New syntheses towards C-glycosyl type glycomimetics

L. Somsák, Éva Bokor, László Juhász, Sándor Kun, L. Lázár, Éva Juhász-Tóth, M. Tóth

Research output: Contribution to journalArticle

Abstract

Glycomimetics are compounds that resemble carbohydrate molecules in their chemical structure and/or biological effect. A large variety of compounds can be designed and synthesized to get glycomimetics, however, C-glycosyl derivatives represent one of the most frequently studied subgroup. In the present survey syntheses of a range of five- and six membered C-glycopyranosyl heterocycles, anhydro-aldimine type compounds, exo-glycals, C-glycosyl styrenes, carbon-sulfur bonded oligosaccharide mimics are described. Some of the C-glycopyranosyl azoles, namely 1,2,4-triazoles and imidazoles belong to the most efficient glucose analog inhibitors of glycogen phosphorylase known to date. Biological studies revealed the therapeutical potential of such inhibitors. Other synthetic derivatives offer versatile possibilities to get further glycomimetics.

Original languageEnglish
JournalPure and Applied Chemistry
DOIs
Publication statusPublished - Jan 1 2019

Fingerprint

Styrenes
Imidazoles
Derivatives
Glycogen Phosphorylase
Azoles
Oligosaccharides
Carbohydrates
Sulfur
Glucose
Styrene
Carbon
Molecules
1,2,4-triazole
Glycogen

Keywords

  • anhydro-aldimines
  • C-glycosyl compounds
  • cross couplings
  • exo-glycals
  • glycogen phosphorylase
  • glycomimetics
  • ICS-29
  • inhibitors
  • thiol-ene additions
  • tosylhydrazones

ASJC Scopus subject areas

  • Chemistry(all)
  • Chemical Engineering(all)

Cite this

New syntheses towards C-glycosyl type glycomimetics. / Somsák, L.; Bokor, Éva; Juhász, László; Kun, Sándor; Lázár, L.; Juhász-Tóth, Éva; Tóth, M.

In: Pure and Applied Chemistry, 01.01.2019.

Research output: Contribution to journalArticle

Somsák, L. ; Bokor, Éva ; Juhász, László ; Kun, Sándor ; Lázár, L. ; Juhász-Tóth, Éva ; Tóth, M. / New syntheses towards C-glycosyl type glycomimetics. In: Pure and Applied Chemistry. 2019.
@article{697ee78e039543558a0249d968d70f72,
title = "New syntheses towards C-glycosyl type glycomimetics",
abstract = "Glycomimetics are compounds that resemble carbohydrate molecules in their chemical structure and/or biological effect. A large variety of compounds can be designed and synthesized to get glycomimetics, however, C-glycosyl derivatives represent one of the most frequently studied subgroup. In the present survey syntheses of a range of five- and six membered C-glycopyranosyl heterocycles, anhydro-aldimine type compounds, exo-glycals, C-glycosyl styrenes, carbon-sulfur bonded oligosaccharide mimics are described. Some of the C-glycopyranosyl azoles, namely 1,2,4-triazoles and imidazoles belong to the most efficient glucose analog inhibitors of glycogen phosphorylase known to date. Biological studies revealed the therapeutical potential of such inhibitors. Other synthetic derivatives offer versatile possibilities to get further glycomimetics.",
keywords = "anhydro-aldimines, C-glycosyl compounds, cross couplings, exo-glycals, glycogen phosphorylase, glycomimetics, ICS-29, inhibitors, thiol-ene additions, tosylhydrazones",
author = "L. Soms{\'a}k and {\'E}va Bokor and L{\'a}szl{\'o} Juh{\'a}sz and S{\'a}ndor Kun and L. L{\'a}z{\'a}r and {\'E}va Juh{\'a}sz-T{\'o}th and M. T{\'o}th",
year = "2019",
month = "1",
day = "1",
doi = "10.1515/pac-2019-0208",
language = "English",
journal = "Pure and Applied Chemistry",
issn = "0033-4545",
publisher = "IUPAC Secretariat",

}

TY - JOUR

T1 - New syntheses towards C-glycosyl type glycomimetics

AU - Somsák, L.

AU - Bokor, Éva

AU - Juhász, László

AU - Kun, Sándor

AU - Lázár, L.

AU - Juhász-Tóth, Éva

AU - Tóth, M.

PY - 2019/1/1

Y1 - 2019/1/1

N2 - Glycomimetics are compounds that resemble carbohydrate molecules in their chemical structure and/or biological effect. A large variety of compounds can be designed and synthesized to get glycomimetics, however, C-glycosyl derivatives represent one of the most frequently studied subgroup. In the present survey syntheses of a range of five- and six membered C-glycopyranosyl heterocycles, anhydro-aldimine type compounds, exo-glycals, C-glycosyl styrenes, carbon-sulfur bonded oligosaccharide mimics are described. Some of the C-glycopyranosyl azoles, namely 1,2,4-triazoles and imidazoles belong to the most efficient glucose analog inhibitors of glycogen phosphorylase known to date. Biological studies revealed the therapeutical potential of such inhibitors. Other synthetic derivatives offer versatile possibilities to get further glycomimetics.

AB - Glycomimetics are compounds that resemble carbohydrate molecules in their chemical structure and/or biological effect. A large variety of compounds can be designed and synthesized to get glycomimetics, however, C-glycosyl derivatives represent one of the most frequently studied subgroup. In the present survey syntheses of a range of five- and six membered C-glycopyranosyl heterocycles, anhydro-aldimine type compounds, exo-glycals, C-glycosyl styrenes, carbon-sulfur bonded oligosaccharide mimics are described. Some of the C-glycopyranosyl azoles, namely 1,2,4-triazoles and imidazoles belong to the most efficient glucose analog inhibitors of glycogen phosphorylase known to date. Biological studies revealed the therapeutical potential of such inhibitors. Other synthetic derivatives offer versatile possibilities to get further glycomimetics.

KW - anhydro-aldimines

KW - C-glycosyl compounds

KW - cross couplings

KW - exo-glycals

KW - glycogen phosphorylase

KW - glycomimetics

KW - ICS-29

KW - inhibitors

KW - thiol-ene additions

KW - tosylhydrazones

UR - http://www.scopus.com/inward/record.url?scp=85065389130&partnerID=8YFLogxK

UR - http://www.scopus.com/inward/citedby.url?scp=85065389130&partnerID=8YFLogxK

U2 - 10.1515/pac-2019-0208

DO - 10.1515/pac-2019-0208

M3 - Article

AN - SCOPUS:85065389130

JO - Pure and Applied Chemistry

JF - Pure and Applied Chemistry

SN - 0033-4545

ER -