Novel inhibitors of procollagen C-terminal proteinase. Part 1: Diamino acid hydroxamates

Bioorganic and Medicinal Chemistry Letters

Volumn 13, Issue 13, 2003, Pages 2101-2104

  Delaet, N G J ^a,c   Robinson, L A ^a   Wilson, D M ^a,d   Sullivan, R W ^a,c   Bradley, E K ^a,e   Dankwardt, S M ^b   Martin, R L ^b   Van Wart, H E ^b,f   Walker, K A M ^b  

^a Formerly CombiChem Inc   (United States)

^b ROCHE BIOSCIENCE   (United States)

^c Kemia Inc   (United States)

^d VERTEX PHARMACEUTICALS   (United States)

^e Sunesis Pharmaceuticals Inc   (United States)

^f Metabolix Inc   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

DIAMINO ACID; HYDROXAMIC ACID DERIVATIVE; HYDROXYL GROUP; METALLOPROTEINASE INHIBITOR; PROCOLLAGEN C PROTEINASE; PROPIONIC ACID; REAGENT; RESIN; SOLVENT;

ALKYLATION; AMINO TERMINAL SEQUENCE; ARTICLE; BINDING KINETICS; CARBOXY TERMINAL SEQUENCE; DEPROTECTION REACTION; DERIVATIZATION; DRUG CONFORMATION; DRUG EFFECT; DRUG MECHANISM; DRUG POTENCY; DRUG SYNTHESIS; MITSUNOBU REACTION; REACTION ANALYSIS; SUBSTITUTION REACTION;

EID: 0038240690     PISSN: 0960894X     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0960-894X(03)00404-9     Document Type: Article

References (16)

