One pot InCl3-catalyzed synthesis of 1-glycosylmethyl-1H-imidazoles

Mária Petrušová, Hana Smrtičová, Božena Pribulová, Silvia Vlčková, Iveta Uhliariková, Tibor Docsa, László Somsák, Ladislav Petruš

Research output: Contribution to journalArticle

6 Citations (Scopus)

Abstract

A series of 1-glycosylmethyl-4,5-diphenyl-1H-imidazoles with six different glycosyls were obtained in 48-55% yields from the multicomponent reaction of the corresponding C-glycosyl methylamines, formaldehyde, benzil, and ammonium acetate under catalysis with indium(III) chloride in methanol at ambient temperature. Starting with C-β-d-glucopyranosyl or C-β-d-galactopyranosyl methylamines, the procedure also was examined with phenylglyoxal or glyoxal instead of benzil, and the pertinent 1-β-d-glycopyranosylmethyl-4-phenyl-1H-imidazole and -5-phenyl-1H-imidazole or 1-β-d-glycopyranosylmethyl-1H-imidazole derivatives were prepared and isolated. Of four differently 4- and 5-substituted 1-(β-d-glucopyranosylmethyl)-1H-imidazoles, only the 5-phenyl derivative exhibited a weak inhibition of rabbit muscle glycogen phosphorylase b (IC50=125 μM).

Original languageEnglish
Pages (from-to)2116-2121
Number of pages6
JournalTetrahedron
Volume72
Issue number17
DOIs
Publication statusPublished - Apr 28 2016

Keywords

  • 1-Glycosylmethyl-1H-imidazoles
  • C-Glycosyl methylamines
  • Indium(III) chloride catalysis
  • Multicomponent reaction
  • Rabbit muscle glycogen phosphorylase inhibition

ASJC Scopus subject areas

  • Biochemistry
  • Drug Discovery
  • Organic Chemistry

Fingerprint Dive into the research topics of 'One pot InCl<sub>3</sub>-catalyzed synthesis of 1-glycosylmethyl-1H-imidazoles'. Together they form a unique fingerprint.

  • Cite this

    Petrušová, M., Smrtičová, H., Pribulová, B., Vlčková, S., Uhliariková, I., Docsa, T., Somsák, L., & Petruš, L. (2016). One pot InCl3-catalyzed synthesis of 1-glycosylmethyl-1H-imidazoles. Tetrahedron, 72(17), 2116-2121. https://doi.org/10.1016/j.tet.2016.03.010