Alves, M. José

Duarte, Vera C. M.

Fortes, A. Gil

Micaelo, N. M.

Salgueiro, D. A. L.

Sousa, C. E. A.

Universidade do Minho: RepositoriUM

Synthesis of 1-azafagomine analog and 1-N-phenyl carboxamide 1-azafagomine containing erythrose units

Synthesis of 1-Azafagomine Analog and 1-N-Phenyl Carboxamide  1-Azafagomine Containing Erythrose Units  Salgueiro, D.A.L., Alves, M.J., Duarte, Vera C.M., Gil Fortes, A., Sousa, C.E.A, Micaelo, N.M. University of Minho, Chemistry Research Centre, Campus de Gualtar, 4700-057, Braga, Portugal  salgueiro.dany@gmail.com  The synthesis of iminosugars is an important topic in modern Organic Chemistry for their structures proved to be of great biological interest including as therapeutics. Iminosugars interfere with glycosidases, the natural carbohydrate processing enzymes, and with carbohydrate recognizing receptors spread in all living organisms. Some iminosugurs are part of the therapeutic arsenal against cancer, Gaucher, antiviral, and anti cancer diseases[1] The aim of this work was the synthesis of compound 1, an analogue of 1-azafagomine, and 2 a derivative of 1-N-phenyl carboxamide 1-azafagomine, recently showing a better inhibition power against α-glycosidase than 1-azafagomine itself.[2]  These compounds were selected by molecular modelling studies and will be tested against a series of α- and β-glycosidases. (Scheme 1) O OPhOTBSNN NOOPhO OPhOTBS N NN OOPhTBAFTHFO OPhOH N NN OOPhBiI3H2OOH OHOH N NN OOPhCF3CCH3ONaHCO3/oxoneOH OHOH N NN OOPhOH2SO4 H2OOH OHOH N NN OOPhOH OHOH OHOH HN NHOH OHNH2NH2O OOH N NN OOPhOPhO OOH N NHNHOPhPhOH OH BiI3H2OKOH OH OHOH N NHNHOPhOH OHScheme 12 1  Acknowledgements: We thanks to FCT (Project PTDC/QUI/67407/2006) QREN, COMPETE and POPH for financial support and to the Portuguese NMR Network RNRMN (Bruker Avance II 400). References: [1] Afarinkia, K.; Bahar, A. Tetrahedron: Asymmetry 16, 2005, 1239-1287. [2] Alves, M.J. et all, Unpublished results. 

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Synthesis of 1-azafagomine analog and 1-N-phenyl carboxamide 1-azafagomine containing erythrose units

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Universidade do Minho: RepositoriUM

Universidade do Minho: RepositoriUM