Rapid and efficient synthesis of a novel series of substituted aminobenzosuberone derivatives as potent, selective, non-peptidic neutral aminopeptidase inhibitors

Bioorganic and Medicinal Chemistry

Volumn 20, Issue 16, 2012, Pages 4942-4953

  Albrecht, Sébastien ^a   Salomon, Emmanuel ^a   Defoin, Albert ^a   Tarnus, Céline ^a  

^a Ecole Nationale Superieure de Chimie de Mulhouse   (France)

Author keywords

Aminopeptidase N inhibitor; APN CD13; Racemic 5 substituted aminobenzocycloheptenone

Indexed keywords

3 AMINO 2 BENZOSUBERONE; 3 AMINO 2 BENZOSUBERONE DERIVATIVE; 5 PHENYLETHYL 7 AMINO 5,7,8,9 TETRAHYDROBENZOCYCLOHEPTEN 6 ONE; 5 PHENYLPROPYL 7 AMINO 5,7,8,9 TETRAHYDROBENZOCYCLOHEPTEN 6 ONE; 5 PHENYLTHIO 7 AMINO 5,7,8,9 TETRAHYDROBENZOCYCLOHEPTEN 6 ONE; 7 AMINO 5 BENZYL 5,7,8,9 TETRAHYDROBENZOCYCLOHEPTEN 6 ONE; 7 AMINO 5 BENZYLIDENE 5,7,8,9 TETRAHYDROBENZOCYCLOHEPTEN 6 ONE; 7 AMINO 5 BENZYLTHIO 5,7,8,9 TETRAHYDROBENZOCYCLOHEPTEN 6 ONE; 7 AMINO 5 FLUORO 5,7,8,9 TETRAHYDROBENZOCYCLOHEPTEN 6 ONE; AMINOPEPTIDASE; BESTATIN; PEPTIDE HYDROLASE INHIBITOR; UNCLASSIFIED DRUG;

ARTICLE; CONTROLLED STUDY; DRUG DESIGN; DRUG POTENCY; DRUG SELECTIVITY; DRUG STRUCTURE; DRUG SYNTHESIS; ENZYME INHIBITION; STRUCTURE ACTIVITY RELATION;

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

MAMMALIA;

