4-heterocyclohexanone-based inhibitors of the serine protease plasmin

Journal of Medicinal Chemistry

Volumn 42, Issue 15, 1999, Pages 2969-2976

  Sanders, Tanya C ^a   Seto, Christopher T ^a  

^a BROWN UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ANTIPLASMIN; CYCLOHEXANONE DERIVATIVE; KALLIKREIN; SERINE PROTEINASE INHIBITOR; THROMBIN; TRYPSIN;

ANGIOGENESIS; ANTINEOPLASTIC ACTIVITY; ARTICLE; CONTROLLED STUDY; DRUG DESIGN; DRUG SELECTIVITY; DRUG SYNTHESIS; METASTASIS INHIBITION;

BINDING SITES; CYCLOHEXANES; PLASMIN; SERINE PROTEINASE INHIBITORS; STRUCTURE-ACTIVITY RELATIONSHIP;

EID: 0033614992     PISSN: 00222623     EISSN: None     Source Type: Journal    
DOI: 10.1021/jm990110k     Document Type: Article

References (22)

1. Cao, Y.; O'Reilly, M. S.; Marshall, B.; Flynn, E.; Ji, R.; Folkman, J. Expression of Angiostatin cDNA in Murine Fibrosarcoma Suppresses Primary Tumor Growth and Produces Long-Term Dormancy of Metastases. J. Clin. Invest. 1998, 101, 1055.
2. Wu, Z.; O'Reilly, M. S.; Folkman, J.; Shing, Y. Suppression of Tumor Growth With Recombinant Murine Angiostatin. Biochem. Biophys. Res. Commun. 1997, 236, 651.
3. Pepper, J. S.; Montesano, R.; Mandriots, S. J.; Orci, L.; Vassalli, J. Angiogenesis: A Paradigm for Balanced Extracellular Proteolysis During Cell Migration and Morphogenesis. Enzyme Protein 1996, 49, 138.
4. Liotta, L. A. Cancer Cell Invasion and Metastasis. Sci. Am. 1992, February, 54.
5. Sherry, S. Fibrinolysis, Thrombosis, and Hemostasis; Lea & Febiger: Philadelphia, PA, 1992; Chapter 1.
6. Okada, Y.; Tsuda, Y.; Teno, N.; Wanaka, K.; Bohgaki, M.; Hijikata-Okunomiya, A.; Naito, T.; Okamoto, S. Synthesis of Active Center-Directed Peptide Inhibitors of Plasmin. Chem Pharm. Bull. 1988, 36, 1289.
7. Ganu, V. S.; Shaw, E. Improved Synthetic Inactivators of Plasmin. Thromb. Res. 1987, 45, 1.
8. 3 Bicyclic Lactam Moiety. Bioorg. Med. Chem. Lett. 1997, 7, 331; and refs 6 and 16.
9. 3 Bicyclic Lactam Moiety. Bioorg. Med. Chem. Lett. 1997, 7, 331; and refs 6 and 16.
10. 3 Bicyclic Lactam Moiety. Bioorg. Med. Chem. Lett. 1997, 7, 331; and refs 6 and 16.
11. Conroy, J. L.; Sanders, T. C.; Seto, C. T. Using the Electrostatic Field Effect to Design a New Class of Inhibitors for Cysteine Proteases. J. Am. Chem. Soc. 1997, 119, 4285.
12. 13C NMR Studies that Tetrahydropyranone-Based Inhibitors Bind to Cysteine Proteases by Reversible Formation of a Hemithioketal Adduct. J. Org. Chem. 1998, 63, 2367.
13. Brady, K.; Abeles, R. H. Inhibition of Chymotrypsin by Peptidyl Trifluoromethyl Ketones: Determinants of Slow-Binding Kinetics. Biochemistry 1990, 29, 7608.
14. Smith, R. A.; Copp, L. J.; Donnelly, S. L.; Spencer, R. W.; Krantz, A. Inhibition of Cathepsin B by Peptidyl Aldehydes and Ketones: Slow-Binding Behavior of a Trifluoromethyl Ketone. Biochemistry 1988, 27, 6568.
15. Otto, H.-H.; Schirmeister, T. Cysteine Proteases and Their Inhibitors. Chem. Rev. 1997, 97, 133.
16. Simon, R. J.; Kania, R. S.; Zuchermann, R. N.; Huebner, V. D.; Jewell, D. A.; Banville, S.; Ng, S.; Wang, L.; Rosenberg, S. Peptoids: A Modular Approach to Drug Discovery. Proc. Natl. Acad. Sci. U.S.A. 1992, 89, 9367.
17. Matsuzaki, T.; Sasaki, C.; Umeyama, H. A Predicted Tertiary Structure of a Thrombin Inhibitor-Trypsin Complex Explains the Mechanisms of the Selective Inhibition of Thrombin, Factor Xa, Plasmin, and Trypsin. J. Biochem. 1988, 103, 537.
18. Teno, N.; Wanaka, K.; Okada, Y.; Tsuda, Y.; Okamoto, U.; Hijikata-Okunomiya, A.; Naito, T.; Okamoto, S. Development of Active Center-Directed Inhibitors Against Plasmin. Chem. Pharm. Bull. 1991, 39, 2340.
19. Abdel-Magid, A. F.; Carson, K. G.; Harris, B. D.; Maryanoff, C. A.; Shah, R. D. Reductive Amination of Aldehydes and Ketones with Sodium Triacetoxyborohydride. Studies in Direct and Indirect Reductive Amination Procedures. J. Org. Chem. 1996, 61, 3849.
20. Carpino, L. A.; Sadat-Aalace, D.; Chao, H. G.; DeSelms, R. H. ((9-Fluorenylmethyl)oxy)carbonyl (Fmoc) Amino Acid Fluorides. Convenient New Peptide Coupling Reagents Applicable to the Fmoc/tert-Butyl Strategy for Solution and Solid-Phase Synthesis. J. Am. Chem. Soc. 1890, 112, 9651.
21. Kamphuis, I. G.; Kalk, K. H.; Swarte, M. B. A.; Drenth, J. Structure of Papain Refined at 1.65 Å Resolution. J. Mol. Biol. 1984, 179, 233.
22. Hitomi, Y.; Ikari, N.; Fujii, S. Inhibitory Effect of a New Synthetic Protease Inhibitor (FUT-175) on the Coagulation System. Haemostasis 1985, 15, 164.