The first general synthesis of 2-C-(β-d-glycopyranosyl)pyrimidines and their evaluation as inhibitors of some glycoenzymes

Eszter Szennyes, Eva Bokor, Peter Langer, Gyöngyi Gyémánt, Tibor Docsa, Ádám Sipos, László Somsák

Research output: Contribution to journalArticle

4 Citations (Scopus)

Abstract

A systematic study was performed on the preparation of unknown 2-C-(β-d-glucopyranosyl)pyrimidines. Pinner type cyclisation of O-perbenzylated C-(β-d-glucopyranosyl)formamidine with β-ketoesters, dimethyl malonate, and β-diketone derived α,β-unsaturated β-chloroketones followed by catalytic hydrogenation resulted in various substituted 2-C-(β-d-glucopyranosyl)-pyrimidin-4(3H)-ones, and 2-C-(β-d-glucopyranosyl)-4,6-disubstituted-pyrimidines, respectively, in moderate to good yields. The above pyrimidine derivatives were also obtained by ring closure of the unprotected C-(β-d-glucopyranosyl)formamidine with the same 1,3-dielectrophiles. In addition, a continuous one-pot three-step procedure starting from O-peracylated d-glycopyranosyl cyanides was also elaborated to give representatives of the aforementioned pyrimidines with various sugar configurations in acceptable to excellent overall yields (25-94%). Due to the versatility of the applied 1,3-dielectrophiles, these synthetic routes represent the first expansible method to obtain the target compounds. The new C-glycopyranosyl pyrimidines showed moderate inhibition against α-glucosidase and β-galactosidase enzymes, had, however, no activity against glycogen phosphorylase. The obtained molecule library is ready for further biological testing.

Original languageEnglish
Pages (from-to)17439-17446
Number of pages8
JournalNew Journal of Chemistry
Volume42
Issue number21
DOIs
Publication statusPublished - Jan 1 2018

ASJC Scopus subject areas

  • Catalysis
  • Chemistry(all)
  • Materials Chemistry

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