Synthesis and evaluation of 3-substituted-4-oxa-azabicyclo [3,2,0]heptan-7-ones as cynteine proteases inhibitors: Part II

Arkivoc

Volumn 2001, Issue 6, 2001, Pages 116-121

  Zhou, Nian E ^a   Reddy, Andhe V N ^a   Kaleta, Jadwiga ^a   Micetich, Ronald G ^a   Singh, Rajeshwar ^a  

^a NAEJA Pharmaceutical Inc   (Canada)

Author keywords

Lactams; 3 Substituted oxapenam; Cysteine protease inhibitor

Indexed keywords

CYSTEINE PROTEINASE; CYSTEINE PROTEINASE INHIBITOR; KETONE DERIVATIVE; PAPAIN;

ARTICLE; CHEMICAL MODIFICATION; DRUG ACTIVITY; DRUG DESIGN; DRUG MECHANISM; DRUG POTENCY; DRUG SCREENING; ENZYME ACTIVE SITE; ENZYME INHIBITION; INHIBITION KINETICS; MOLECULAR WEIGHT; REACTION OPTIMIZATION;

EID: 3142653664     PISSN: 14246376     EISSN: None     Source Type: Journal    
DOI: None     Document Type: Article

References (31)

1. Chapman, H.A.; Riese, R.J.; Shi, G.P. Annu. Rev. Physiol. 1997, 59, 63-88. Smith, W.W.; Abdel-Meguid, S.S., Exp. Opin. Ther. Patents, 1999, 9, 683-694. Henkin, J. Annu. Rep. Med. Chem. 1993, 28, 151-160. Michaud, S.; Gour, B.J., Exp. Opin. Ther. Patents, 1998, 8, 645-672. Elliott, E.; Sloane, B.F., Exp. Opin. Ther. Patents, 1996, 6, 12-32.
2. Chapman, H.A.; Riese, R.J.; Shi, G.P. Annu. Rev. Physiol. 1997, 59, 63-88. Smith, W.W.; Abdel-Meguid, S.S., Exp. Opin. Ther. Patents, 1999, 9, 683-694. Henkin, J. Annu. Rep. Med. Chem. 1993, 28, 151-160. Michaud, S.; Gour, B.J., Exp. Opin. Ther. Patents, 1998, 8, 645-672. Elliott, E.; Sloane, B.F., Exp. Opin. Ther. Patents, 1996, 6, 12-32.
3. Chapman, H.A.; Riese, R.J.; Shi, G.P. Annu. Rev. Physiol. 1997, 59, 63-88. Smith, W.W.; Abdel-Meguid, S.S., Exp. Opin. Ther. Patents, 1999, 9, 683-694. Henkin, J. Annu. Rep. Med. Chem. 1993, 28, 151-160. Michaud, S.; Gour, B.J., Exp. Opin. Ther. Patents, 1998, 8, 645-672. Elliott, E.; Sloane, B.F., Exp. Opin. Ther. Patents, 1996, 6, 12-32.
4. Chapman, H.A.; Riese, R.J.; Shi, G.P. Annu. Rev. Physiol. 1997, 59, 63-88. Smith, W.W.; Abdel-Meguid, S.S., Exp. Opin. Ther. Patents, 1999, 9, 683-694. Henkin, J. Annu. Rep. Med. Chem. 1993, 28, 151-160. Michaud, S.; Gour, B.J., Exp. Opin. Ther. Patents, 1998, 8, 645-672. Elliott, E.; Sloane, B.F., Exp. Opin. Ther. Patents, 1996, 6, 12-32.
5. Chapman, H.A.; Riese, R.J.; Shi, G.P. Annu. Rev. Physiol. 1997, 59, 63-88. Smith, W.W.; Abdel-Meguid, S.S., Exp. Opin. Ther. Patents, 1999, 9, 683-694. Henkin, J. Annu. Rep. Med. Chem. 1993, 28, 151-160. Michaud, S.; Gour, B.J., Exp. Opin. Ther. Patents, 1998, 8, 645-672. Elliott, E.; Sloane, B.F., Exp. Opin. Ther. Patents, 1996, 6, 12-32.
