Synthesis of novel C-glucopyranosyl heterocycles for the inhibition of sodium-dependent glucose cotransporter 2

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Mini symposium: Glycobiology at the LUMC and beyond

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Synthesis of novel C-glucopyranosyl heterocycles for the inhibition of sodium-dependent glucose cotransporter 2

Sándor Kun 1 , Eszter Szennyes 1 , Éva Bokor 1 , Nikolett Éva Hajnal 1 , Ádám Sipos 2 , Tibor Docsa 2, László Somsák 1

1 Department Of Organic Chemistry, University Of Debrecen, Debrecen, Hungary, 2 Department of Medical Chemistry, Medical and Health Science Centre, University of Debrecen, Debrecen, Hungary

Sodium-glucose cotransporter 2 (SGLT2) inhibitors belong to a novel class of oral anti-hyperglycemic agents that reduce plasma glucose concentrations by the inhibition of glucose reabsorption in the kidney thereby inducing glucosuria.[1,2]

Marketed SGLT2 inhibitors [1] also called gliflozins are C-glycosyl derivatives having diaryl methane type aglycone (1), in which the second aryl moiety can be a heteroaromatic ring (thiophene or benzothiophene), as well. Several promising inhibitors were found among glucose derivatives wherein the first aryl unit was replaced by a hetrarene ring such as thiophene, pyrrole, thiazole, pyridine, pyrazine and pyridazine.[2] In connection with this, synthesis of similar arylmethyl substituted C-β-D-glucopyranosyl heterocycles (i.e. pyrimidines (2a) and oxadiazoles (2b,c)) was envisaged in order to broaden the structure-activity relationship studies of such type of SGLT2 inhibitors.

In the presentation the syntheses of 2a-c and preliminary results of SGLT2 inhibition will be reported.

Aguillón, A. R.; Mascarello, A.; Segretti, N. D.; de Azevedo, H. F. Z. C.; Guimaraes, R. W.; Miranda, L. S. M.; de Souza. R. O. M. A. Synthetic strategies toward SGLT2 inhibitors. Org. Process Res. Dev. 2018, 22, 467-488.

Bokor, É.; Kun, S.; Goyard, D.; Tóth, M.; Praly, J.-P.; Vidal, S.; Somsák, L. C-Glycopyranosyl arenes and hetarenes: synthetic methods and bioactivity focused on antidiabetic potential. Chem. Rev. 2017, 117, 1687-1764.

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