Literature DB >> 24900719

C-Glucopyranosyl-1,2,4-triazoles As New Potent Inhibitors of Glycogen Phosphorylase.

Eva Bokor1, Tibor Docsa2, Pál Gergely2, László Somsák1.   

Abstract

Glycogen phosphorylase inhibitors are considered as potential antidiabetic agents. 3-(β-d-Glucopyranosyl)-5-substituted-1,2,4-triazoles were prepared by acylation of O-perbenzoylated N (1)-tosyl-C-β-d-glucopyranosyl formamidrazone and subsequent removal of the protecting groups. The best inhibitor was 3-(β-d-glucopyranosyl)-5-(2-naphthyl)-1,2,4-triazole (K i = 0.41 μM against rabbit muscle glycogen phosphorylase b).

Entities:  

Keywords:  1,2,4-Triazole; C-glucopyranosyl derivative; bioisoster; glycogen phosphorylase; inhibitor

Year:  2013        PMID： 24900719      PMCID： PMC4027562          DOI： 10.1021/ml4001529

Source DB:  PubMed          Journal:  ACS Med Chem Lett        ISSN： 1948-5875            Impact factor:   4.345


  24 in total

Review 1.  Bioisosterism: a useful strategy for molecular modification and drug design.

Authors:  Lídia Moreira Lima; Eliezer J Barreiro
Journal:  Curr Med Chem       Date:  2005       Impact factor: 4.530

Review 2.  New inhibitors of glycogen phosphorylase as potential antidiabetic agents.

Authors:  L Somsák; K Czifrák; M Tóth; E Bokor; E D Chrysina; K-M Alexacou; J M Hayes; C Tiraidis; E Lazoura; D D Leonidas; S E Zographos; N G Oikonomakos
Journal:  Curr Med Chem       Date:  2008       Impact factor: 4.530

Review 3.  From structure--based to knowledge--based drug design through x-ray protein crystallography: sketching glycogen phosphorylase binding sites.

Authors:  E D Chrysina; A Chajistamatiou; M Chegkazi
Journal:  Curr Med Chem       Date:  2011       Impact factor: 4.530

4.  Synthesis of heterocyclic N-(β-D-glucopyranosyl)carboxamides for inhibition of glycogen phosphorylase.

Authors:  Bálint Kónya; Tibor Docsa; Pál Gergely; László Somsák
Journal:  Carbohydr Res       Date:  2012-01-31       Impact factor: 2.104

Review 5.  Glycogen phosphorylase inhibitors.

Authors:  Brad R Henke; Steven M Sparks
Journal:  Mini Rev Med Chem       Date:  2006-08       Impact factor: 3.862

6.  Effect of glucopyranosylidene-spiro-thiohydantoin on glycogen metabolism in liver tissues of streptozotocin-induced and obese diabetic rats.

Authors:  Tibor Docsa; Katalin Czifrák; Csaba Hüse; László Somsák; Pál Gergely
Journal:  Mol Med Rep       Date:  2011-03-22       Impact factor: 2.952

7.  Synthesis of 1,2,4-triazole C-nucleosides from hydrazonyl chlorides and nitriles.

Authors:  Najim A Al-Masoudi; Yaseen A Al-Soud; Ibrahim A I Ali
Journal:  Nucleosides Nucleotides Nucleic Acids       Date:  2007       Impact factor: 1.381

Review 8.  Potential drug targets and progress towards pharmacologic inhibition of hepatic glucose production.

Authors:  R Kurukulasuriya; J T Link; D J Madar; Z Pei; S J Richards; J J Rohde; A J Souers; B G Szczepankiewicz
Journal:  Curr Med Chem       Date:  2003-01       Impact factor: 4.530

9.  Synthesis and structure-activity relationships of C-glycosylated oxadiazoles as inhibitors of glycogen phosphorylase.

Authors:  Marietta Tóth; Sándor Kun; Eva Bokor; Mahmoud Benltifa; Gaylord Tallec; Sébastien Vidal; Tibor Docsa; Pál Gergely; László Somsák; Jean-Pierre Praly
Journal:  Bioorg Med Chem       Date:  2009-04-23       Impact factor: 3.641

Review 10.  New hepatic targets for glycaemic control in diabetes.

Authors:  Loranne Agius
Journal:  Best Pract Res Clin Endocrinol Metab       Date:  2007-12       Impact factor: 4.690
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  7 in total

1.  Glycogen phosphorylase inhibition improves beta cell function.

Authors:  Lilla Nagy; Judit Márton; András Vida; Gréta Kis; Éva Bokor; Sándor Kun; Mónika Gönczi; Tibor Docsa; Attila Tóth; Miklós Antal; Pál Gergely; Balázs Csóka; Pal Pacher; László Somsák; Péter Bai
Journal:  Br J Pharmacol       Date:  2017-06-18       Impact factor: 8.739

2.  4(5)-Aryl-2-C-glucopyranosyl-imidazoles as New Nanomolar Glucose Analogue Inhibitors of Glycogen Phosphorylase.

Authors:  Éva Bokor; Sándor Kun; Tibor Docsa; Pál Gergely; László Somsák
Journal:  ACS Med Chem Lett       Date:  2015-10-19       Impact factor: 4.345

3.  Organocatalyzed preparation of 1,4,5-trisubstituted-glycosyl-1,2,3-triazole derivatives.

Authors:  Monalisa Kundu; Ishani Bhaumik; Anup Kumar Misra
Journal:  Glycoconj J       Date:  2019-07-05       Impact factor: 2.916

4.  3-Glucosylated 5-amino-1,2,4-oxadiazoles: synthesis and evaluation as glycogen phosphorylase inhibitors.

Authors:  Marion Donnier-Maréchal; David Goyard; Vincent Folliard; Tibor Docsa; Pal Gergely; Jean-Pierre Praly; Sébastien Vidal
Journal:  Beilstein J Org Chem       Date:  2015-04-17       Impact factor: 2.883

5.  Dual-Target Compounds against Type 2 Diabetes Mellitus: Proof of Concept for Sodium Dependent Glucose Transporter (SGLT) and Glycogen Phosphorylase (GP) Inhibitors.

Authors:  Ádám Sipos; Eszter Szennyes; Nikolett Éva Hajnal; Sándor Kun; Katalin E Szabó; Karen Uray; László Somsák; Tibor Docsa; Éva Bokor
Journal:  Pharmaceuticals (Basel)       Date:  2021-04-15

Review 6.  Synthesis methods of 1,2,3-/1,2,4-triazoles: A review.

Authors:  Jinlian Dai; Sen Tian; Xueqing Yang; Zongliang Liu
Journal:  Front Chem       Date:  2022-09-26       Impact factor: 5.545

7.  Synthesis of New C- and N-β-d-Glucopyranosyl Derivatives of Imidazole, 1,2,3-Triazole and Tetrazole, and Their Evaluation as Inhibitors of Glycogen Phosphorylase.

Authors:  Sándor Kun; Éva Bokor; Ádám Sipos; Tibor Docsa; László Somsák
Journal:  Molecules       Date:  2018-03-15       Impact factor: 4.411
  7 in total

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