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

Mária Petrušová, Hana Smrtičová, Božena Pribulová, Silvia Vlčková, Iveta Uhliariková, T. Docsa, L. Somsák, Ladislav Petruš

Research output: Contribution to journalArticle

4 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 (IC 50=125 μM).

Original languageEnglish
JournalTetrahedron
DOIs
Publication statusAccepted/In press - Oct 22 2015

Fingerprint

Imidazoles
Methylamines
Phenylglyoxal
Phosphorylase b
Glyoxal
Derivatives
Glycogen Phosphorylase
Indium
Catalysis
Formaldehyde
Methanol
Muscle
Chlorides
Rabbits
Muscles
Temperature
imidazole
benzil

Keywords

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

ASJC Scopus subject areas

  • Biochemistry
  • Organic Chemistry
  • Drug Discovery

Cite this

Petrušová, M., Smrtičová, H., Pribulová, B., Vlčková, S., Uhliariková, I., Docsa, T., ... Petruš, L. (Accepted/In press). One pot InCl3-catalyzed synthesis of 1-glycosylmethyl-1H-imidazoles. Tetrahedron. https://doi.org/10.1016/j.tet.2016.03.010

One pot InCl3-catalyzed synthesis of 1-glycosylmethyl-1H-imidazoles. / Petrušová, Mária; Smrtičová, Hana; Pribulová, Božena; Vlčková, Silvia; Uhliariková, Iveta; Docsa, T.; Somsák, L.; Petruš, Ladislav.

In: Tetrahedron, 22.10.2015.

Research output: Contribution to journalArticle

Petrušová, M, Smrtičová, H, Pribulová, B, Vlčková, S, Uhliariková, I, Docsa, T, Somsák, L & Petruš, L 2015, 'One pot InCl3-catalyzed synthesis of 1-glycosylmethyl-1H-imidazoles', Tetrahedron. https://doi.org/10.1016/j.tet.2016.03.010
Petrušová M, Smrtičová H, Pribulová B, Vlčková S, Uhliariková I, Docsa T et al. One pot InCl3-catalyzed synthesis of 1-glycosylmethyl-1H-imidazoles. Tetrahedron. 2015 Oct 22. https://doi.org/10.1016/j.tet.2016.03.010
Petrušová, Mária ; Smrtičová, Hana ; Pribulová, Božena ; Vlčková, Silvia ; Uhliariková, Iveta ; Docsa, T. ; Somsák, L. ; Petruš, Ladislav. / One pot InCl3-catalyzed synthesis of 1-glycosylmethyl-1H-imidazoles. In: Tetrahedron. 2015.
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