Targeting thrombin and factor VIIa: Design, synthesis, and inhibitory activity of functionally relevant indolizidinones

Bioorganic and Medicinal Chemistry Letters

Volumn 12, Issue 20, 2002, Pages 2907-2911

  Hanessian, Stephen ^a   Therrien, Eric ^a   Granberg, Kenneth ^b   Nilsson, Ingemar ^b  

^a UNIVERSITÉ DE MONTRÉAL   (Canada)

^b ASTRAZENECA R AND D   (Sweden)

Author keywords

[No Author keywords available]

Indexed keywords

BLOOD CLOTTING FACTOR 7A; BLOOD CLOTTING FACTOR 7A INHIBITOR; INDOLIZIDINE DERIVATIVE; THROMBIN; THROMBIN INHIBITOR; UNCLASSIFIED DRUG;

ARTICLE; CRYSTAL STRUCTURE; DRUG ACTIVITY; DRUG DESIGN; DRUG SYNTHESIS; MOLECULAR MODEL; X RAY CRYSTALLOGRAPHY;

CRYSTALLOGRAPHY, X-RAY; DRUG DESIGN; FACTOR VIIA; HUMANS; INDOLIZINES; MODELS, MOLECULAR; MOLECULAR CONFORMATION; PLASMIN; SPECTROMETRY, MASS, ELECTROSPRAY IONIZATION; STRUCTURE-ACTIVITY RELATIONSHIP; THROMBIN;

EID: 0037152493     PISSN: 0960894X     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0960-894X(02)00612-1     Document Type: Article

References (33)

1. (a) Bode, W.; Huber, R.; Rydel, T. J.; Tulinsky, A. Thrombin: Structure and Function; Berliner, L. J. Ed., Plenum, New York, 1992, p 3.
2. (b) Agnelli, G.; Pascucchi, C.; Cosmi, B.; Nenci, G.G. Thromb. Haemostasis 1991, 66, 592.
3. © Colman, R. W.; Marder, V. J.; Salzman, E. Hirsch, W.; in Hemostasis and Thrombosis: Basic Principle and Clinical Practice, 3rd ed.; Colman, R. W., Hirsch, W., Marder, V. J., Salzman, E. W., Eds.; J. B. Lippincott; Philadelphia, 1994: p 3.
4. (a) Steinmetzer T., Hauptmann J., Stürzebecher J. Exp. Opin. Invest. Drugs. 10:2001;845.
5. (b) Sanderson P.E.J., Naylor-Olsen A.M. Curr. Med. Chem. 5:1998;289.
6. © Ripka W.C. Curr. Opin. Chem. Biol. 1:1997;242.
7. Current treatment involves intravenous administration of heparin or oral dosage of Warfarin.
8. (a) Kalafatis M., Egan J.O., van't Veer C., Cawthern K., Mann K.G. Curr. Rev. Eukaryotic Gene Expression. 7:1997;241.
9. (b) Bouma B.N., von dem Borne P.A.K., Meijers J.C.M. Thromb. Haemost. 80:1998;24.
10. © Mann K.G. Thromb. Haemost. 82:1999;165.
11. (a) Banner D.W., D'Arcy A., Chene C., Winkler F.K., Guha A., Konigsberg W.H., Nemerson Y., Kirchhofer D. Nature. 380:1996;41.
12. (b) Kirchhofer D., Banner D.W. Trends Cardiovasc. Med. 7:1997;316.
13. (a) See for example, Roussel P., Bradley M., Kane P., Bailey C., Arnold R., Cross A. Tetrahedron. 55:1999;6219
14. (b) Kohrt J.T., Filipski K.J., Rapundalo S.T., Cody W.L., Edmunds J.J. Tetrahedron Lett. 41:2000;6041.
15. © Dennis M.S., Eigenbrot C., Skelton N.J., Ultsch M.H., Santell L., Dwyer M.A., O'Connell M.P., Lazarus R.A. Nature. 404:2000;465.
16. (a) PPACK II dihydrochloride is commercially available from CALBIO, CAS# 74392-49-7.
17. Wiley, M.R.; Chirgadze, N.Y.; Clawson, D.K.; Craft, T.J.; Gifford-Moore, D.S.; Jones, N.D.; Olkowski, J.L.; Weir, L.C.; Smith, G.F. Bioorg. Med. Chem. Lett. 1996, 6, 2387.
18. Hanessian S., Balaux E., Musil D., Olsson L.-L., Nilsson I. Bioorg. Med. Chem. Lett. 10:2000;243.
19. (a) The GOLD docking program see, Jones G., Willett P., Glen R.C. J. Mol. Biol. 245:1995;43.
20. (b) Jones G., Willett P., Glen R.C. J. Comput. Aid. Mol. Des. 9:1995;532.
21. © Jones G., Willett P., Glen R.C., Leach A.R., Taylor R. J. Mol. Biol. 267:1997;727.
22. (a) Hanessian S., McNaughton-Smith G. Bioorg. Med. Chem. Lett. 6:1996;1567.
23. (b) Hanessian S., Ronan B., Laoui A. Bioorg. Med. Chem. Lett. 4:1994;1397.
24. © Silverman R.B., Levy M.A. J. Org. Chem. 45:1980;815.
25. Speckamp W.N., Hiemstra H. Tetrahedron. 41:1985;4367.
26. (a) Casiraghi G., Rassu G. Synthesis. 1995;607.
27. (b) Casiraghi G., Zanardi F., Appendino G., Rassu G. Chem. Rev. 100:2000;1929.
28. Boeckman R.K. Jr., Potenza J.C. Tetrahedron Lett. 26:1985;1411.
29. (a) Evans D.A., Britton T.C., Ellman J.A., Dorow R.L. J. Am. Chem. Soc. 112:1990;4011
30. (b) Hanessian S., Wang W., Gai Y. Tetrahedron Lett. 37:1996;7477.
31. © Wasserman H.H., Hlasta D.J. J. Am. Chem. Soc. 100:1978;6780.
32. (d) Kuhlein K., Jensen H. Justus Liebigs Ann. Chem. 369:1974;. and references cited therein.
33. Bayley H., Standring D.N., Knowles J.R. Tetrahedron Lett. 19:1978;3633.