Thio-sugars IV: Design and synthesis of S-linked fucoside analogs as a new class of α-L-fucosidase inhibitors

Bioorganic and Medicinal Chemistry Letters

Volumn 8, Issue 22, 1998, Pages 3265-3268

  Witczak, Zbigniew J ^a   Boryczewski, Dina ^a  

^a UNIVERSITY OF CONNECTICUT   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ALPHA LEVO FUCOSIDASE; ALPHA LEVO FUCOSIDASE INHIBITOR; ALPHA1 THIO LEVO FRUCOSE DERIVATIVE; ENZYME INHIBITOR; THIOL DERIVATIVE; UNCLASSIFIED DRUG;

ACETYLATION; ARTICLE; CATALYSIS; DRUG STRUCTURE; DRUG SYNTHESIS; PURIFICATION; REACTION ANALYSIS; REDUCTION; STRUCTURE ANALYSIS;

EID: 0032542079     PISSN: 0960894X     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0960-894X(98)00596-4     Document Type: Article

References (32)

1. th American Chemical Society Meeting during Fucosidase and Glucosidase Inhibitors Symposium, Dallas, TX, March 29-April 1, 1998. Abstract CARB. 061.
2. 2. For review see: Defaye, J.; Gelas, J. In Studies in Natural Products Chemistry; Atta-ur-Rahman, Ed.; Elsevier, Amsterdam, 1991; Vol. 8E, pp 315-357; For various approaches to S-thiodisaccharides see: Blanc-Muesser, M.; Defaye, J.; Driguez, H. J. Chem. Soc. Perkin Trans. 1, 1982, 15; Hashimoto, H. Shimada, K.; Horito, S. Tetrahedron Lett. 1993, 34, 4953; Hashimoto, H. Shimada, K.; Horito, S., Tetrahedron: Asymmetry 1994, 12, 2351; Comber, R. N.; Friedrich J. D.; Dunshee, D. A.; Petty, S. L.; Secrist, III, J. A. Carbohydr. Res. 1994, 262, 245; Calvo-Asin, J. A.; Calvo-Flores, F. G.; Exposito-Lopez, J. M.; Hernandez-Mateo F.; Garcia-Lopez, J. J.; Isac-Garcia, J.; Santoyo-Gonzalez, F.; Vargas-Berenguel A. J. Chem. Soc. Perkin Trans. 1, 1997, 1079; Petrusova, M.; Lattova, E.; Petrus, L.; BeMiller, J. N. Carbohydr. Res. 1996, 283, 73; Michael, K.; Kessler, H. Tetrahedron Lett. 1996, 37, 3453; Becker, B.; Thimm, J.; Thiem, J., J. Carbohydr.Chem. 1996, 15, 1179.
3. 2. For review see: Defaye, J.; Gelas, J. In Studies in Natural Products Chemistry; Atta-ur-Rahman, Ed.; Elsevier, Amsterdam, 1991; Vol. 8E, pp 315-357; For various approaches to S-thiodisaccharides see: Blanc-Muesser, M.; Defaye, J.; Driguez, H. J. Chem. Soc. Perkin Trans. 1, 1982, 15; Hashimoto, H. Shimada, K.; Horito, S. Tetrahedron Lett. 1993, 34, 4953; Hashimoto, H. Shimada, K.; Horito, S., Tetrahedron: Asymmetry 1994, 12, 2351; Comber, R. N.; Friedrich J. D.; Dunshee, D. A.; Petty, S. L.; Secrist, III, J. A. Carbohydr. Res. 1994, 262, 245; Calvo-Asin, J. A.; Calvo-Flores, F. G.; Exposito-Lopez, J. M.; Hernandez-Mateo F.; Garcia-Lopez, J. J.; Isac-Garcia, J.; Santoyo-Gonzalez, F.; Vargas-Berenguel A. J. Chem. Soc. Perkin Trans. 1, 1997, 1079; Petrusova, M.; Lattova, E.; Petrus, L.; BeMiller, J. N. Carbohydr. Res. 1996, 283, 73; Michael, K.; Kessler, H. Tetrahedron Lett. 1996, 37, 3453; Becker, B.; Thimm, J.; Thiem, J., J. Carbohydr.Chem. 1996, 15, 1179.
