Coumarinic derivatives as mechanism-based inhibitors of α-chymotrypsin and human leukocyte elastase

Bioorganic and Medicinal Chemistry

Volumn 8, Issue 6, 2000, Pages 1489-1501

  Pochet, Lionel ^a   Doucet, Caroline ^b   Dive, Georges ^c   Wouters, Johan ^a   Masereel, Bernard ^a   Reboud Ravaux, Michèle ^b   Pirotte, Bernard ^c  

^a UNIVERSITY OF NAMUR   (Belgium)

^b Dept Biol Supramoleculaire C   (France)

^c UNIVERSITY OF LIÈGE   (Belgium)

Author keywords

[No Author keywords available]

Indexed keywords

CHYMOTRYPSIN A; COUMARIN DERIVATIVE; ELASTASE; ELASTASE INHIBITOR; ENZYME INHIBITOR; KETONE DERIVATIVE; THIOESTER;

ARTICLE; CHEMICAL REACTION KINETICS; ENZYME INHIBITION; NONHUMAN;

CHYMOTRYPSIN; COUMARINS; CRYSTALLOGRAPHY, X-RAY; ENZYME INHIBITORS; HUMANS; LEUKOCYTE ELASTASE; MAGNETIC RESONANCE SPECTROSCOPY; SPECTROPHOTOMETRY, INFRARED;

EID: 0034095633     PISSN: 09680896     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0968-0896(00)00071-7     Document Type: Article

References (42)

