Design and synthesis of indole and tetrahydroisoquinoline hydantoin derivatives as human chymase inhibitors

Journal of Enzyme Inhibition and Medicinal Chemistry

Volumn 19, Issue 2, 2004, Pages 137-143

  Alagille, David ^a,b   Pfeiffer, Bruno ^c   Scalbert, Elizabeth ^c   Ferry, Gilles ^d   Boutin, Jean A ^d   Renard, Pierre ^c   Viaud Massuard, Marie Claude ^a  

^a UNIVERSITÉ DE TOURS   (France)

^b UNIVERSITÉ D'ORLÉANS   (France)

^c INSTITUT DE RECHERCHES INTERNATIONALES SERVIER   (France)

^d INSTITUT DE RECHERCHES SERVIER   (France)

Author keywords

Human chymase; Indoles; Inhibitors; Tetrahydroisoquinoline hydantoins

Indexed keywords

2 (2 NAPHTHYLSULFONYL) 10,10A DIHYDROIMIDAZO[1,5 B]ISOQUINOLINE 1,3(2H,5H) DIONE; 2 (2 NAPHTHYLSULFONYL) 1H IMIDAZO[1,5 A]INDOLE 1,3(2H) DIONE; 2 (2 NAPHTHYLSULFONYL) 9,9A DIHYDRO 1H IMIDAZO[1,5 A]INDOLE 1,3(2H) DIONE; 2 (3,4 DICHLOROPHENYLSULFONYL) 1H IMIDAZO[1,5 A]INDOLE 1,3(2H) DIONE; 2 (3,4 DICHLOROPHENYLSULFONYL) 9,9A DIHYDRO 1H IMIDAZO[1,5 A]INDOLE 1,3(2H) DIONE; 2 (3,4 DIMETHYLPHENYLSULFONYL) 10,10A DIHYDROIMIDAZO[1,5 B]ISOQUINOLINE 1,3(2H,5H) DIONE; 2 (3,4 DIMETHYLPHENYLSULFONYL) 1H IMIDAZO[1,5 A]INDOLE 1,3(2H) DIONE; 2 (3,4 DIMETHYLPHENYLSULFONYL) 9,9A DIHYDRO 1H IMIDAZO[1,5 A]INDOLE 1,3(2H) DIONE; 2 (4 METHYLPHENYLSULFONYL) 10,10A DIHYDROIMIDAZ[1,5 B]ISOQUINOLINE 1,3(2H,5H) DIONE; 2 (4 METHYLPHENYLSULFONYL) 1H IMIDAZO[1,5 A]INDOLE 1,3(2H) DIONE; 2 (4 METHYLPHENYLSULFONYL) 9,9A DIHYDRO 1H IMIDAZO[1,5 A]INDOLE 1,3(2H) DIONE; CHYMASE INHIBITOR; HYDANTOIN DERIVATIVE; IMIDAZOLE DERIVATIVE; INDOLE DERIVATIVE; POLYCYCLIC AROMATIC HYDROCARBON DERIVATIVE; TETRAHYDROISOQUINOLINE DERIVATIVE; THIOL; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL REACTION; DRUG DESIGN; DRUG SYNTHESIS; ENZYME INHIBITION; HUMAN; OXIDATION; PRIORITY JOURNAL;

ANIMALS; CERCOPITHECUS AETHIOPS; CHYMASES; COS CELLS; ENZYME INHIBITORS; HUMANS; HYDANTOINS; INDOLES; KINETICS; MODELS, MOLECULAR; MOLECULAR CONFORMATION; RECOMBINANT PROTEINS; SERINE ENDOPEPTIDASES; SERINE PROTEINASE INHIBITORS; TETRAHYDROISOQUINOLINES; TRANSFECTION;

EID: 2942612738     PISSN: 14756366     EISSN: None     Source Type: Journal    
DOI: 10.1080/14756360310001650200     Document Type: Article

References (14)

1. Wang, Z., Walter, M., Selwood, T., Rubin, H. and Schechter, N.M. (1998) Biol. Chem. 379, 167.
2. Schechter, N.M., Fräki, J.E,, Geesin, J.C. and Lazarus, G.S. (1983) J. Biol. Chem. 258, 2973.
3. Okunishi, H., Miyazaki, M., Okamura, T. and Toda, N. (1987) Biochem. Biophys. Res. Commun. 149, 1186.
4. Wolny, A., Clozel, J.P., Mory, P., Vogt, P., Turino, M., Kiowski, W. and Fischli, W. (1991) Circulation Res. 80, 219.
5. Saarinen, J., Kalkkinnen, N., Welgus, H.G. and Kovanen, P.T. (1994) J. Biol. Chem. 269, 18134.
6. Urata, H., Kinoshita, A., Misono, K.S., Bumpus, F.M. and Husain, A. (1990) J. Biol. Chem. 265, 22348.
7. Powers, J.C., Tanaka, T., Harper, J.W., Minematsu, Y., Barker, L., Lincoln, D., Crumley, K.V., Fraki, J.E., Schechter, N.M., Lazarus, G.G., Nakajima, K., Nakashino, K., Neurath, H. and Woodbury, R.G. (1985) Biochemistry 24, 2048.
8. Eda, M., Ashimori, A., Akahoshi, F., Yoshimura, T., Inoue, Y., Fukaya, C., Nakajima, M., Fukuyama, H., Imada, T. and Nakamura, N. (1998) Bioorg. Med. Chem. Lett. 8, 913.
9. Fukami, H., Okunishi, H. and Miyazaki, M. (1998) Curr. Pharm. Design. 4, 439.
10. Niwata, S., Fukami, H., Sumida, M., Ito, A., Kakutami, S., Saitoh, M., Suzuki, K., Imoto, M., Shibata, H., Imajo, S., Kiso, Y., Tanaka, T., Nakazato, H., Ishihara, T., Takai, S., Yamamoto, D., Shiota, N., Miyazato, M., Okunishi, H., Kinoshita, A., Urata, H. and Arakawa, K. (1997) J. Med. Chem. 40, 2156.
11. Alagille, D., Pfeiffer, B., Scalbert, E., Ferry G., Boutin, J.A., Renard, P., Viaud-Massuard, M.C. Eur. J. Med. Chem. Submitted for publication.
12. Maume, D., Lancelot, J.C. and Rabbat, M. (1979) J. Hetero. Chem. 20, 1217.
13. O'Connell, J.F. and Rapoport, H. (1992) J. Org. Chem. 57, 4775.
14. Ferry, G., Gillet, L., Bruneau, V., Banales, J., Beauverger, P., Coge, F., Galizzi, J.P., Scalbert, E., Okamoto, T., Urata, H. and Boutin, J.A. (2001) Eur. J. Biochem. 268, 5885.