Convenient synthesis and evaluation of enzyme inhibitory activity of several N-alkyl-, N-phenylalkyl, and cyclic isourea derivatives of 5a-Carba-α-DL-fucopyranosylamine

Bioorganic and Medicinal Chemistry Letters

Volumn 12, Issue 20, 2002, Pages 2811-2814

  Ogawa, Seiichiro ^a   Mori, Makiko ^a   Takeuchi, Goichi ^a   Doi, Fuminao ^a   Watanabe, Maiko ^a   Sakata, Yuko ^a  

^a KEIO UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

5A CARBA ALPHA DEXTRO LEVO FUCOPYRANOSYLAMINE; ALPHA LEVO FUCOSIDASE; AMINE; BETA GALACTOSIDASE; DEOXYFUCONOJIRIMYCIN; ENZYME INHIBITOR; NOJIRIMYCIN; PYRANOSIDE; UNCLASSIFIED DRUG; UREA DERIVATIVE;

ANIMAL TISSUE; ARTICLE; CHEMICAL MODIFICATION; CONTROLLED STUDY; DRUG EFFECT; DRUG POTENCY; DRUG STRUCTURE; DRUG SYNTHESIS; ENANTIOMER; ENZYME ACTIVITY; ENZYME INHIBITION; IC 50; NONHUMAN; STRUCTURE ACTIVITY RELATION;

ALPHA-L-FUCOSIDASE; ANIMALS; CATTLE; ENZYME INHIBITORS; FUCOSE; GLYCOSIDE HYDROLASES; INDICATORS AND REAGENTS; KIDNEY; MOLECULAR CONFORMATION; STRUCTURE-ACTIVITY RELATIONSHIP;

BOVINAE;

EID: 0037152486     PISSN: 0960894X     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0960-894X(02)00627-3     Document Type: Article

References (23)

1. Fan J.-Q., Ishii S., Asano N., Suzuki Y. Nat. Med. 5:1999;112.
2. Fan J.-Q., Asano N., Suzuki Y., Ishii S. Glycoconjugate J. 16:1999;S156.
3. Ogawa S., Ashiura M., Uchida C., Watanabe S. Bioorg. Med. Chem. Lett. 6:1996;929.
4. Suzuki, Y.; Nanba, E.; Ohno, K.; Matsuda, J.; Ogawa, S. Unpublished results.
5. Ogawa S., Maruyama A., Odagiri T., Yuasa H., Hashimoto H. Eur. J. Org. Chem. 2001;967, and references cited therein.
6. Ogawa S., Watanabe M., Hisamatsu S. Bioorg. Med. Chem. Lett. 2002;749.
7. Fleet G.W.J., Shaw A.N., Evans S.V., Fellows L.E. J. Chem. Soc., Chem. Commun. 1985;841.
8. Winchester B., Barker C., Baines S., Jacob G.S., Namgoong S.K., Fleet G. Biochem. J. 265:1990;277.
9. Ogawa S., Nakamoto K., Takahara M., Tannno Y., Chida N., Suami T. Bull. Chem. Soc. Jpn. 52:1979;1174.
10. Ogawa S., Oya M., Toyokuni T., Chida N., Suami T. Bull. Chem. Soc. Jpn. 56:1983;1441.
11. Ogawa S., Sekura R., Maruyama A., Yuasa H., Hashimoto H. Eur. J. Org. Chem. 2000;2089.
12. 1,5a(eq)=2.4 Hz, H-1], 0.96 (d, 3H, J 6.4 Hz, Me).
13. 2 are shown to change appreciably according to the chain-length of N-alkyl group: for example in 20a: δ 3.10, and δ 2.78 and 2.59, respectively.
14. Uchida C., Kimura H., Ogawa S. Bioorg. Med. Chem. 5:1997;921, and reference cited therein.
15. Uchida C., Yamagishi T., Ogawa S. J. Chem. Soc., Perkin Trans. 1. 1994;589.
16. 5(ax),6=5.1 Hz, H-5(ax)], 0.97 (d, 3H, J=6.6 Hz, CMe).
17. Biological assays were carried out in a standard manner by Dr. Akihiro Tomoda (Hokko Chemical Industry, Co. Ltd.), to whom our thanks are due.
18. For convenience, in this work, we used readily available racemic compounds in order to evaluate preliminary inhibitory potential.
19. Moderate inhibitory activity toward β-galactosidase seems to be exerted by the D-enantiomer, that is N-octyl-6-deoxy-5a-carba-α-D-galactopyranosylamine.
20. Fleet G.W., Karpas A., Dwek R.A., Fellows L.E., Tyms A.S., Petursson S., Namgoong S.K., Ramsden N.G., Smith P.W., Son J.C., Wilson F., Witty D.R., Jacob G., Rademacher T.W. FEBS Lett. 237:1988;128.
21. Paulsen H., Matzke M., Orthen B., Nuck R., Reutter W. Liebigs Ann. Chem. 1990;953.
22. 6 derivatives of 1 proved not to be inhibitors of α-L-fucosidase (bovine kidney): Ogawa, S.; Watanabe, M. Unpublished results.
23. Asano N., Yasuda K., Kizu H., Kato A., Fan J.-Q., Nash R.J., Fleet G.W. Eur. J. Biochem. 268:2001;35.