4. 2. For review see: Defaye, J.; Gelas, J. In Studies in Natural Products Chemistry; Atta-ur-Rahman, Ed.; Elsevier, Amsterdam, 1991; Vol. 8E, pp 315-357; For various approaches to S-thiodisaccharides see: Blanc-Muesser, M.; Defaye, J.; Driguez, H. J. Chem. Soc. Perkin Trans. 1, 1982, 15; Hashimoto, H. Shimada, K.; Horito, S. Tetrahedron Lett. 1993, 34, 4953; Hashimoto, H. Shimada, K.; Horito, S., Tetrahedron: Asymmetry 1994, 12, 2351; Comber, R. N.; Friedrich J. D.; Dunshee, D. A.; Petty, S. L.; Secrist, III, J. A. Carbohydr. Res. 1994, 262, 245; Calvo-Asin, J. A.; Calvo-Flores, F. G.; Exposito-Lopez, J. M.; Hernandez-Mateo F.; Garcia-Lopez, J. J.; Isac-Garcia, J.; Santoyo-Gonzalez, F.; Vargas-Berenguel A. J. Chem. Soc. Perkin Trans. 1, 1997, 1079; Petrusova, M.; Lattova, E.; Petrus, L.; BeMiller, J. N. Carbohydr. Res. 1996, 283, 73; Michael, K.; Kessler, H. Tetrahedron Lett. 1996, 37, 3453; Becker, B.; Thimm, J.; Thiem, J., J. Carbohydr.Chem. 1996, 15, 1179.
5. 2. For review see: Defaye, J.; Gelas, J. In Studies in Natural Products Chemistry; Atta-ur-Rahman, Ed.; Elsevier, Amsterdam, 1991; Vol. 8E, pp 315-357; For various approaches to S-thiodisaccharides see: Blanc-Muesser, M.; Defaye, J.; Driguez, H. J. Chem. Soc. Perkin Trans. 1, 1982, 15; Hashimoto, H. Shimada, K.; Horito, S. Tetrahedron Lett. 1993, 34, 4953; Hashimoto, H. Shimada, K.; Horito, S., Tetrahedron: Asymmetry 1994, 12, 2351; Comber, R. N.; Friedrich J. D.; Dunshee, D. A.; Petty, S. L.; Secrist, III, J. A. Carbohydr. Res. 1994, 262, 245; Calvo-Asin, J. A.; Calvo-Flores, F. G.; Exposito-Lopez, J. M.; Hernandez-Mateo F.; Garcia-Lopez, J. J.; Isac-Garcia, J.; Santoyo-Gonzalez, F.; Vargas-Berenguel A. J. Chem. Soc. Perkin Trans. 1, 1997, 1079; Petrusova, M.; Lattova, E.; Petrus, L.; BeMiller, J. N. Carbohydr. Res. 1996, 283, 73; Michael, K.; Kessler, H. Tetrahedron Lett. 1996, 37, 3453; Becker, B.; Thimm, J.; Thiem, J., J. Carbohydr.Chem. 1996, 15, 1179.
6. 2. For review see: Defaye, J.; Gelas, J. In Studies in Natural Products Chemistry; Atta-ur-Rahman, Ed.; Elsevier, Amsterdam, 1991; Vol. 8E, pp 315-357; For various approaches to S-thiodisaccharides see: Blanc-Muesser, M.; Defaye, J.; Driguez, H. J. Chem. Soc. Perkin Trans. 1, 1982, 15; Hashimoto, H. Shimada, K.; Horito, S. Tetrahedron Lett. 1993, 34, 4953; Hashimoto, H. Shimada, K.; Horito, S., Tetrahedron: Asymmetry 1994, 12, 2351; Comber, R. N.; Friedrich J. D.; Dunshee, D. A.; Petty, S. L.; Secrist, III, J. A. Carbohydr. Res. 1994, 262, 245; Calvo-Asin, J. A.; Calvo-Flores, F. G.; Exposito-Lopez, J. M.; Hernandez-Mateo F.; Garcia-Lopez, J. J.; Isac-Garcia, J.; Santoyo-Gonzalez, F.; Vargas-Berenguel A. J. Chem. Soc. Perkin Trans. 1, 1997, 1079; Petrusova, M.; Lattova, E.; Petrus, L.; BeMiller, J. N. Carbohydr. Res. 1996, 283, 73; Michael, K.; Kessler, H. Tetrahedron Lett. 1996, 37, 3453; Becker, B.; Thimm, J.; Thiem, J., J. Carbohydr.Chem. 1996, 15, 1179.
7. 2. For review see: Defaye, J.; Gelas, J. In Studies in Natural Products Chemistry; Atta-ur-Rahman, Ed.; Elsevier, Amsterdam, 1991; Vol. 8E, pp 315-357; For various approaches to S-thiodisaccharides see: Blanc-Muesser, M.; Defaye, J.; Driguez, H. J. Chem. Soc. Perkin Trans. 1, 1982, 15; Hashimoto, H. Shimada, K.; Horito, S. Tetrahedron Lett. 1993, 34, 4953; Hashimoto, H. Shimada, K.; Horito, S., Tetrahedron: Asymmetry 1994, 12, 2351; Comber, R. N.; Friedrich J. D.; Dunshee, D. A.; Petty, S. L.; Secrist, III, J. A. Carbohydr. Res. 1994, 262, 245; Calvo-Asin, J. A.; Calvo-Flores, F. G.; Exposito-Lopez, J. M.; Hernandez-Mateo F.; Garcia-Lopez, J. J.; Isac-Garcia, J.; Santoyo-Gonzalez, F.; Vargas-Berenguel A. J. Chem. Soc. Perkin Trans. 1, 1997, 1079; Petrusova, M.; Lattova, E.; Petrus, L.; BeMiller, J. N. Carbohydr. Res. 1996, 283, 73; Michael, K.; Kessler, H. Tetrahedron Lett. 1996, 37, 3453; Becker, B.; Thimm, J.; Thiem, J., J. Carbohydr.Chem. 1996, 15, 1179.
