Synthesis and biological activity of selective azasugar-based TACE inhibitors

Bioorganic and Medicinal Chemistry Letters

Volumn 14, Issue 6, 2004, Pages 1569-1572

  Tsukida, Takahiro ^a,b,d   Moriyama, Hideki ^a,b   Inoue, Yoshimasa ^b   Kondo, Hirosato ^b,d   Yoshino, Kohichiro ^b   Nishimura, Shin Ichiro ^c  

^a Japan Bioindustry Association   (Japan)

^b Nippon Organon KK   (Japan)

^c HOKKAIDO UNIVERSITY   (Japan)

^d SHIONOGI AND CO LTD   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

ACETIC ACID DERIVATIVE; AZASUGAR; GELATINASE B; HYDROXAMIC ACID DERIVATIVE; STROMELYSIN; SUGAR; TUMOR NECROSIS FACTOR ALPHA CONVERTING ENZYME INHIBITOR; UNCLASSIFIED DRUG;

ARTICLE; DRUG ACTIVITY; DRUG DESIGN; DRUG FORMULATION; DRUG POTENCY; DRUG SELECTIVITY; DRUG SYNTHESIS;

ADAM PROTEINS; AZA COMPOUNDS; HUMANS; METALLOENDOPEPTIDASES; PROTEASE INHIBITORS; SUGAR ACIDS;

EID: 1542314917     PISSN: 0960894X     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.bmcl.2003.12.091     Document Type: Article

References (24)

1. Moreland L.W., Baumgartner S.W., Schiff M.H., Tindall E.A., Fleischmann R.M., Weaver A.L., Ettlinger R.E., Cohen S., Koopman W.J., Mohler K. N. Engl. J. Med. 337:1997;141.
2. Clements J.M., Cossins J.A., Wells G.M., Corkill D.J., Helfrich K., Wood L.M., Pigott R., Stabler G., Ward G.A., Gearing A.J., Miller K.M. J. NeTACE activity uroimmunol. 74:1997;85.
3. Morimoto Y., Nishikawa K., Ohashi M. Life Sci. 61:1997;795.
4. Aggarwal B.B., Kohr W.J., Hass P.E., Moffat B., Spencer S.A., Henzel W.J., Bringman T.S., Nedwin G.E., Goeddel D.V., Harkins R.N. J. Biol. Chem. 260:1985;2345.
5. Tracy K.J., Cerami A. Annu. Rev. Med. 45:1994;491.
6. Aggarwal B.B., Natarajan K. Euro. Cytokine. Net. 7:1996;93.
7. Bemelmans M.H.A., van Tits L.J.H., Buurman W.A. Crit. Rev. Immunol. 16:1996;1.
8. Moss, M.; Becherer, J. D.; Milla, M.; Pahel, G.; Lambert, M.; Andrews, R.; Frye, S.; Haffner, C.; Cowan, D.; Maloney, P.; Dixon, E. P.; Jansen, M.; Vitek, M. P.; Mitchell, J.; Leesnitzer, T.; Warner, J.; Conway, J.; Bickett, D. M.; Bird, M.; Priest, R.; Reinhard, J.; Lin, P. In Metalloproteinases as Targets for Anti-inflammatory Drugs; Bottomley, K. M. K., Bradshaw, D., Nixon, J. S., Eds.; Birkhauser: Basel, 1999; p187.
9. Killar L., White J., Black R., Peschon J. Ann. N. Y. Acad. Sci. 878:1999;442.
10. Nelson F.C., Zask A. Exp. Opin. Ther. Patents. 8:1999;383.
11. Lorenz H.M. Curr. Opin. Invest. Drugs. 1:2000;188.
12. McGeehan G., Becherer J., Bast R., Boyer C., Champion B., Connolly K., Conway J., Furdon P., Karp S., Kidao S., McElroy A., Nichols J., Pryzwansky K., Schoenen F., Sekut L., Truesdale A., Verghese M., Warner J., Ways J. Nature. 370:1994;558.
13. Gearing A., Beckett M., Christodoulou M., Churchill M., Clements J., Davidson A., Drummond A., Galloway W., Gilbert R., Gordon J., Leber T., Mangan M., Miller K., Nayee P., Owens K., Patel S., Thomas W., Wells G., Wood L., Wooly K. Nature. 370:1994;555.
14. Rasmunssen H.S., McCann P.P. Pharmacol. Ther. 75:1997;69.
15. Beckett R.P., Davidson A.H., Drummond A.H., Huxley P., Whittaker M. Drug Disc. Today. 1:1996;16.
16. Santos O., McDermott C.D., Daniels R.G., Appelt K. Clin. Exp. Metastasis. 15:1997;499.
17. Zook, S. E.; Dagnino, R., Jr.; Deason, M. E.; Bender, S. L.; Melnick, M. J. PCT Int. Appl. WO 97/20824.
18. James M.C., Guixian J., Amy S., Jeremy I.L. Bioorg. Med. Chem. Lett. 12:2002;1195.
19. Moriyama H., Tsukida T., Inoue Y., Kondo H., Yoshino K., Nishimura S.-I. Bioorg. Med. Chem. Lett. 13:2003;2737.
20. Moriyama H., Tsukida T., Inoue Y., Kondo H., Yoshino K., Nishimura S.-I. Bioorg. Med. Chem. Lett. 13:2003;2741.
21. Moriyama, H.; Tsukida, T.; Inoue, Y.; Yokota, K.; Yoshino, K.; Kondo, H. ; Miura, N.; Nishimura, S.-I. J. Med. Chem., in press.
22. +).
23. Recombinant human collagenase-1 (MMP-1), strome- lysin-1 (MMP-3), gelatinase B (MMP-9) and TNF-α converting enzyme (TACE) were used in our studies. Assay conditions were referred as below: Sawa M., Kiyoi T., Kurokawa K., Kumihara H., Yamamoto M., Miyasaka T., Ito Y., Hirayama R., Inoue T., Kirii Y., Nishiwaki E., Ohmoto H., Maeda Y., Ishibushi E., Inoue Y., Yoshino K., Kondo H. J. Med. Chem. 45:2002;919.
24. Yoshiizumi K., Yamamoto M., Miyasaka T., Ito Y., Kumihara H., Sawa M., Kiyoi T., Yamamoto T., Nakajima F., Hirayama R., Kondo H., Ishibushi E., Ohmoto H., Inoue Y., Yoshino K. Bioorg. Med. Chem. 11:2003;433.