Synthesis and evaluation of glucocerebrosidase inhibitory activity of anhydro deoxyinositols from (+)-epi- and (-)-vibo-quercitols

Bioorganic and Medicinal Chemistry Letters

Volumn 9, Issue 11, 1999, Pages 1493-1498

  Ogawa, Seiichiro ^a   Uetsuki, Satoko ^a   Tezuka, Yoji ^a   Morikawa, Takayuki ^a   Takahashi, Atsushi ^b   Sato, Kiyoshi ^b  

^a KEIO UNIVERSITY   (Japan)

^b Hokko Chemical Industry Co Ltd ^*  (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

CONDURITOL B EPOXIDE; EPIQUERCITOL; GLUCOSYLCERAMIDASE; INOSITOL DERIVATIVE; QUERCITOL DERIVATIVE; UNCLASSIFIED DRUG; VIBOQUERCITOL;

ARTICLE; CHEMICAL MODIFICATION; CHEMICAL STRUCTURE; ENZYME ACTIVITY; EPOXIDATION; MOUSE; NONHUMAN; SYNTHESIS;

ANIMALS; GLUCOSYLCERAMIDASE; INOSITOL; LIVER; MAGNETIC RESONANCE SPECTROSCOPY; MICE; MODELS, CHEMICAL;

EID: 0033532709     PISSN: 0960894X     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0960-894X(99)00223-1     Document Type: Article

References (19)

1. 6 and Other Rice Components, Kyoto, 1998, June 8-9, Abstract PS-64.
2. Presented part at the 74th Annual Meeting of Japan Chemical Society, Tanabe, Kyoto, 1998, March 27-30, 3 E6 05, Abstract II, p 1103..
3. Atsumi, S.; Umezawa, K.; Iinuma, H.; Nakamura, H.; Iitaka, Y.; Takeuchi, T. J. Antibiot., 1990, 43, 49.
4. Lee, K. J.; Boyd, S. A.; Radin N. S. Carbohydr. Res. 1985, 144, 148, references cited therein.
5. Legler, G.; Bieberich, E.; Arch. Biochem. Biophys. 1988, 260, 437. For biochemical application, see van Weekly, S.; van den Berg, M.; Barranger, J. A.; Sa Miranda, M. C; Tager, J. M.; Aerts, J. M. F. G. J. Clin. Invest. 1993, 91, 1167, references cited therein.
6. Legler, G.; Bieberich, E.; Arch. Biochem. Biophys. 1988, 260, 437. For biochemical application, see van Weekly, S.; van den Berg, M.; Barranger, J. A.; Sa Miranda, M. C; Tager, J. M.; Aerts, J. M. F. G. J. Clin. Invest. 1993, 91, 1167, references cited therein.
7. (a) Legler, G. Advan. Carbohydr. Chem. Biochem., 1990, 48, 319. (b) Look, G.; Fotsch, C. H.; Wong, C-H. Acc. Chem. Res. 1993, 26, 182. (c) Legler, G. Carbohydrate Mimics; Chapleur, Y. Ed.; Wiley-VCH: Weinheim, 1998; pp. 463-490.
8. (a) Legler, G. Advan. Carbohydr. Chem. Biochem., 1990, 48, 319. (b) Look, G.; Fotsch, C. H.; Wong, C-H. Acc. Chem. Res. 1993, 26, 182. (c) Legler, G. Carbohydrate Mimics; Chapleur, Y. Ed.; Wiley-VCH: Weinheim, 1998; pp. 463-490.
9. (a) Legler, G. Advan. Carbohydr. Chem. Biochem., 1990, 48, 319. (b) Look, G.; Fotsch, C. H.; Wong, C-H. Acc. Chem. Res. 1993, 26, 182. (c) Legler, G. Carbohydrate Mimics; Chapleur, Y. Ed.; Wiley-VCH: Weinheim, 1998; pp. 463-490.
10. (a) McCasland, G. E. Advan. Carbohydr. Chem. 1965, 20, 12. (b) Anderson, L. The Carbohydrates IA, Pigman, W.; Horton, D. Ed.; Academic Press, New York and London, 1972, pp 519-579.
11. (a) McCasland, G. E. Advan. Carbohydr. Chem. 1965, 20, 12. (b) Anderson, L. The Carbohydrates IA, Pigman, W.; Horton, D. Ed.; Academic Press, New York and London, 1972, pp 519-579.
12. In this paper, Nomenclature of cyclitols follows IUPAC-IUB 1973 recommendations for cyclitol (Pure Appl. Chem., 1974, 37, 285).
13. Recently, (+)-epi-quercitol has been synthesized from d-galactose: Dubreuil, D.; Cleophax, J.; de Almeida, M. V.; Verre-Sebrié, C.; Liaigre, J.; Vass, G.; Gero, S. D. Tetrahedron, 1997, 53, 16747.
14. 1H NMR spectra and elementary analyses.
15. The pentols 1 and 3 were treated with 7 molar equiv of benzoyl chloride in pyridine at room temperature for 2-3 days, giving the tetrabenzoates (∼60% isolated yield), together with the pentabenzoates (∼10%).
16. (a) Inokuchi, J.-i.; Jimbo, M.; Momosaki, K.; Shimeno, H.; Nagamatsu, A.; Radin, N. S. Cancer Res. 1990, 50, 6731. (b) Radin, N. S.; Shayman, J. A.; Inokuchi, J.-i. Advan. Lipid Res. 1993, 183.
17. (a) Inokuchi, J.-i.; Jimbo, M.; Momosaki, K.; Shimeno, H.; Nagamatsu, A.; Radin, N. S. Cancer Res. 1990, 50, 6731. (b) Radin, N. S.; Shayman, J. A.; Inokuchi, J.-i. Advan. Lipid Res. 1993, 183.
18. Raghavan, S.; Krusell, A. Biochim. Biophys. Acta. 1986, 877, 1.
19. -6 M) against glucocerebrosidase (mouse liver): Ogawa, S.; Ashiura, M.; Uchida, C.; Watanabe, S.; Yamazaki, C.; Yamagishi, K.; Inokuchi, J.-i. Bioorg. Med. Chem. Lett., 1996, 6, 929.