Simple and efficient synthesis of triazole-based iminosugars with potential anti-glucosidase activity

Simple and efficient synthesis of triazole-based iminosugars with potential anti-glucosidase activity

Aragão-Leoneti, Valquiria; Carvalho, Ivone

Abstract:

Glucosidases are enzymes involved in key steps of the processing of oligosaccharides or glycoconjugates by cleaving O-glucose residues. Inhibitors of glucosidase are agents with high therapeutic potential since many of them show application for the treatment of diabetes, obesity, glycosphingolipid lysosomal storage disease, HIV infections, and tumors in general. Currently, there are three anti-glucosidases drugs: acarbose (1) (Precose®), miglitol (2) (Glyset®), and N-butyl-1- deoxynojirimycin (3) (Zavesca®) (Fig. 1), being these last two drugs N-substituted iminosugar. We herein present the synthesis of 1,2,3-triazole Nlinked iminosugars, from D-mannitol, with potential anti-glucosidase and anti-viral activities.

Glucosidases are enzymes involved in key steps of the processing of oligosaccharides or glycoconjugates by cleaving O-glucose residues. Inhibitors of glucosidase are agents with high therapeutic potential since many of them show application for the treatment of diabetes, obesity, glycosphingolipid lysosomal storage disease, HIV infections, and tumors in general. Currently, there are three anti-glucosidases drugs: acarbose (1) (Precose®), miglitol (2) (Glyset®), and N-butyl-1- deoxynojirimycin (3) (Zavesca®) (Fig. 1), being these last two drugs N-substituted iminosugar. We herein present the synthesis of 1,2,3-triazole Nlinked iminosugars, from D-mannitol, with potential anti-glucosidase and anti-viral activities.

Palavras-chave:

DOI: 10.5151/chempro-15bmos-BMOS2013_201382116258

Referências bibliográficas

• [1] 1 Melo, E. B.; Gomes, A. S.; Carvalho, I. Tetrahedron 2006, 62, 10277.
• [2] 2 Melo, E. B.; Carvalho, I. Quim. Nova 2006, 29, 840.
• [3] 3 Skinner, G. S.; Henderson, L. A.; Gustafson Jr., V. L. J. Am. Chem. Soc. 1958, 80, 3788.
• [4] 4 Golding, B. T.; Slaich, P. K.; Kennedy, G.; Bleasdale, C.; Watson, W. P. Chem. Res. Toxicol. 1996, 9, 147.

Como citar:

Aragão-Leoneti, Valquiria; Carvalho, Ivone; "Simple and efficient synthesis of triazole-based iminosugars with potential anti-glucosidase activity", p-59-59. In: In Blucher Chemistry Proceedings, São Paulo, v. 1, n. 2, Dezembro.2013. São Paulo: Blucher, 2013.
ISSN 23184043, DOI 10.5151/chempro-15bmos-BMOS2013_201382116258