Design, synthesis, and evaluation of novel galloyl pyrrolidine derivatives as potential anti-tumor agents

Bioorganic and Medicinal Chemistry

Volumn 14, Issue 5, 2006, Pages 1287-1293

  Li, Xun ^a   Li, Yalin ^a   Xu, Wenfang ^a  

^a SHANDONG UNIVERSITY   (China)

Author keywords

Anti tumor agents; Galloyl pyrrolidine derivatives; Gelatinase inhibitor; MMPI

Indexed keywords

3 (5 (METHYLOXYCARBONYL) 1 (3,4,5 TRIMETHOXYBENZOYL)PYRROLIDIN 2 YLAMINO)PROPANOIC ACID; 4 (2 (5 (METHYLOXYCARBONYL) 1 (3,4,5 TRIMETHOXYBENZOYL)PYRROLIDIN 2 YLAMINO) 2 OXOETHYL)BENZOIC ACID; 4 (3 (3,4 DIMETHOXYPHENYL)ACRYLAMIDO) N HYDROXY 1 (3,4,5 TRIMETHOXYBENZOYL)PYRROLIDINE 2 CARBOXAMIDE; 4 HEXANAMIDO N HYDROXY 1 (3,4,5 TRIMETHOXYBENZOYL)PYRROLIDINE 2 CARBOXAMIDE; GALLOYL PYRROLIDINE DERIVATIVE; GELATINASE A; GELATINASE B; METHYL 4 (3 (3,4 DIHYDROXYPHENYL)ACRYLAMIDO) 1 (3,4,5 TRIMETHOXYBENZOYL)PYRROLIDINE 2 CARBOXYLATE; METHYL 4 (3 (3,4 DIMETHOXYPHENYL)ACRYLAMIDO) 1 (3,4,5 TRIMETHOXYBENZOYL)PYRROLIDINE 2 CARBOXYLATE; METHYL 4 (3,4,5 TRIHYDROXYBENZAMIDO) 1 (3,4,5 TRIMETHOXYBENZOYL)PYRROLIDINE 2 CARBOXYLATE; METHYL 4 (4 METHOXYSULFONAMIDO) 1 (3,4,5 TRIMETHOXYBENZOYL)PYRROLIDINE 2 CARBOXYLATE; METHYL 4 (METHOXYSULFONYLOXY) 1 (3,4,5 TRIMETHOXYBENZOYL)PYRROLIDINE 2 CARBOXYLATE; METHYL 4 (METHYLSULFONAMIDO) 1 (3,4,5 TRIMETHOXYBENZOYL)PYRROLIDINE 2 CARBOXYLATE; METHYL 4 (NICOTINAMIDO) 1 (3,4,5 TRIMETHOXYBENZOYL)PYRROLIDINE 2 CARBOXYLATE; METHYL 4 AMINO 1 (3,4,5 TRIMETHOXYBENZOYL)PYRROLIDINE 2 CARBOXYLATE; METHYL 4 AZIDO 1 (3,4,5 TRIMETHOXYBENZOYL)PYRROLIDINE 2 CARBOXYLATE; METHYL 4 HEXANAMIDO 1 (3,4,5 TRIMETHOXYBENZOYL)PYRROLIDINE 2 CARBOXYLATE; METHYL 4 HYDROXY 1 (3,4,5 TRIMETHOXYBENZOYL)PYRROLIDINE 2 CARBOXYLATE; METHYL 4 PROPIONAMIDO 1 (3,4,5 TRIMETHOXYBENZOYL)PYRROLIDINE 2 CARBOXYLATE; N HYDROXY 4 (4 METHYLPHENYLSULFONAMIDO) 1 (3,4,5 TRIMETHOXYBENZOYL)PYRROLIDINE 2 CARBOXAMIDE; PYRROLIDINE DERIVATIVE; UNCLASSIFIED DRUG;

ANIMAL EXPERIMENT; ANIMAL MODEL; ANTINEOPLASTIC ACTIVITY; ARTICLE; CONTROLLED STUDY; DRUG DESIGN; DRUG INHIBITION; DRUG MECHANISM; DRUG PROTEIN BINDING; DRUG STRUCTURE; DRUG SYNTHESIS; ENZYME INHIBITION; IC 50; IN VIVO STUDY; MOUSE; NONHUMAN; STRUCTURE ACTIVITY RELATION;

