Esters and amides of 6-(chloromethyl)-2-oxo-2H-1-benzopyran-3-carboxylic acid as inhibitors of a-chymotrypsin: significance of the ‘aromatic’ nature of the novel ester-type coumarin for strong inhibitory activity
Pochet, L.; Doucet, C.; Schynts, M.et al.
1996 • In Journal of Medicinal Chemistry, 39, p. 2579-2585
Pirotte, Bernard ; Université de Liège - ULiège > Département de pharmacie > Chimie pharmaceutique
Jiang, K. Y.
Masereel, B.
De Tullio, Pascal ; Université de Liège - ULiège > Département de pharmacie > Chimie pharmaceutique
Delarge, J.
Reboud-Ravaux, M.
Language :
English
Title :
Esters and amides of 6-(chloromethyl)-2-oxo-2H-1-benzopyran-3-carboxylic acid as inhibitors of a-chymotrypsin: significance of the ‘aromatic’ nature of the novel ester-type coumarin for strong inhibitory activity
Publication date :
1996
Journal title :
Journal of Medicinal Chemistry
ISSN :
0022-2623
eISSN :
1520-4804
Publisher :
American Chemical Society, Washington, United States - District of Columbia
Powers, J. C.; Zimmerman, M. Inhibitors of Elastases, Chymases and Cathepsin G. In Design of Enzyme Inhibitors as Drugs; Sandler, M., Smith, H. J., Eds.; Oxford University Press: Oxford, 1989; pp 596-619.
Demuth, H.-U. Recent Developments in Inhibiting Cysteine and Serine Proteases. J. Enzyme Inhib. 1990, 3, 249-278.
Rivett, A. J. Proteasomes: Multicatalytic Proteinase Complexes. Biochem. J. 1993, 291, 1-10.
Hlasta, D. J.; Pagani, E. D. Human Leukocyte Elastase Inhibitors. Annu. Rep. Med. Chem. 1994, 29, 195-204.
Bernstein, P. R.; Edwards, P. D.; Williams, J. C. Inhibitors of Human Leukocyte Elastase. In Progress in Medicinal Chemistry, Vol. 31; Ellis, G. P., Luscombe, D. K., Eds.; Elsevier: New York, 1994; pp 59-120.
Silverman, R. B. Mechanism-based Enzyme Inactivation: Chemistry and Enzymology; CRC Press: Boca Raton, FL, 1988; Vol. 1, pp 95-156.
Daniels, S. B.; Cooney, E.; Sofia, M. J.; Chakravarty, P. K.; Katzenellenbogen, J. A. Haloenol Lactones: Potent Enzyme-Activated Irreversible Inhibitors for α-Chymotrypsin. J. Biol. Chem. 1983, 258, 15046-15053.
Katzenellenbogen, J. A.; Rai, R.; Dai, W. Enol Lactone Derivatives as Inhibitors of Human Neutrophil Elastase and Trypsin-like Proteases. Bioorg. Med. Chem. Lett. 1992, 2, 1399-1404.
Tam, T. F.; Spencer, R. W.; Thomas, E. M.; Copp, L. J.; Krantz, A. Novel Suicide Inhibitors of Serine Proteinases. Inactivation of Human Leukocyte Elastase by Ynenol Lactones. J. Am. Chem. Soc. 1984, 106, 6849-6851.
Harper, J. W.; Hemmi, K.; Powers, J. C. Reaction of Serine Proteases with Substituted Isocoumarins. Discovery of 3, 4-Dichloroisocoumarin, a new general Mechanism Based Serine Protease Inhibitor. Biochemistry 1985, 24, 1831-1841.
Harper, J. W.; Powers, J. C. Reaction of Serine Proteases with Substituted 3-Alkoxy-4-chloroisocoumarins and 3-Alkoxy-7-amino-4-chloroisocoumarins. New Reactive Mechanism Based Inhibitors. Biochemistry 1985, 24, 7200-7213.
Béchet, J.-J.; Dupaix, A.; Yon, J.; Wakselman, M.; Robert, J.-L.; Vilkas, M. Inactivation of α-Chymotrypsin by a Bifunctional Reagent, 3, 4-Dihydro-3, 4-dibromo-6-bromo-methylcoumarin. Eur. J. Biochem. 1973, 35, 527-539.
