Iodine(III)-mediated ring expansion: An efficient and green pathway in the synthesis of a key precursor for the design of aminopeptidase (APN or CD13) inhibitors

Tetrahedron

Volumn 66, Issue 45, 2010, Pages 8722-8728

  Roux, Lionel ^a   Charrier, Cédric ^a   Defoin, Albert ^a   Bisseret, Philippe ^a   Tarnus, Céline ^a  

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

Author keywords

Aminopeptidase; APN or CD13 inhibitors; Hypervalent iodine chemistry; Ring expansion

Indexed keywords

1 (2,2,2 TRIFLUOROACETYLAMINO) 7 ETHOXYCARBONYLAMINO 5,7,8,9 TETRAHYDRO 6H BENZOCYCLOHEPTEN 6 ONE; 1 (TERT BUTOXYCARBONYLAMINO) 4 BROMO 7 BENZYLOXY CARBONYLAMINO 5,7,8,9 TETRAHYDRO 6H BENZOCYCLOHEPTEN 6 ONE; 1 (TERT BUTOXYCARBONYLAMINO) 7 BENZOXYCARBONYLAMINO 5,7,8,9 TETRAHYDRO 6H BENZOCYCLOHEPTEN 6 OL; 1 (TERT BUTOXYCARBONYLAMINO) 7 BENZYLOXYCARBONYLAMINO 5,7,8,9 TETRAHYDRO 6H BENZOCYCLOHEPTEN 6 ONE; 1 (TERT BUTOXYCARBONYLAMINO) 7 ETHOXYCARBONYLAMINO 5,7,8,9 TETRAHYDRO 6H BENZOCYCLOHEPTEN 6 OL; 1 (TERT BUTOXYCARBONYLAMINO) 7 ETHOXYCARBONYLAMINO 5,7,8,9 TETRAHYDRO 6H BENZOCYCLOHEPTEN 6 ONE; 2 ETHOXYCARBONYLAMINO 4 [2 (2,2,2 TRIFLUOROACETYLAMINO)PHENYL] BUTANOIC ACID; 2 ETHOXYCARBONYLAMINO 4 OXO 4 [2 (2,2,2 TRIFLUOROACETYLAMINO) PHENYL] BUTANOIC ACID; ALKYL GROUP; BENZENE DERIVATIVE; CYCLOHEXANE DERIVATIVE; ETHYL (2 OXO 2,3,4,5 TETRAHYDRO 1H BENZO[B]AZEPIN 3 YL)CARBAMATE; ETHYL [1 METHYLEN 5 (2,2,2 TRIFLUOROACETYLAMINO) 1,2,3,4 TETRAHYDRO NAPHTHALEN 2 YL]CARBAMATE; ETHYL [1 OXO 5 (2,2,2 TRIFLUOROACETYLAMINO) 1,2,3,4 TETRAHYDRONAPHTHALEN 2 YL]CARBAMATE; IODINE DERIVATIVE; METHYLIDENEBENZOCYCLOHEXANE DERIVATIVE; MICROSOMAL AMINOPEPTIDASE; MICROSOMAL AMINOPEPTIDASE INHIBITOR; N (ETHOXYCARBONYL)TRYPTOPHANE METHYL ESTER; NAPHTHALENE DERIVATIVE; PEPTIDE HYDROLASE INHIBITOR; TRYPTOPHAN DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL REACTION; CHEMICAL STRUCTURE; DERIVATIZATION; DRUG DESIGN; DRUG STRUCTURE; DRUG SYNTHESIS; PRECURSOR; PRIORITY JOURNAL; REACTION ANALYSIS; WITTIG REACTION;

EID: 77958020967     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tet.2010.09.005     Document Type: Article

References (21)

1. P. Mina-Osorio Trends Mol. Med. 14 2008 361 371
2. X. Zhang, and W. Xu Curr. Med. Chem. 15 2008 2850 2865
3. G. Bergers, and L.E. Benjamin Nat. Rev. Cancer 3 2003 401 410
4. B. Bauvois, and D. Dauzonne Med. Res. Rev. 26 2006 88 130
5. R. Pasqualini, E. Koivunen, R. Kain, J. Lahdenranta, M. Sakamoto, A. Stryhn, R.A. Ashmun, L.H. Shapiro, W. Arap, and E. Ruoslahti Cancer Res. 60 2000 722 727
6. Dérivés d'aminobenzocycloheptne, leurs procé dés de préparation et leur utilisation en thérapeutique. Albrecht, S.; Maiereanu, A.; Faux, N.; Tarnus-Rondeau, C.; Defoin, A.; Pale, P. WO2008059141 (A1).
7. A.L. Hopkins, C.R. Groom, and A. Alex Drug Discvery Today 9 2004 430 431
8. 4-Bromobenzosuberone derivative 2 is in particular ideally substituted for further pallado-catalyzed coupling experiments.
9. E.C. Taylor, and C.-S. Chiang Tetrahedron Lett. 21 1977 1827 1830
10. M.W. Justik, and G.F. Koser Tetrahedron Lett. 45 2004 6159 6163
11. M.W. Justik, and G.F. Koser Molecules 10 2005 217 225
12. Iodine(III)-promoted ring expansion of 1-vinylcycloalkanols was recently used for the synthesis of seven-membered ring methoxylated ketones: L.F. Silva Jr., R.S. Vasconcelos, and M.A. Nogueira Org. Lett. 10 2008 1017 1020 Although closely related to our approach, this latter work did not imply methylidene derivatives as in our case but vinylcycloalkanols
13. S. De Lombaert, L. Blanchard, L.B. Stamford, D.M. Sperbeck, M.D. Grim, T.M. Jenson, and H.R. Rodriguez Tetrahedron Lett. 35 1994 7513 7516
14. M.A. Carr, P.E. Creviston, D.R. Hutchison, J.H. Kennedy, V.V. Khau, T.J. Kress, M.R. Leanna, J.D. Marshall, M.J. Martinelli, B.C. Peterson, D.L. Varie, and J.P. Wepsiec J. Org. Chem. 62 1997 8640 8653
15. K.-Y. Lin, and M.D. Matteucci J. Am. Chem. Soc. 120 1998 8531 8532
16. R.C. Hartley, J. Li, C.A. Main, and G.J. McKiernan Tetrahedron 63 2007 4825 4864
17. C.H. Park, D.R. Brittelli, C.L.J. Wang, F.D. Marsh, W.A. Gregory, M.A. Wuonola, R.J. McRipley, V.S. Eberly, A.M. Slee, and M. Forbes J. Med. Chem. 35 1992 1156 1165
18. N.S. Chowdari, and C.F. Barbas III Org. Lett. 7 2005 867 870
19. S. Raucher, B.L. Bray, and R.F. Lawrence J. Am. Chem. Soc. 109 1987 442 445
20. P.M. Wovkulich, and M.R. Uskokovic Tetrahedron 41 1985 3455 3462
21. N. Lewis, A. McKillop, R.J.K. Taylor, and R.J. Watson Synth. Commun. 25 1995 561 568