4-Alkyliden-β-lactams conjugated to polyphenols: Synthesis and inhibitory activity

Bioorganic and Medicinal Chemistry

Volumn 13, Issue 22, 2005, Pages 6120-6132

  Cainelli, Gianfranco ^a   Galletti, Paola ^a   Garbisa, Spiridione ^b   Giacomini, Daria ^a   Sartor, Luigi ^b   Quintavalla, Arianna ^a  

^a UNIVERSITY OF BOLOGNA   (Italy)

^b UNIVERSITY OF PADOVA   (Italy)

Author keywords

Lactams; Elastase; Gelatinase; Inhibitors; Polyphenols

Indexed keywords

3,5 BISBENZYLOXY 4 HYDROXYBENZOIC ACID 1 (2 BENZYLOXYCARBONYLMETHYLEN 4 OXOAZETIDIN 3 YL)ETHYL ESTER; 4 ALKYLIDEN BETA LACTAM; [3 [1 (TERT BUTYLDIMETHYLSILANYLOXY)ETHYL] 4 OXO 1 (3,4,5 TRISBENZYLOXYBENZOYL)AZETIDIN 2 YLIDENE]ACETIC ACID ETHYL ESTER; BETA LACTAM DERIVATIVE; GELATINASE A; GELATINASE B; LEUKOCYTE ELASTASE; N GALLOYL 4 ALKYLIDEN BETA LACTAM; POLYPHENOL DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; ARYLATION; CONJUGATION; CONTROLLED STUDY; DOSE RESPONSE; DRUG ACTIVITY; DRUG STRUCTURE; DRUG SYNTHESIS; ENZYME ACTIVITY; ENZYME INHIBITION; HUMAN; HUMAN CELL; IC 50; MOLECULE; PHARMACOPHORE;

BETA-LACTAMS; CELL LINE, TUMOR; FLAVONOIDS; HUMANS; LEUKOCYTE ELASTASE; MATRIX METALLOPROTEINASE 2; MATRIX METALLOPROTEINASE 9; METALLOENDOPEPTIDASES; PHENOLS; STRUCTURE-ACTIVITY RELATIONSHIP;

EID: 25844476174     PISSN: 09680896     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.bmc.2005.06.041     Document Type: Article

References (26)

1. B.G. Green, R. Chabin, S. Mills, D.J. Underwood, S.K. Shah, D. Kuo, P. Gale, A.L. Maycock, J. Liesch, C.S. Burgey, J.B. Doherty, C.P. Dorn, P.E. Finke, W.K. Hagmann, J.J. Hale, M. Maccoss, W.M. Westler, and W.B. Knight Biochemistry 34 1995 14331
2. N.C.J. Strynadka, H. Adachi, S.E. Jensen, K. Johns, A. Sielecki, C. Betzel, K. Sutoh, and M.N.G. James Nature 359 1992 700
3. D.G. Tew, H.F. Boyd, S. Ashman, C. Theobald, and C.A. Leach Biochemistry 37 1998 10087
4. M. Paetzel, R.E. Dalbey, and N.C.J. Strynadka Nature 396 1998 186
5. G. Cainelli, D. Giacomini, P. Galletti, and A. Quintavalla Eur. J. Org. Chem. 9 2003 1765
6. G. Cainelli, P. Galletti, S. Garbisa, D. Giacomini, L. Sartor, and A. Quintavalla Biorg. Med. Chem. 11 2003 5391
7. S.A. Eccles, G.M. Box, W.J. Court, E.A. Bone, W. Thomas, and P.D. Brown Cancer Res. 56 1996 2815
8. L.M. Coussens, B. Fingleton, and L.M. Matrisian Science 295 2002 2387
9. Z.Y. Wang, M.T. Huang, C.T. Ho, R. Chang, W. Ma, T. Ferraro, K.R. Reuhl, C.S. Yang, and A.H. Conney Cancer Res. 52 1992 6657
10. Y. Cao, and R. Cao Nature 398 1999 381
11. S. Garbisa, S. Biggin, N. Cavallarin, L. Sartor, R. Benelli, and A. Albini Nat. Med. 5 1999 1216
12. S. Taniguchi, H. Fujiki, H. Kobayashi, H. Go, K. Miyado, H. Sadano, and R. Shimokawa Cancer Lett. 65 1992 51
13. S. Garbisa, L. Sartor, S. Biggin, B. Salvato, R. Benelli, and A. Albini Cancer 91 2001 822
14. M. Demeule, M. Brossard, M. Page, D. Gingras, and R. Beliveau Biochim. Biophys. Acta 1478 2000 51
15. L. Sartor, E. Pezzato, and S. Garbisa J. Leuk. Biol. 71 2002 73
16. G. Cainelli, D. Giacomini, M. Gazzano, P. Galletti, and A. Quintavalla Tetrahedron Lett. 44 2003 6269
17. S. Gerard, M. Galleni, G. Dive, and J. Marchand-Brynaert Bioorg. Med. Chem. 12 2004 129
18. C. Beauve, M. Bouchet, R. Touillaux, J. Fastrez, and J. Marchand-Brynaert Tetrahedron 55 1999 13301
19. Cainelli, Giacomini, Galletti unpublished results.
20. cf. for instance the X-ray structures of complexes between β-lactams and porcine pancreas elastase: P. Taylor, V. Anderson, J. Dowden, S.L. Flitsch, N.J. Turner, K. Loughrans, and M.D. Walkinshaw J. Biol. Chem. 35 1999 24901
21. M.A. Navia, J.P. Springer, T.-Y. Lin, H.R. Williams, R.A. Firestone, J.M. Pisano, J.B. Doherty, P.E. Finke, and K. Hoogsteen Nature 327 1987 79
22. P.L. Durette, R.M. Chabin, D.S. Fletcher, B.G. Green, W.A. Hanlon, J.L. Humes, W.B. Knight, T.J. Lanza Jr., R.A. Mumford, S. Pacholok, and M. MacCoss Bioorg. Med. Chem. Lett. 5 1995 271
23. J.B. Doherty, S.K. Shah, P.E. Finke, C.P. Dorn Jr., W.K. Hagmann, J.J. Hale, A.L. Kissinger, K.R. Thompson, K. Brause, G.O. Chandler, W.B. Knight, A.L. Maycock, B.M. Ashe, H. Weston, P. Gale, R.A. Mumford, O.F. Andersen, H.R. Williams, T.E. Nolan, D.L. Frankenfield, D. Underwood, K.P. Vyas, P.H. Kari, M.E. Dahlgren, J. Mao, D.S. Fletcher, P.S. Dellea, K.M. Hand, D.G. Osinga, L.B. Peterson, D.T. Williams, J.M. Metzger, R.J. Bonney, J.L. Humes, S.P. Pacholok, W.A. Hanlon, E. Opas, J. Stolk, and P. Davies Proc. Natl. Acad. Sci. U.S.A. 90 1993 8727
24. M. Donà, I. Dell'Aica, E. Pezzato, L. Sartor, F. Calabrese, M. Della Barbera, A. Donella-Deana, G. Appendino, A. Borsarini, R. Caniato, and S. Garbisa Cancer Res. 64 2004 6225
25. S.R. Angle, and D.S. Belanger J. Org. Chem. 69 2004 4361 and references cited therein
26. R.L. Danheiser, R.F. Miller, R.G. Brisbois, and S.Z. Park J. Org. Chem. 55 1990 1959