Our previous reports on the synthesis of α-glucosidase inhibitors [1-2] stimulated us to develop alternative synthetic strategy for new analogs by incorporation of additional functional groups enhancing the inhibitory response. One of the possible bioisoster functional group are selenoglycosides or selenoureas. The seleno-linked deoxy-sugars families [3] are common components of many glucosidase inhibitors [4] as potential antidiabetics. Our earlier synthetic strategy was based on previously well-established chemistry of isoselenocyanates [5-6] developed in our laboratories. The current studies are devoted to the stereoselective functionalization of the anomeric position at C-1 via the reactions of fully protected pivaloylglycosylamines with fluorinated aromatic isoselenocyanates [7]. This approach successfully produces the new representatives of this new class of inhibitors in 78-85% yield. The stereoselectivity of the functionalization and the spectroscopic data 1H and 13C NMR of the above Se-linked prototypes, together with their glucosidase inhibitory characteristics will be discussed in details. 1. Z. J. Witczak, D. Boryczewski, Bioorganic & Med. Chem. Lett., 8, 3265-3268, 1998. 2. Z. J. Witczak, R. Chhabra, H. Chen, X-Q. Xie, Carbohydr.Res.301, 167-175, 1997. 3. Z. J. Witczak, R.L. Whistler, Heterocycles, 19, 1719-1734, 1982. 4. A. Ghavami, B.D. Johnston, B. M. Pinto, J. Org. Chem., 66, 2312–2317, 2001. 5. Z. J. Witczak, Tetrahedron, 41, 4781-4785, 1985. 6. Z. J. Witczak, S. Czernecki, Adv.Carb.Chem. Biochem. 53, 143-199, 1998. 7. O. Lopez, S. Maza, V. Ulgar, I. Maya, J.G. Fernandez-Bolanos, Tetrahedron, 65, 2556-2566, 2009. Acknwledgement: G. M. acknowledges the National Science Center (Cracow, Poland) for financial support within the OPUS project (2014/13/B/ST5/04004)

Synthesis of fluorinated glucopyranosyl selenoureas as new generation of  glucosidase inhibitors

251st National Meeting (2016)

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