8. 2. For review see: Defaye, J.; Gelas, J. In Studies in Natural Products Chemistry; Atta-ur-Rahman, Ed.; Elsevier, Amsterdam, 1991; Vol. 8E, pp 315-357; For various approaches to S-thiodisaccharides see: Blanc-Muesser, M.; Defaye, J.; Driguez, H. J. Chem. Soc. Perkin Trans. 1, 1982, 15; Hashimoto, H. Shimada, K.; Horito, S. Tetrahedron Lett. 1993, 34, 4953; Hashimoto, H. Shimada, K.; Horito, S., Tetrahedron: Asymmetry 1994, 12, 2351; Comber, R. N.; Friedrich J. D.; Dunshee, D. A.; Petty, S. L.; Secrist, III, J. A. Carbohydr. Res. 1994, 262, 245; Calvo-Asin, J. A.; Calvo-Flores, F. G.; Exposito-Lopez, J. M.; Hernandez-Mateo F.; Garcia-Lopez, J. J.; Isac-Garcia, J.; Santoyo-Gonzalez, F.; Vargas-Berenguel A. J. Chem. Soc. Perkin Trans. 1, 1997, 1079; Petrusova, M.; Lattova, E.; Petrus, L.; BeMiller, J. N. Carbohydr. Res. 1996, 283, 73; Michael, K.; Kessler, H. Tetrahedron Lett. 1996, 37, 3453; Becker, B.; Thimm, J.; Thiem, J., J. Carbohydr.Chem. 1996, 15, 1179.
9. 2. For review see: Defaye, J.; Gelas, J. In Studies in Natural Products Chemistry; Atta-ur-Rahman, Ed.; Elsevier, Amsterdam, 1991; Vol. 8E, pp 315-357; For various approaches to S-thiodisaccharides see: Blanc-Muesser, M.; Defaye, J.; Driguez, H. J. Chem. Soc. Perkin Trans. 1, 1982, 15; Hashimoto, H. Shimada, K.; Horito, S. Tetrahedron Lett. 1993, 34, 4953; Hashimoto, H. Shimada, K.; Horito, S., Tetrahedron: Asymmetry 1994, 12, 2351; Comber, R. N.; Friedrich J. D.; Dunshee, D. A.; Petty, S. L.; Secrist, III, J. A. Carbohydr. Res. 1994, 262, 245; Calvo-Asin, J. A.; Calvo-Flores, F. G.; Exposito-Lopez, J. M.; Hernandez-Mateo F.; Garcia-Lopez, J. J.; Isac-Garcia, J.; Santoyo-Gonzalez, F.; Vargas-Berenguel A. J. Chem. Soc. Perkin Trans. 1, 1997, 1079; Petrusova, M.; Lattova, E.; Petrus, L.; BeMiller, J. N. Carbohydr. Res. 1996, 283, 73; Michael, K.; Kessler, H. Tetrahedron Lett. 1996, 37, 3453; Becker, B.; Thimm, J.; Thiem, J., J. Carbohydr.Chem. 1996, 15, 1179.
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24. 3).
25. 3).
26. 9S: 365.35. Found: 365.07.
27. 8S: 377.40. Found: 377.07.
28. 5S: 251.29. Found: 251.08.
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30. 3-C-6), 42.9 (C-2′), 69.2 (C-5), 70.8 (C-2), 72.0 (C-3), 73.9 (C-4), 99.0 (C1).
31. 15. The typical enzyme assays were performed at 25 °C and 37 °C for 45 min in 20 mM citrate buffer (pH 5.5 for bovine kidney, 300 mL) which contained the following assay components: p-nitrophenyl fucoside (0.07-033 mM), compound 4 or 5 (each 0-6.7 mM) α-L-fucosidase (0.8-1.1 units/mL). Initial velocities (less than 10% substrate consumed) were measured by quenching the reaction after 45 min by the addition of 50 mL of glycine buffer (pH 10.00, 500 μL and determining the released p-nitrophenolate ion concentration by visible absorption spectroscopy at 400 nm. (reference, same solution without enzyme).
32. 16. Evans, S.V.; Fellows, L. E.; Shing, T. K. M.; Fleet, G. W. J. Phytochemistry 1985, 24, 1953.