Synthesis of 2-(β-d-glucopyranosylamino)-5-substituted-1,3,4- oxadiazoles for inhibition of glycogen phosphorylase

M. Tóth, Béla Szocs, Tímea Kaszás, T. Docsa, P. Gergely, L. Somsák

Research output: Contribution to journalArticle

7 Citations (Scopus)

Abstract

Aromatic aldehyde 4-(2,3,4,6-tetra-O-acetyl-β-d-glucopyranosyl) semicarbazones were synthesized by the addition of different hydrazones onto O-peracetylated β-d-glucopyranosyl isocyanate. Oxidative transformations of these precursors gave O-protected 2-(β-d-glucopyranosylamino)-5- substituted-1,3,4-oxadiazoles. Removal of the O-acetyl protecting groups under Zemplén conditions gave test compounds to show low micromolar inhibition against rabbit muscle glycogen phosphorylase b. Best inhibitors of these series were 4-(β-d-glucopyranosyl)semicarbazones of 4-nitrobenzaldehyde (K i = 4.5 μM), 2-naphthaldehyde (Ki = 5.5 μM) and 2-(β-d-glucopyranosylamino)-5-(4-methylphenyl)-1,3,4-oxadiazole (K i = 12 μM).

Original languageEnglish
Pages (from-to)196-204
Number of pages9
JournalCarbohydrate Research
Volume381
DOIs
Publication statusPublished - 2013

Fingerprint

Semicarbazones
Glycogen Phosphorylase
4-nitrobenzaldehyde
Phosphorylase b
Isocyanates
Hydrazones
Aldehydes
Muscle
Rabbits
Muscles
1,3,4-oxadiazole

Keywords

  • 1,3,4-Oxadiazole
  • Glycogen phosphorylase
  • Inhibitor
  • Semicarbazone
  • β-d-Glucopyranosyl derivatives

ASJC Scopus subject areas

  • Biochemistry
  • Analytical Chemistry
  • Organic Chemistry

Cite this

@article{54c0b6e98cdc4ac8920457166087fde4,
title = "Synthesis of 2-(β-d-glucopyranosylamino)-5-substituted-1,3,4- oxadiazoles for inhibition of glycogen phosphorylase",
abstract = "Aromatic aldehyde 4-(2,3,4,6-tetra-O-acetyl-β-d-glucopyranosyl) semicarbazones were synthesized by the addition of different hydrazones onto O-peracetylated β-d-glucopyranosyl isocyanate. Oxidative transformations of these precursors gave O-protected 2-(β-d-glucopyranosylamino)-5- substituted-1,3,4-oxadiazoles. Removal of the O-acetyl protecting groups under Zempl{\'e}n conditions gave test compounds to show low micromolar inhibition against rabbit muscle glycogen phosphorylase b. Best inhibitors of these series were 4-(β-d-glucopyranosyl)semicarbazones of 4-nitrobenzaldehyde (K i = 4.5 μM), 2-naphthaldehyde (Ki = 5.5 μM) and 2-(β-d-glucopyranosylamino)-5-(4-methylphenyl)-1,3,4-oxadiazole (K i = 12 μM).",
keywords = "1,3,4-Oxadiazole, Glycogen phosphorylase, Inhibitor, Semicarbazone, β-d-Glucopyranosyl derivatives",
author = "M. T{\'o}th and B{\'e}la Szocs and T{\'i}mea Kasz{\'a}s and T. Docsa and P. Gergely and L. Soms{\'a}k",
year = "2013",
doi = "10.1016/j.carres.2013.04.025",
language = "English",
volume = "381",
pages = "196--204",
journal = "Carbohydrate Research",
issn = "0008-6215",
publisher = "Elsevier BV",

}

TY - JOUR

T1 - Synthesis of 2-(β-d-glucopyranosylamino)-5-substituted-1,3,4- oxadiazoles for inhibition of glycogen phosphorylase

AU - Tóth, M.

AU - Szocs, Béla

AU - Kaszás, Tímea

AU - Docsa, T.

AU - Gergely, P.

AU - Somsák, L.

PY - 2013

Y1 - 2013

N2 - Aromatic aldehyde 4-(2,3,4,6-tetra-O-acetyl-β-d-glucopyranosyl) semicarbazones were synthesized by the addition of different hydrazones onto O-peracetylated β-d-glucopyranosyl isocyanate. Oxidative transformations of these precursors gave O-protected 2-(β-d-glucopyranosylamino)-5- substituted-1,3,4-oxadiazoles. Removal of the O-acetyl protecting groups under Zemplén conditions gave test compounds to show low micromolar inhibition against rabbit muscle glycogen phosphorylase b. Best inhibitors of these series were 4-(β-d-glucopyranosyl)semicarbazones of 4-nitrobenzaldehyde (K i = 4.5 μM), 2-naphthaldehyde (Ki = 5.5 μM) and 2-(β-d-glucopyranosylamino)-5-(4-methylphenyl)-1,3,4-oxadiazole (K i = 12 μM).

AB - Aromatic aldehyde 4-(2,3,4,6-tetra-O-acetyl-β-d-glucopyranosyl) semicarbazones were synthesized by the addition of different hydrazones onto O-peracetylated β-d-glucopyranosyl isocyanate. Oxidative transformations of these precursors gave O-protected 2-(β-d-glucopyranosylamino)-5- substituted-1,3,4-oxadiazoles. Removal of the O-acetyl protecting groups under Zemplén conditions gave test compounds to show low micromolar inhibition against rabbit muscle glycogen phosphorylase b. Best inhibitors of these series were 4-(β-d-glucopyranosyl)semicarbazones of 4-nitrobenzaldehyde (K i = 4.5 μM), 2-naphthaldehyde (Ki = 5.5 μM) and 2-(β-d-glucopyranosylamino)-5-(4-methylphenyl)-1,3,4-oxadiazole (K i = 12 μM).

KW - 1,3,4-Oxadiazole

KW - Glycogen phosphorylase

KW - Inhibitor

KW - Semicarbazone

KW - β-d-Glucopyranosyl derivatives

UR - http://www.scopus.com/inward/record.url?scp=84886718753&partnerID=8YFLogxK

UR - http://www.scopus.com/inward/citedby.url?scp=84886718753&partnerID=8YFLogxK

U2 - 10.1016/j.carres.2013.04.025

DO - 10.1016/j.carres.2013.04.025

M3 - Article

C2 - 23673237

AN - SCOPUS:84886718753

VL - 381

SP - 196

EP - 204

JO - Carbohydrate Research

JF - Carbohydrate Research

SN - 0008-6215

ER -