EID: 84864442047     PISSN: 09680896     EISSN: 14643391     Source Type: Journal    
DOI: 10.1016/j.bmc.2012.06.041     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 233
2. M. Drag, M. Bogyo, J.A. Ellman, and J.S. Salvesen J. Biol. Chem. 285 2010 3310
3. P. Mina-Osorio Trends Mol. Med. 14 2008 361
4. S.V. Bhagwat, J. Lahdenranta, R. Giordano, W. Arap, and R. Pasqualini Blood 97 2001 652
5. S.V. Bhagwat, N. Petrovic, Y. Okamoto, and L.H. Shapiro Blood 2003 1818 101
6. 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
7. M. Terauchi, H. Kajiyama, K. Shibata, K. Ino, A. Nawa, S. Mizutani, and F. Kikkawa BMC Cancer 7 2007 140
8. J. Langner, C. Mueller, D. Riemann, and M. Löhn Immunol. Lett. 56 1997 62
9. M. Yamashita, H. Kajiyama, M. Terauchi, K. Shibata, K. Ino, A. Nawa, S. Mizutani, and F. Kikkawa Int. J. Cancer 120 2007 2243
10. K. Fukasawa, H. Fujii, Y. Saitoh, K. Koizumi, Y. Aozuka, K. Sekine, M. Yamada, I. Saiki, and K. Nishikawa Cancer Lett. 243 2006 135
11. 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
12. A. Mucha, M. Drag, J.P. Dalton, and P. Kafarski Biochimie 92 2010 1509
13. B. Bauvois, and D. Dauzonne Med. Chem. Rev. 26 2006 88
14. F.E. Jacobsen, J.A. Lewis, and S.M. Cohen Chem. Med. Chem. 2 2007 152
15. J.S. Shim, J.H. Kim, H.Y. Cho, Y.N. Yum, S.H. Kim, H.J. Park, B.S. Shim, S.H. Choi, and H. Kwon J. Chem. Biol. 10 2003 695
16. D. Kim, I.S. Lee, J.H. Jung, C.O. Lee, and S.U. Choi Anticancer Res. 19 1999 4085
17. B. Bauvois, M.L. Puiffe, J.B. Bongui, S. Paillat, C. Monneret, and D. Dauzonne J. Med. Chem. 46 2003 3900
18. R. Grzywa, J. Oleksyszyn, G.S. Salvesen, and M. Drag Bioorg. Med. Chem. 20 2010 2497
19. C. Schalk, H. d'Orchymont, M.-F. Jauch, and C. Tarnus Arch. Biochem. Biophys. 311 1994 42
20. H. d'Orchymont, and C. Tarnus Eur. Patent 0378456 1990 A1
21. S. Albrecht, A. Defoin, E. Salomon, C. Tarnus, A. Wetterholm, and J.Z. Haeggström Bioorg. Med. Chem. 14 2006 7241
22. S. Albrecht, M. Al-Lakkis-Wehbe, A. Orsini, A. Defoin, P. Pale, E. Salomon, C. Tarnus, and J.-M. Weibel Bioorg Med Chem. 119 2011 1434
23. C. Maiereanu, C. Schmitt, N. Schifano-Faux, D. Le Nouën, A. Defoin, and C. Tarnus Bioorg. Med. Chem. 19 2011 5716
24. Tarnus-Rondeau, C.; Defoin, A.; Albrecht, S.; Maiereanu, C.; Faux, N.; Pale, P. French Patent: FR2908131, W2008059141, Dérivés d'aminobenzocycloheptènes, leurs procédés de préparation et leur utilisation en thérapeutique.
25. N.L. Allinger, and W. Szkrybalo J. Org. Chem. 27 1962 722
26. G.A. Russell, R.L. Blankespoor, K.D. Trahanovsky, C.S.C. Chung, P.R. Whittle, J. Mattox, C.L. Myers, R. Penny, T. Ku, Y. Kosugi, and R.S. Givens J. Am. Chem. Soc. 1975 1906 97
27. S. Mataka, K. Takahashi, T. Mimura, T. Hirota, K. Takuma, H. Kobayashi, and M. Tashiro J. Org. Chem. 52 1987 2653
28. R.P. Singh, and J.M. Shreeve Acc. Chem. Res. 37 2004 31
29. P.T. Nyffeler, S.G. Durón, M.D. Burkart, S.P. Vincent, and C.-H. Wong Angew. Chem. Int. Ed. 44 2005 192
30. A.G. Gilicinski J. Fluorine Chem. 59 1992 157
31. R.E. Banks J. Fluorine Chem. 87 1998 1
32. C.K. Larock, T.R. Hightower, G.A. Kraus, P. Hahn, and D. Zheng Tetrahedron Lett. 36 1995 2423
33. B. Miriyala, S. Bhattacharyya, and J. Williamson Tetrahedron 60 2004 1463
34. E.P. Siqueira Filho, J.A. Rodrigues, and P. Moran J. Tetrahedron: Asymmetry 12 2001 847
35. M.Y. Kim, G.J. Lim, D.S. Kim, I.Y. Kim, and J.S. Yang Heterocycles 45 1997 2041
36. Leong, M.; Mastryukov, V.; Boggs, J. J. Mol. Struct. 1998, 445, 149. From the given dihedral angles it is possible to calculate the dihedral angles between the different protons. For the chair conformation: (7,8a) 185°; (7,8e) 65°; (8a,9a) 195°; (8a,9e) = (8e,9a) 75°; (8e,9e) 45°. For the boat conformation: (7,8a) 176°; (7,8e) 56°; (8e,9a) 148°; (8a,9e) 82°; (8e,9e) = (8a,9a) 28°.
37. I.H. Segel Enzyme Kinetics 1993 John Wiley & Son New-York
38. J.W. Williams, and J.F. Morrison Methods Enzymol. 1979 63437
39. S. Cha Biochem. Pharmacol. 24 1975 2177
40. J.V. Schloss Acc. Chem. Res. 1988 21348
41. R. Paulini, K. Müller, and F. Diederich Angew. Chem. Int. Ed. 44 2005 1788
42. T. Ocain, and D.J. Rich J. Med. Chem. 31 1988 2193
43. E.M. Gordon, J.D. Godfrey, N.G. Delaney, M.M. Asaad, D. Von Langen, and D.W. Cushman J. Med. Chem. 31 1988 2199
44. R.E. Ireland, and L. Liu J. Org. Chem. 58 1993 2899
45. D. Dess, and J. Martin J. Am. Chem. Soc. 113 1991 7277
46. R. Himmelhoch, and S.A. Peterson Biochemistry 7 1968 2085