Design, synthesis and evaluation of novel azasugar-based MMP/ADAM inhibitors

Bioorganic and Medicinal Chemistry Letters

Volumn 13, Issue 16, 2003, Pages 2741-2744

  Moriyama, Hideki ^a,b   Tsukida, Takahiro ^a,b,d   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

CARBOHYDRATE DERIVATIVE; GELATINASE B; INTERSTITIAL COLLAGENASE; MATRIX METALLOPROTEINASE INHIBITOR; METALLOPROTEINASE; PRINOMASTAT; STROMELYSIN; TUMOR NECROSIS FACTOR ALPHA CONVERTING ENZYME INHIBITOR;

ARTICLE; DRUG DESIGN; DRUG SCREENING; DRUG SYNTHESIS; ENZYME INHIBITION;

EID: 0037811296     PISSN: 0960894X     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0960-894X(03)00531-6     Document Type: Article

References (23)

1. Michaelides M.R., Curtin M.L. Curr. Pharm. Des. 5:1999;787.
2. Whittaker M., Floyd C.D., Brown P., Gearing A.J.H. Chem. Rev. 1999;2735.
3. Beckett R.P., Whittaker M. Exp. Opin. Ther. Pat. 8:1998;259.
4. Rothenberg M.L., Nelson A.R., Hande K.R. Oncologist. 3:1998;271.
5. Black R.A., White J.M. Curr. Opin. Cell. Biol. 10:1998;654.
6. Bemelmans M.H., van Tits L.J., Buurman W. Crit. Rev. Immunol. 16:1996;1.
7. 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.
8. 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. Neuroimmunol. 74:1997;85.
9. Morimoto Y., Nishikawa K., Ohashi M. Life Sci. 61:1997;795.
10. Nelson F.C., Zask A. Exp. Opin. Ther. Pat. 8:1999;383.
11. (a) Rasmunssen H.S., McCann P.P. Pharmacol. Ther. 75:1997;69.
12. (b) Beckett R.P., Davidson A.H., Drummond A.H., Huxley P., Whittaker M. Drug Disc. Today. 1:1996;16.
13. (a) Santos O., McDermott C.D., Daniels R.G., Appelt K. Clin. Exp. Metastasis. 15:1997;499.
14. (b) Zook, S. E.; Dagnino, R., Jr.; Deason, M. E.; Bender, S. L. PCT Int. Appl. WO 97/20824.
15. Hughes A.B., Rudge A.J. Nat. Prod. Rep. 11:1994;135. and ref cited therein.
16. Tamura Y., Watanabe F., Nakatani T., Yasui K., Fuji M., Komurasaki T., Tsuzuki H., Maekawa R., Yoshioka T., Kawada K., Sugita K., Ohtani M. J. Med. Chem. 41:1998;640.
17. (a) Grandel R., Kazumaier U. Tetrahedron Lett. 38:1997;8009.
18. (b) Kazumaier U., Grandel R. Synlett. 1995;945.
19. (c) Grandel R., Kazumaier U., Nuber B. Liebigs Ann. Chem. 1996;1143.
20. Mitsunobu O. Synthesis. 1981;1.
21. +).
22. (a) Recombinant human collagenase-1 (MMP-1), stromelysin-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 (b) 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.
23. (a) Recombinant human collagenase-1 (MMP-1), stromelysin-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 (b) 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.