Novel 3-carboxamide-coumarins as potent and selective FXIIa inhibitors

Journal of Medicinal Chemistry

Volumn 51, Issue 11, 2008, Pages 3077-3080

  Robert, Séverine ^a   Bertolla, Carine ^a   Masereel, Bernard ^a   Dogné, Jean Michel ^a   Pochet, Lionel ^a  

^a UNIVERSITY OF NAMUR   (Belgium)

Author keywords

[No Author keywords available]

Indexed keywords

BLOOD CLOTTING FACTOR 10A; BLOOD CLOTTING FACTOR 12A; BLOOD CLOTTING FACTOR 7A; COUMARIN DERIVATIVE; KALLIKREIN; THROMBIN;

ARTICLE; CHEMICAL REACTION; DRUG ACTIVITY; DRUG POTENCY; DRUG STRUCTURE; DRUG SYNTHESIS; DRUG TARGETING; HUMAN;

AMIDES; ANTICOAGULANTS; COUMARINS; FACTOR XIIA; STRUCTURE-ACTIVITY RELATIONSHIP;

EID: 44949161937     PISSN: 00222623     EISSN: None     Source Type: Journal    
DOI: 10.1021/jm8002697     Document Type: Article

References (27)

1. Gailani, D.; Renne, T. Intrinsic pathway of coagulation and arterial thrombosis. Arterioscler Thromb Vasc Biol 2007, 27, 2507-2513.
2. Hoffman, M.; Monroe, D. M. A cell-based model of hemostasis. Thromb Haemostasis 2001, 85, 958-965.
3. Ratnoff, O. D.; Colopy, J. E. A familial hemorrhagic trait associated with a deficiency of a clot-promoting fraction of plasma. J. Clin. Invest. 1955, 34, 602-613.
4. Renne, T.; Nieswandt, B.; Gailani, D. The intrinsic pathway of coagulation is essential for thrombus stability in mice. Blood Cells, Mol. Dis. 2006, 36, 148-151.
5. Renne, T.; Gailani, D. Role of factor XII in hemostasis and thrombosis: clinical implications. Expert Rev. Cardiovasc. Ther. 2007, 5, 733-741.
6. Renne, T.; Pozgajova, M.; Gruner, S.; Schuh, K.; Pauer, H. U.; Burfeind, P.; Gailani, D.; Nieswandt, B. Defective thrombus formation in mice lacking coagulation factor XII. J. Exp. Med. 2005, 202, 271-281.
7. Kleinschnitz, C.; Stoll, G.; Bendszus, M.; Schuh, K.; Pauer, H. U.; Burfeind, P.; Renne, C.; Gailani, D.; Nieswandt, B.; Renne, T. Targeting coagulation factor XII provides protection from pathological thrombosis in cerebral ischemia without interfering with hemostasis. J. Exp. Med. 2006, 203, 513-518.
8. Silverberg, M.; Kaplan, A. P. Enzymatic activities of activated and zymogen forms of human Hageman factor (factor XII). Blood 1982, 60, 64-70.
9. Pauer, H. U.; Renne, T.; Hemmerlein, B.; Legler, T.; Fritzlar, S.; Adham, I.; Muller-Esterl, W.; Emons, G.; Sancken, U.; Engel, W.; Burfeind, P. Targeted deletion of murine coagulation factor XII gene-a model for contact phase activation in vivo. Thromb. Haemostasis 2004, 92, 503-508.
10. Gailani, D.; Renne, T. The intrinsic pathway of coagulation: a target for treating thromboembolic disease. J. Thromb. Haemostasis 2007, 5, 1106-1112.
11. Carter, T. H.; Everson, B. A.; Ratnoff, O. D. Cabbage seed protease inhibitor: a slow, tight-binding inhibitor of trypsin with activity toward thrombin, activated Stuart factor (factor Xa), activated Hageman factor (factor XIIa), and plasmin. Blood 1990, 75, 108-115.
12. Cruz-Silva, I.; Gozzo, A. J.; Nunes, V. A.; Carmona, A. K.; Faljoni-Alario, A.; Oliva, M. L.; Sampaio, M. U.; Sampaio, C. A.; Araujo, M. S. A proteinase inhibitor from Caesalpinia echinata (pau-brasil) seeds for plasma kallikrein, plasmin and factor XIIa. Biol. Chem. 2004, 385, 1083-1086.