1. Powers, J. C.; Zimmerman, M. In Design of Enzyme Inhibitors as Drugs; Sandler, M., Smith, H. J., Eds.; Oxford University Press: Oxford, 1989; pp 596-619.
2. Powers, J. C.; Harper, J. W. In Proteinase Inhibitors; Barett, A. J., Salvensen, G., Eds.; Elsevier: Amsterdam, 1986; pp 55-152.
3. Hlasta D.J., Pagani E.D. Ann. Rep. Med. Chem. 29:1994;195.
4. Janoff A. Am. Rev. Respir. Dis. 132:1985;417.
5. Demling R.H. Annu. Rev. Med. 46:1995;193.
6. Janoff A. Annu. Rev. Med. 36:1985;207.
7. Snider G.L. Drug. Dev. Res. 10:1987;235.
8. Nadel J.A. Am. Rev. Respir. Dis. 14:1991;S48.
9. Rai R., Katzenellenbogen J.A. J. Med. Chem. 35:1992;4297.
10. Rai R., Katzenellenbogen J.A. J. Med. Chem. 35:1992;4150.
11. Katzenellenbogen J.A., Rai R., Dai W. Bioorg. Med. Chem. Lett. 2:1992;1399.
12. Alpegiani, M.; Bissolino, P.; Corigli, R.; Del-Nero, S.; Perrone, E.; Rizzo, V.; Sacchi, N.; Cassinelli, G.; Franceschi, G.; Baici, J. Med. Chem. 1994, 37, 4003.
13. Finke P.E., Ashe B.M., Knight W.B., Maycock A.L., Navia M.A., Shah S.K., Thompson K.R., Underwood D.J., Weston H., Zimmerman M., Doherty J.B. J. Med. Chem. 33:1990;2522.
14. Finke P.E., Shah S.K., Fletcher D.S., Ashe B.M., Brause K.A., Chandler G.O., Dellea P.S., Hand K.M., Maycock A.L., Osinga D.G., Underwood D.J., Weston H., Davies P. J. Med. Chem. 38:1995;2449.
15. Knight W.B., Green B.G., Chabin R.M., Gale P., Maycock A.L., Weston H., Kuo D.W., Westler W.M., Dorn C.P., Finke P.E., Hagmann W.K., Hale J.J., Liesh J., MacCoss M., Navia M.A., Shah S.K., Underwood D., Doherty J.B. Biochemistry. 31:1992;8160.
16. Wakselman M., Joyeau R., Kobaiter R., Bogetto N., Vergely I., Maillard J., Okochi V., Montagne J.J., Reboud-Ravaux M. FEBS Lett. 282:1991;377.
17. Groutas W.C., Houser-Archield N., Chong L.S., Venkataraman R., Epp J.B., Huang H., McClenahan J.J. J. Med. Chem. 36:1993;3178.
18. Desai R.C., Court J.C., Ferguson E., Gordon R.J., Hlasta D.J., Dunlap R.P., Franke C.A. J. Med. Chem. 38:1995;1571.
19. Krantz A., Spencer R.W., Tam T.F., Liak T.J., Copp L.J., Thomas E.M., Rafferty S.P. J. Med. Chem. 33:1990;464.
20. Uejima Y., Kokubo M., Oshida J., Kawabata H., Kato Y., Fujii K. Pharmacol. Exp. Ther. 265:1993;516.
21. Hernandez M.A., Powers J.C., Glinski J., Oleksyszyn J., Vijayalakshmi J., Meyer E.F. Jr. J. Med. Chem. 35:1992;1121.
22. Kam C.M., Kerrigan J.E., Plaskon R.R., Duffy E.J., Lollar P., Suddath F.L., Powers J.C. J. Med. Chem. 37:1994;1298.
23. Kerrigan J.E., Oleksyszyn J., Kam C.M., Selzler J., Powers J.C. J. Med. Chem. 38:1995;544.
24. Béchet J.-J., Dupaix A., Yon J., Wakselman M., Robert J.-L., Vilkas M. Eur. J. Biochem. 35:1973;527.
25. Mor A., Maillard J., Favreau C., Reboud-Ravaux M. Biochim. Biophys. Acta. 1038:1990;119.
26. Groutas W.C., Kuang R., Venkataraman R. Biochem. Biophys. Res. Commun. 198:1994;341.
27. Groutas W.C., Kuang R., Venkataraman R., Epp J.B., Ruan S., Prakash O. Biochemistry. 36:1997;4739.
28. Pochet L., Doucet C., Schynts M., Thierry N., Boggetto N., Pirotte B., Jiang K.-Y., Masereel B., de Tullio P., Delarge J., Reboud-Ravaux M. J. Med. Chem. 39:1996;2579.
29. Wakselman M. Nouv. J. Chim. 7:1983;439.
30. Dive G., Dehareng D., Peeters D. Int. J. Quant. Chem. 58:1996;85.
31. Boggetto N., Vilain A.C., Montagne J.J., Reboud-Ravaux M., Mazaleyrat J.P., Xie J., Wakselman M. Bull. Soc. Chim. Fr. 131:1994;152.
32. Joyeau R., Felk A., Guilaume S., Wakselman M., Vergely I., Doucet C., Boggetto N., Reboud-Ravaux M. J. Pharm. Pharmacol. 48:1996;1218.
33. Doucet C., Vergely I., Reboud-Ravaux M., Guilhem J., Kobaiter R., Joyeau R., Wakselman M. Tetrahedron: Asymmetry. 8:1997;739.
34. Doucet C., Pochet L., Thierry N., Pirotte B., Delarge J., Reboud-Ravaux M. J. Med. Chem. 42:1999;4161.
35. -1, respectively. See ref 28.
36. Bowden, J.; Hanson, M. J.; Taylor, G. R. J. Chem. Soc. 1968, 174.
37. Lippold B.C., Garett E.R. J. Pharm. Sci. 60:1971;1019.
38. Wakselman M., Xie J., Mazaleyrat J.-P., Bogetto N., Vilain A.-C., Montagne J.-J., Reboud-Ravaux M. J. Med. Chem. 36:1993;1539.
39. Silverman, R. B. In Mechanism-Based Enzyme Inactivation: Chemistry and Enzymology; CRC Press: Boca Raton, FL, 1988; Vol. 1, pp 22-23.
40. Tatewaki H., Huzinaga S. J. Comp. Chem. 1:1980;205.
41. Dive G., Dehareng D., Ghuysen J.M. Theoret. Chim. Acta. 85:1993;409.
42. Frisch, M. J.; Trucks, G. W.; Schlegel, H. B.;Gill, P. M. W.; Johnson, B. G.; Robb, M. A.; Cheeseman, J. R.; Keith, T.; Petersson, G. A.; Montgomery, J. A.; Raghavachari, K.; Al-Laham, M. A.; Zakrzewski, V. G.; Ortiz, J. V.; Foresman, J. B.; Cioslowski, J.; Stefanov, B. B.; Nanayakkara, A.; Challacombe, M.; Peng, C. Y.; Ayala, P. Y.; Chen, W.; Wong, M. W.; Andres, J. L.; Replogle, E. S.; Gomperts, R.; Martin, R. L.; Fox, D. J.; Binkley, J. S.; Defrees, D. J.; Baker, J.; Stewart, J. P.; Head-Gordon, M.; Gonzalez, C.; Pople, J. A. Gaussian 94, Revision D.4; Pittsburgh, PA, 1995.