ANIMALS; ANTINEOPLASTIC AGENTS; DRUG DESIGN; GELATINASES; INHIBITORY CONCENTRATION 50; MICE; NEOPLASM METASTASIS; PROTEIN BINDING; PYRROLIDINES; STRUCTURE-ACTIVITY RELATIONSHIP; TUMOR CELLS, CULTURED;

ANIMALIA;

EID: 31044453202     PISSN: 09680896     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.bmc.2005.09.031     Document Type: Article

References (23)

1. J.W. Skiles, N.C. Gonnella, and A.Y. Jeng Curr. Med. Chem. 8 2001 425
2. N. Ramnath, and P. Creaven J. Curr. Oncol. Rep. 6 2004 96
3. G. Fontanini, L. Boldrini, S. Chine, F. Pisaturo, F. Basolo, A. Calcinai, M. Lucchi, A. Mussi, C.A. Angeletti, and G. Bevilacqua Br. J. Cancer 79 1999 363
4. A.F. Chambers, and L. Matrisian J. Natl. Cancer Inst. 89 1997 1260
5. N.E. Sounni, M. Janssen, and J.M. Foidart Matrix Biol. 22 2003 55
6. H. Sato, T. Takino, and Y. Okada Nature 370 1994 61
7. W.G. Stetler-Stevenson, S. Aznavoorian, and L.A. Liotta Annu. Rev. Cell Biol. 9 1993 541
8. F. Sabeh, I. Ota, K. Holmbeck, H. Birkedal-Hansen, P. Soloway, M. Balbin, C. Lopez-Otin, S. Shapiro, M. Inada, S. Krane, E. Allen, D. Chung, and S.J. Weiss J. Cell Biol. 167 2004 769
9. A.E. Yu, R.E. Hewitt, E.W. Connor, and W.G. Stetler-Stevenson Drugs Aging 11 1997 229
10. M.R. Michaelides, and M.L. Curtin Curr. Pharm. Des. 5 1999 787
11. K. Ferrante, B. Winograd, and R. Canetta Cancer Chemother. Pharmacol. 43 1999 S61
12. M.G. Selzer, B. Zhu, N.L. Block, and B.L. Lokeshwar Ann. N.Y. Acad. Sci. 878 1999 678
13. J.W. Becker, A.I. Marcy, L.L. Rokosz, M.G. Axel, J.J. Burbaum, P.M.D. Fitzgerald, P.M. Cameron, C.K. Esser, W.K. Hagmann, J.D. Hermes, and J.P. Springer Protein Sci. 4 1995 1966
14. N. Motowo Tanpakushitsu Kakusan Koso 45 2000 1083
15. F. Xu, D.Q. Song, and Y.S. Zhen B. Xu J.H. Xu Progress of Anti-Neoplasm-Drugs and Chemotherapy 1st ed. 2001 Science Press Beijing 243 253
16. B. Lovejoy, A.R. Welch, S. Carr, C. Luong, C. Broke, R.T. Hendricks, J.A. Campbell, K.A. Walker, R. Martin, H. Van-Wart, and M.F. Browner Nat. Struct. Biol. 6 1999 217
17. H. Nagase, K. Sasaki, H. Kito, A. Haga, and T. Sato Planta Med. 64 1998 216
18. M. Maeda-Yamamoto, H. Kawahara, N. Tahara, K. Tsuji, Y. Hara, and M. Isemura J. Agric. Food Chem. 47 1999 2350
19. SYBYL6.91, Tripos Associates.1699 S. Hanley Road, Suite 303. St. Louis, MO 63144-2913, 2003.
20. Y. Feng, J.J. Likos, L. Zhu, H. Woodward, G. Munie, J.J. McDonald, A.M. Stevens, C.P. Howard, G.A. De Crescenzo, D. Welsch, H.S. Shieh, and W.C. Stallings Biochim. Biophys. Acta 1598 2002 10
21. I. Svab, D. Alexandru, G. Vitos, and M.L. Flonta J. Cell. Mol. Med. 8 2004 551
22. U. Jordis, F. Sauter, and S.M. Siddiqi Indian J. Chem. Soc. B 28 1989 294
23. M.B. Vijaykumar, J.S. Bonnie, R.R. Richard, J.K. Paul, G.W. Howard, M. Mahesh, R.C. Jon, and K.R. Srinivasa Matrix Biol. 19 2000 26