13. Hayashi, K.; Takehisa, T.; Hamato, N.; Takano, R.; Hara, S.; Miyata, T.; Kato, H. Inhibition of serine proteases of the blood coagulation system by squash family protease inhibitors. J. Biochem. 1994, 116, 1013-1018.
14. Hojima, Y.; Pierce, J. V.; Pisano, J. J. Pumpkin seed inhibitor of human factor XIIa (activated Hageman factor) and bovine trypsin. Biochemistry 1982, 21, 3741-3746.
15. Krishnamoorthi, R.; Gong, Y. X.; Richardson, M. A new protein inhibitor of trypsin and activated Hageman factor from pumpkin (Cucurbita maxima) seeds. FEBS Lett. 1990, 273, 163-167.
16. Sampaio, C. A.; Oliva, M. L.; Tanaka, A. S.; Sampaio, M. U. Proteinase inhibitors in Brazilian Leguminosae. Mem. Inst. Oswaldo Cruz 1991, 86 (Suppl. 2), 207-209.
17. Sampaio, C. A.; Motta, G.; Sampaio, M. U.; Oliva, M. L.; Araujo, M. S.; Stella, R. C.; Tanaka, A. S.; Batista, I. F. Action of plant proteinase inhibitors on enzymes of the kallikrein kinin system. Agents Actions Suppl. 1992, 36, 191-199.
18. Campos, I. T.; Tanaka-Azevedo, A. M.; Tanaka, A. S. Identification and characterization of a novel factor XIIa inhibitor in the hematophagous insect, Triatoma infestans (Hemiptera: Reduviidae). FEBS Lett. 2004, 577, 512-516.
19. Campos, I. T.; Amino, R.; Sampaio, C. A.; Auerswald, E. A.; Friedrich, T.; Lemaire, H. G.; Schenkman, S.; Tanaka, A. S. Infestin, a thrombin inhibitor presents in Triatoma infestans midgut, a Chagas' disease vector: gene cloning, expression and characterization of the inhibitor. Insect Biochem. Mol. Biol. 2002, 32, 991-997.
20. Foster, C. B.; Flanigan, T. P.; DeStigter, K. K.; Blanton, R.; Dumenco, L. L.; Gallagher, C.; Ratnoff, O. D. Inhibition of the activation of Hageman factor (factor XII) by extracts of Schistosoma mansoni. J. Lab. Clin. Med. 1992, 120, 735-739.
21. Ulmer, J. S.; Lindquist, R. N.; Dennis, M. S.; Lazarus, R. A. Ecotin is a potent inhibitor of the contact system proteases factor XIIa and plasma kallikrein. FEBS Lett. 1995, 365, 159-163.
22. Frederick, R.; Robert, S.; Charlier, C.; de Ruyck, J.; Wouters, J.; Pirotte, B.; Masereel, B.; Pochet, L. 3,6-Disubstituted coumarins as mechanism-based inhibitors of thrombin and factor Xa. J. Med. Chem. 2005, 48, 7592-7603.
23. Bogdal, D. Coumarins: fast synthesis by Knoevenagel condensation under microwave irradiation. J. Chem. Res. (S) 1998, 468-469.
24. Montalbetti, C. A. G. N.; Falque, V. Amide bond formation and peptide coupling. Tetrahedron 2005, 61, 10827-10852.
25. 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. Esters and amides of 6-(chloromethyl)-2-oxo-2H-1-benzopyran-3-carboxylic acid as inhibitors of alpha-chymotrypsin: significance of the "aromatic" nature of the novel ester-type coumarin for strong inhibitory activity. J. Med. Chem. 1996, 39, 2579-2585.
26. Pochet, L.; Doucet, C.; Dive, G.; Wouters, J.; Masereel, B.; Reboud-Ravaux, M.; Pirotte, B. Coumarinic derivatives as mechanism-based inhibitors of alpha-chymotrypsin and human leukocyte elastase. Bioorg. Med. Chem. 2000, 8, 1489-1501.
27. Pochet, L.; Dieu, M.; Frédérick, R.; Murray, A. M.; Kempen, I.; Pirotte, B.; Masereel, B. Investigation of the inhibition mechanism of coumarins on chymotrypsin by mass spectrometry. Tetrahedron 2003, 59, 4557-4561.