6. Delaisse, J.M.; Ledent, P.; Vaes, G. Biochem. J. 1991, 279, 167-174. Thomson, S.K.; Halbert, S.M.; Bossard, M.J. Proc. Natl. Acad. Sci. USA, 1997, 94, 14249-14254. Maciewicz, R.A.; Van der Stapper, J.W.J.; Paraskewa, C.; Williams, A.C.; Hague, A. Biochem. Soc. Trans. 1991, 19, 362. Esser, R.E.; Angelo, R.A.; Murphey, M.B.; Watts, L.M.; Thornburg, L.P.; Palmer, J.T.; Talhouk, J.W.; Smith, R.E., Arthritis and Rheumatism, 1994, 37, 236-247. Semenov, A.; Olson, J.E.; Rosental, P.J., Antimicrobiol agents and chemotherapy, 1998, 42, 2254-2258. Engel, C.; Doyle, P.; Hsieh, I.; McKerrow, J.H., J. Exp. Med., 1998, 188, 725-734.
7. Delaisse, J.M.; Ledent, P.; Vaes, G. Biochem. J. 1991, 279, 167-174. Thomson, S.K.; Halbert, S.M.; Bossard, M.J. Proc. Natl. Acad. Sci. USA, 1997, 94, 14249-14254. Maciewicz, R.A.; Van der Stapper, J.W.J.; Paraskewa, C.; Williams, A.C.; Hague, A. Biochem. Soc. Trans. 1991, 19, 362. Esser, R.E.; Angelo, R.A.; Murphey, M.B.; Watts, L.M.; Thornburg, L.P.; Palmer, J.T.; Talhouk, J.W.; Smith, R.E., Arthritis and Rheumatism, 1994, 37, 236-247. Semenov, A.; Olson, J.E.; Rosental, P.J., Antimicrobiol agents and chemotherapy, 1998, 42, 2254-2258. Engel, C.; Doyle, P.; Hsieh, I.; McKerrow, J.H., J. Exp. Med., 1998, 188, 725-734.
8. Delaisse, J.M.; Ledent, P.; Vaes, G. Biochem. J. 1991, 279, 167-174. Thomson, S.K.; Halbert, S.M.; Bossard, M.J. Proc. Natl. Acad. Sci. USA, 1997, 94, 14249-14254. Maciewicz, R.A.; Van der Stapper, J.W.J.; Paraskewa, C.; Williams, A.C.; Hague, A. Biochem. Soc. Trans. 1991, 19, 362. Esser, R.E.; Angelo, R.A.; Murphey, M.B.; Watts, L.M.; Thornburg, L.P.; Palmer, J.T.; Talhouk, J.W.; Smith, R.E., Arthritis and Rheumatism, 1994, 37, 236-247. Semenov, A.; Olson, J.E.; Rosental, P.J., Antimicrobiol agents and chemotherapy, 1998, 42, 2254-2258. Engel, C.; Doyle, P.; Hsieh, I.; McKerrow, J.H., J. Exp. Med., 1998, 188, 725-734.
9. Delaisse, J.M.; Ledent, P.; Vaes, G. Biochem. J. 1991, 279, 167-174. Thomson, S.K.; Halbert, S.M.; Bossard, M.J. Proc. Natl. Acad. Sci. USA, 1997, 94, 14249-14254. Maciewicz, R.A.; Van der Stapper, J.W.J.; Paraskewa, C.; Williams, A.C.; Hague, A. Biochem. Soc. Trans. 1991, 19, 362. Esser, R.E.; Angelo, R.A.; Murphey, M.B.; Watts, L.M.; Thornburg, L.P.; Palmer, J.T.; Talhouk, J.W.; Smith, R.E., Arthritis and Rheumatism, 1994, 37, 236-247. Semenov, A.; Olson, J.E.; Rosental, P.J., Antimicrobiol agents and chemotherapy, 1998, 42, 2254-2258. Engel, C.; Doyle, P.; Hsieh, I.; McKerrow, J.H., J. Exp. Med., 1998, 188, 725-734.