Mor, A.; Maillard, J.; Favreau, C.; Reboud-Ravaux, M. Reaction of Thrombin and Proteinases of the Fibrinolytic System with a Mechanism-Based Inhibitor, 3, 4-Dihydro-3-benzyl-6-chloromethylcoumarin. Biochim. Biophys. Acta 1990, 1038, 119-124.
Wakselman, M.; Xie, J.; Mazaleyrat, J.-P.; Boggetto, N.; Vilain, A.-C.; Montagne, J.-J.; Reboud-Ravaux, M. New Mechanism-Based Inactivators of Trypsin-like Proteinases. Selective Inactivation of Urokinase by Functionalized Cyclopeptides Incorporating a Sulfoniomethyl-Substituted m-Aminobenzoic Acid Residue. J. Med. Chem. 1993, 36, 1539-1547.
Doherty, J. B.; Ashe, B. M.; Argenbright, L. W.; Barker, P. L.; Bonney, R. J.; Chandler, G. O.; Dahlgren, M. E.; Dorn, C. P., Jr.; Finke, P. E.; Firestone, R. A.; Fletcher, D.; Hagmann, W. K.; Mumford, R.; O'Grady, L.; Maycock, A. L.; Pisano, J. M.; Shah, S. K.; Thompson, K. R.; Zimmerman, M. Cephalosporin Antibiotics can be Modified to Inhibit Human Leucocyte Elastase. Nature 1986, 322, 192-194.
Knight, W. B.; Green, B. G.; Chablin, 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.; Liesch, J.; MacCoss, M.; Navia, M. A.; Shah, S. K.; Underwood, D.; Doherty, J.B. Specificity, Stability and Potency of Monocyclic β-Lactam Inhibitors of Human Leucocyte Elastase. Biochemistry 1992, 31, 8160-8170.
Maillard, J.-L.; Favreau, C.; Reboud-Ravaux, M.; Kobaiter, R.; Joyau, R.; Wakselman, M. Biological Evaluation of the Inhibition of Neutrophil Elastase by a Synthetic β-Lactam Derivative. Eur. J. Biol. 1990, 52, 213-221.
Wakselman, M.; Joyau, R.; Kobaiter, R.; Boggetto, N.; Vergely, I.; Maillard, J.; Okochi, V.; Montagne, J. J.; Reboud-Ravaux, M. Functionalized N-Arylazetidinones as Novel Mechanism-Based Inhibitors of Neutrophil Elastase. FEBS Lett. 1991, 282, 377-381.
Béchet, J.-J.; Dupaix, A.; Blagoeva, I. Inactivation of α-Chymotrypsin by New Bifunctional Reagents: Halomethylated Derivatives of Dihydrocoumarins. Biochimie 1977, 59, 231-239.
Béchet, J.-J.; Dupaix, A.; Roucous, C.; Bonamy, A.-M. Inactivation of Proteases and Esterases by Halomethylated Derivatives of Dihydrocoumarins. Biochimie 1977, 59, 241-246.
Vilain, A.-C.; Okochi, V.; Vergely, I.; Reboud-Ravaux, M.; Mazaleyrat, J.-P.; Wakselman, M. Acyloxybenzyl Halides, Inhibitors of Elastases. Biochim. Biophys. Acta 1991, 119-127.
Reboud-Ravaux, M.; Desvages, G. Inactivation of Human High-and Low-Molecular-Weight Urokinases. Analysis of their Active Site. Biochim. Biophys. Acta 1984, 791, 333-341.
Wakselman, M. 1,4- and 1,6-Eliminations from Hydroxy- and Amino-Substituted benzyl Systems: Chemical and Biochemical Application. Nouv. J. Chimie 1983, 7, 439-447.
Stoermer, R.; Behn, K. Synthese Aromatischer Alkohole mit Formaldehyd. Ber. 1901, 34, 2455-2460.
Horning, E. C.; Horning, M. G.; Dimmig, D. A. 3-Carbethoxycoumarin. Organic Syntheses Coll. Vol. 3 1955, 165-167.
Reichert, B.; Hoss, W. Uber den 2-Oxy-5-chloromethyl-benzaldehyd. Ber. 1942, 75, 157-171.