1. Kessler E. Proc. Indian Acad. Sci. (Chem. Sci.). 111:1999;197. and references therein.
2. Bode W., Gomis-Ruth F.X., Stöcker W. FEBS Lett. 331:1993;134.
3. Rasmussen H.S., McCann P.P. Pharmacol. Ther. 75:1997;69.
4. Since this work, other researchers have identified hydroxamates as inhibitors of PCP. See for example: Brenner, M., Ho, W.-B. WO patent 97/05865. Ovens, A.; Joule, J. A.; Kadler, K. E. J. Pept. Sci. 2000, 6, 489. Bailey S.; Billotte, S.; Derrick, A. M.; Fish, P. V.; James, K.; Thomson, N. M. WO patent 01/47901. Ho, W.-B.; Bauer, U. WO patent 01/56996.
5. Since this work, other researchers have identified hydroxamates as inhibitors of PCP. See for example: Brenner, M., Ho, W.-B. WO patent 97/05865. Ovens, A.; Joule, J. A.; Kadler, K. E. J. Pept. Sci. 2000, 6, 489. Bailey S.; Billotte, S.; Derrick, A. M.; Fish, P. V.; James, K.; Thomson, N. M. WO patent 01/47901. Ho, W.-B.; Bauer, U. WO patent 01/56996.
6. For approaches in solution see for example: Barlaam B., Hamon A., Maudet M. Tetrahedron Lett. 39:1998;7865 MacPherson L.J., Bayburt E.K., Capparelli M.P., Carroll B.J., Goldstein R., Justice M.R., Zhu L., Hu S., Melton R.A., Fryer L., Goldberg R.L., Doughty J.R., Spiroti S., Blancuzzi V., Wilson D., O'Byrne E.M., Ganu V., Parker D.T. J. Med. Chem. 40:1997;2525 Caldarelli M., Habermann J., Ley S.V. Bioorg. Med. Chem. Lett. 9:1999;2049. For examples of solid supported approaches, see: Ngu K., Patel D.V. J. Org. Chem. 62:1997;7088 Floyd C.D., Lewis C.N., Patel S.R., Whittaker M. Tetrahedron Lett. 37:1996;2625 Mellor S.L., McGuire C., Chan W.C. Tetrahedron Lett. 38:1997;3311 Golebioski A., Klopfenstein S. Tetrahedron Lett. 39:1998;3397.
7. For approaches in solution see for example: Barlaam B., Hamon A., Maudet M. Tetrahedron Lett. 39:1998;7865 MacPherson L.J., Bayburt E.K., Capparelli M.P., Carroll B.J., Goldstein R., Justice M.R., Zhu L., Hu S., Melton R.A., Fryer L., Goldberg R.L., Doughty J.R., Spiroti S., Blancuzzi V., Wilson D., O'Byrne E.M., Ganu V., Parker D.T. J. Med. Chem. 40:1997;2525 Caldarelli M., Habermann J., Ley S.V. Bioorg. Med. Chem. Lett. 9:1999;2049. For examples of solid supported approaches, see: Ngu K., Patel D.V. J. Org. Chem. 62:1997;7088 Floyd C.D., Lewis C.N., Patel S.R., Whittaker M. Tetrahedron Lett. 37:1996;2625 Mellor S.L., McGuire C., Chan W.C. Tetrahedron Lett. 38:1997;3311 Golebioski A., Klopfenstein S. Tetrahedron Lett. 39:1998;3397.
8. For approaches in solution see for example: Barlaam B., Hamon A., Maudet M. Tetrahedron Lett. 39:1998;7865 MacPherson L.J., Bayburt E.K., Capparelli M.P., Carroll B.J., Goldstein R., Justice M.R., Zhu L., Hu S., Melton R.A., Fryer L., Goldberg R.L., Doughty J.R., Spiroti S., Blancuzzi V., Wilson D., O'Byrne E.M., Ganu V., Parker D.T. J. Med. Chem. 40:1997;2525 Caldarelli M., Habermann J., Ley S.V. Bioorg. Med. Chem. Lett. 9:1999;2049. For examples of solid supported approaches, see: Ngu K., Patel D.V. J. Org. Chem. 62:1997;7088 Floyd C.D., Lewis C.N., Patel S.R., Whittaker M. Tetrahedron Lett. 37:1996;2625 Mellor S.L., McGuire C., Chan W.C. Tetrahedron Lett. 38:1997;3311 Golebioski A., Klopfenstein S. Tetrahedron Lett. 39:1998;3397.
9. For approaches in solution see for example: Barlaam B., Hamon A., Maudet M. Tetrahedron Lett. 39:1998;7865 MacPherson L.J., Bayburt E.K., Capparelli M.P., Carroll B.J., Goldstein R., Justice M.R., Zhu L., Hu S., Melton R.A., Fryer L., Goldberg R.L., Doughty J.R., Spiroti S., Blancuzzi V., Wilson D., O'Byrne E.M., Ganu V., Parker D.T. J. Med. Chem. 40:1997;2525 Caldarelli M., Habermann J., Ley S.V. Bioorg. Med. Chem. Lett. 9:1999;2049. For examples of solid supported approaches, see: Ngu K., Patel D.V. J. Org. Chem. 62:1997;7088 Floyd C.D., Lewis C.N., Patel S.R., Whittaker M. Tetrahedron Lett. 37:1996;2625 Mellor S.L., McGuire C., Chan W.C. Tetrahedron Lett. 38:1997;3311 Golebioski A., Klopfenstein S. Tetrahedron Lett. 39:1998;3397.
10. For approaches in solution see for example: Barlaam B., Hamon A., Maudet M. Tetrahedron Lett. 39:1998;7865 MacPherson L.J., Bayburt E.K., Capparelli M.P., Carroll B.J., Goldstein R., Justice M.R., Zhu L., Hu S., Melton R.A., Fryer L., Goldberg R.L., Doughty J.R., Spiroti S., Blancuzzi V., Wilson D., O'Byrne E.M., Ganu V., Parker D.T. J. Med. Chem. 40:1997;2525 Caldarelli M., Habermann J., Ley S.V. Bioorg. Med. Chem. Lett. 9:1999;2049. For examples of solid supported approaches, see: Ngu K., Patel D.V. J. Org. Chem. 62:1997;7088 Floyd C.D., Lewis C.N., Patel S.R., Whittaker M. Tetrahedron Lett. 37:1996;2625 Mellor S.L., McGuire C., Chan W.C. Tetrahedron Lett. 38:1997;3311 Golebioski A., Klopfenstein S. Tetrahedron Lett. 39:1998;3397.
11. For approaches in solution see for example: Barlaam B., Hamon A., Maudet M. Tetrahedron Lett. 39:1998;7865 MacPherson L.J., Bayburt E.K., Capparelli M.P., Carroll B.J., Goldstein R., Justice M.R., Zhu L., Hu S., Melton R.A., Fryer L., Goldberg R.L., Doughty J.R., Spiroti S., Blancuzzi V., Wilson D., O'Byrne E.M., Ganu V., Parker D.T. J. Med. Chem. 40:1997;2525 Caldarelli M., Habermann J., Ley S.V. Bioorg. Med. Chem. Lett. 9:1999;2049. For examples of solid supported approaches, see: Ngu K., Patel D.V. J. Org. Chem. 62:1997;7088 Floyd C.D., Lewis C.N., Patel S.R., Whittaker M. Tetrahedron Lett. 37:1996;2625 Mellor S.L., McGuire C., Chan W.C. Tetrahedron Lett. 38:1997;3311 Golebioski A., Klopfenstein S. Tetrahedron Lett. 39:1998;3397.
12. For approaches in solution see for example: Barlaam B., Hamon A., Maudet M. Tetrahedron Lett. 39:1998;7865 MacPherson L.J., Bayburt E.K., Capparelli M.P., Carroll B.J., Goldstein R., Justice M.R., Zhu L., Hu S., Melton R.A., Fryer L., Goldberg R.L., Doughty J.R., Spiroti S., Blancuzzi V., Wilson D., O'Byrne E.M., Ganu V., Parker D.T. J. Med. Chem. 40:1997;2525 Caldarelli M., Habermann J., Ley S.V. Bioorg. Med. Chem. Lett. 9:1999;2049. For examples of solid supported approaches, see: Ngu K., Patel D.V. J. Org. Chem. 62:1997;7088 Floyd C.D., Lewis C.N., Patel S.R., Whittaker M. Tetrahedron Lett. 37:1996;2625 Mellor S.L., McGuire C., Chan W.C. Tetrahedron Lett. 38:1997;3311 Golebioski A., Klopfenstein S. Tetrahedron Lett. 39:1998;3397.
13. A variation of this synthetic route was published by us previously, as it applied to the synthesis of related compounds based on ornithine. See: Dankwardt S.M., Martin R.L., Chan C.S., Van Wart H.E., Walkder K.A.M., Delaet N., Robinson L.A. Bioorg. Med. Chem. Lett. 10:2000;2513.
14. Nash I.A., Bycroft B.W., Chan W.C. Tetrahedron Lett. 37:1996;2625.
15. Details of the PCP assay can be found in Billedeau, R. J.; Broka, C. A.; Campbell, J. A.; Chen, J. J.; Dankwardt, S. M.; Delaet, N.; Robinson, L. A.; Walker, K. A. M. WO patent 00/37436, 2000, p.108.
16. Our optimization of the Orn derivatives was published previously, see ref 6.