10. Delaisse, J.M.; Ledent, P.; Vaes, G. Biochem. J. 1991, 279, 167-174. Thomson, S.K.; Halbert, S.M.; Bossard, M.J. Proc. Natl. Acad. Sci. USA, 1997, 94, 14249-14254. Maciewicz, R.A.; Van der Stapper, J.W.J.; Paraskewa, C.; Williams, A.C.; Hague, A. Biochem. Soc. Trans. 1991, 19, 362. Esser, R.E.; Angelo, R.A.; Murphey, M.B.; Watts, L.M.; Thornburg, L.P.; Palmer, J.T.; Talhouk, J.W.; Smith, R.E., Arthritis and Rheumatism, 1994, 37, 236-247. Semenov, A.; Olson, J.E.; Rosental, P.J., Antimicrobiol agents and chemotherapy, 1998, 42, 2254-2258. Engel, C.; Doyle, P.; Hsieh, I.; McKerrow, J.H., J. Exp. Med., 1998, 188, 725-734.
11. Delaisse, J.M.; Ledent, P.; Vaes, G. Biochem. J. 1991, 279, 167-174. Thomson, S.K.; Halbert, S.M.; Bossard, M.J. Proc. Natl. Acad. Sci. USA, 1997, 94, 14249-14254. Maciewicz, R.A.; Van der Stapper, J.W.J.; Paraskewa, C.; Williams, A.C.; Hague, A. Biochem. Soc. Trans. 1991, 19, 362. Esser, R.E.; Angelo, R.A.; Murphey, M.B.; Watts, L.M.; Thornburg, L.P.; Palmer, J.T.; Talhouk, J.W.; Smith, R.E., Arthritis and Rheumatism, 1994, 37, 236-247. Semenov, A.; Olson, J.E.; Rosental, P.J., Antimicrobiol agents and chemotherapy, 1998, 42, 2254-2258. Engel, C.; Doyle, P.; Hsieh, I.; McKerrow, J.H., J. Exp. Med., 1998, 188, 725-734.
12. Reviews on cysteine proteases inhibitor: Rich, D.H. In Proteinase Inhibitors; Barrett, A.J., Salvesen, G., Eds., Elsevier: Amsterdam, 1986, p153. Demuth, H-U. J. Enzyme Inhibition, 1990, 3, 249-278. Kranz, A. Annu. Rep. Med. Chem. 1993, 28, 187-195. Otto, H.; Schirmeister, T., Chem. Rev., 1997, 97, 133-171.
13. Reviews on cysteine proteases inhibitor: Rich, D.H. In Proteinase Inhibitors; Barrett, A.J., Salvesen, G., Eds., Elsevier: Amsterdam, 1986, p153. Demuth, H-U. J. Enzyme Inhibition, 1990, 3, 249-278. Kranz, A. Annu. Rep. Med. Chem. 1993, 28, 187-195. Otto, H.; Schirmeister, T., Chem. Rev., 1997, 97, 133-171.
14. Reviews on cysteine proteases inhibitor: Rich, D.H. In Proteinase Inhibitors; Barrett, A.J., Salvesen, G., Eds., Elsevier: Amsterdam, 1986, p153. Demuth, H-U. J. Enzyme Inhibition, 1990, 3, 249-278. Kranz, A. Annu. Rep. Med. Chem. 1993, 28, 187-195. Otto, H.; Schirmeister, T., Chem. Rev., 1997, 97, 133-171.
