Schalk, H. d'Orchymont, M.-F. Jauch, and C. Tarnus Arch. Biochem. Biophys. 311 1994 42
35. d'Orchymont, H.; Tarnus, C. Eur. Patent 0378456 A1, 1990.
36. S. Albrecht, A. Defoin, E. Salomon, C. Tarnus, A. Wetterholm, and J.Z. Haeggström Bioorg. Med. Chem. 14 2006 7241
37. R. Himmelhoch, and S.A. Peterson Biochemistry 7 1968 2085
38. C.A. Lipinski, F. Lombardo, B.W. Dominy, and P.J. Feeney Adv. Drug Deliv. Rev. 46 2001 3
39. T.S. Skinner-Adams, C.M. Stack, K.R. Trenholme, C.L. Brown, J. Grembecka, J. Lowther, A. Mucha, M. Drg, P. Kafarski, S. McGowan, J.C. Whisstock, D.L. Gardiner, and J.P. Dalton Trends Biochem. Sci. 35 2010 53
40. A.S. Dey, A. Rosowsky, and E.J. Modest J. Org. Chem. 35 1970 536
41. J.A. McCauley, C.J. McIntyre, M.T. Rudd, K.T. Nguyen, J.J. Romano, J.W. Butcher, K.F. Gilbert, K.J. Bush, M.K. Holloway, J. Swestock, B.-L. Wan, S.S. Carroll, J.M. DiMuzio, D.J. Graham, S.W. Ludmerer, S.-S. Mao, M.W. Stahlhut, C.M. Fandozzi, N. Trainor, D.B. Olsen, J.P. Vacca, and N.J. Liverton J. Med. Chem. 53 2010 2443
42. H. Tsue, S. Nakashima, Y. Goto, H. Tatemitsu, S. Misumi, R.J. Abraham, T. Asahi, Y. Tanaka, T. Okada, N. Mataga, and Y. Sakata Bull. Chem. Soc. Jpn. 67 1994 3067
43. A. Wu, A. Chakraborty, D. Witt, J. Lagona, F. Damkaci, M.A. Ofori, J.K. Chiles, J.C. Fettinger, and L. Isaacs J. Org. Chem. 67 2002 5817
44. W. Ried, and H. Bodem Liebigs Ann. Chem. 589 1954 55
45. S. Ohkawa, B. DiGiacomo, D.L. Larson, A.E. Takemori, and P.S. Portoghese J. Med. Chem. 40 1997 1720
46. I.H. Segel Enzyme Kinetics 1993 John Wiley & Son New-York