15. Reviews on cysteine proteases inhibitor: Rich, D.H. In Proteinase Inhibitors; Barrett, A.J., Salvesen, G., Eds., Elsevier: Amsterdam, 1986, p153. Demuth, H-U. J. Enzyme Inhibition, 1990, 3, 249-278. Kranz, A. Annu. Rep. Med. Chem. 1993, 28, 187-195. Otto, H.; Schirmeister, T., Chem. Rev., 1997, 97, 133-171.
16. Hanzlik, R.P.; Jacober, S.P.; Zygmunt, J. Biochim. Biophys. Acta 1991, 1073, 33-42.
17. Hanzilk, R.P.; Zygmunt, J.; Moon, J.B. Biochim. Biophys. Acta 1990, 1035, 62-70.
18. Angelastro, M.R.; Mehdi, S.; Burkhart, J.P.; Peet, N.P.; Bey, P. J. Med. Chem. 1990, 33, 11-13. Li, Z.; Patil, G.S.; Golubski, Z.E.; Hori, H.; Tehrani, K.; Foreman, J.E.; Eveleth, D.D.; Bartus, R.T.; Powers, J.C. J. Med. Chem. 1993, 36, 3472-3480.
19. Angelastro, M.R.; Mehdi, S.; Burkhart, J.P.; Peet, N.P.; Bey, P. J. Med. Chem. 1990, 33, 11-13. Li, Z.; Patil, G.S.; Golubski, Z.E.; Hori, H.; Tehrani, K.; Foreman, J.E.; Eveleth, D.D.; Bartus, R.T.; Powers, J.C. J. Med. Chem. 1993, 36, 3472-3480.
20. Rasnick, D. Anal. Biochem. 1985, 149, 461-465.
21. Smith, R.A.; Copp, L.J.; Coles, P.J.; Pauls, H.W.; Robinson, V.J.; Spencer, R.W.; Heard, S.B.; Krantz, A. J. Am. Chem. Soc. 1988, 110, 4429-4431.
22. Gour-Salin, B.J.; Lachance, P.; Bonneau, P.R.; Storer, A.C.; Kirschke, H.; Bromme, D. Bioorg. Chem. 1994, 22, 227-241. Albeck, A.; Persky, R.; Kliper, S. Bioorg. Med. Chem. Lett. 1995, 5, 1767-1772.
23. Gour-Salin, B.J.; Lachance, P.; Bonneau, P.R.; Storer, A.C.; Kirschke, H.; Bromme, D. Bioorg. Chem. 1994, 22, 227-241. Albeck, A.; Persky, R.; Kliper, S. Bioorg. Med. Chem. Lett. 1995, 5, 1767-1772.
24. Palmer, J.T.; Rasnick, D.; Klaus, J.L.; Bromme, D. J. Med. Chem. 1995, 38, 3193-3196.
25. Tokuyama, H.; Isaka, M.; Nakamura, E.; Ando R.; Morinaka, Y. J. Am. Chem. Soc. 1993, 115, 1174-1175.
26. Conroy, J.L.; Sanders, T.C.; Seto, C.T. J. Am. Chem. Soc. 1997, 119, 4285-4291. Conroy, J.L.; Abato, P.; Ghosh, M.; Austermuhle, M.I.; Kiefer, M.R.; Seto, C.T. Tetrahedron Lett. 1998, 39, 8253-8256.
27. Conroy, J.L.; Sanders, T.C.; Seto, C.T. J. Am. Chem. Soc. 1997, 119, 4285-4291. Conroy, J.L.; Abato, P.; Ghosh, M.; Austermuhle, M.I.; Kiefer, M.R.; Seto, C.T. Tetrahedron Lett. 1998, 39, 8253-8256.
28. Zhou, N.E.; Kaleta, J.; Cameron, A.; Mecetich, R.G.; Singh, R. (Personal communication)
29. Slama, J.T.; Radziejewski, C.; Oruganti, S.; Kaiser, E.T. J. Am. Chem. Soc. 1984, 106, 6778-6785.
30. Bentley, P.H.; Hunt, E. J. Chem. Soc. Perkin Trans. I 1980, 2222-2227.
31. Barrett, A.J.; Kembhavi, A.A.; Brown, M.A.; Kirschke, H.; Knight, G.; Tamai, M.; Hanaka, K. Biochem. J. 1982, 201, 189-198.