{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2026,4,5]],"date-time":"2026-04-05T06:58:02Z","timestamp":1775372282992,"version":"3.50.1"},"reference-count":67,"publisher":"MDPI AG","issue":"3","license":[{"start":{"date-parts":[[2018,3,15]],"date-time":"2018-03-15T00:00:00Z","timestamp":1521072000000},"content-version":"vor","delay-in-days":0,"URL":"https:\/\/creativecommons.org\/licenses\/by\/4.0\/"}],"funder":[{"name":"National Research, Innovation and Development Office of Hungary","award":["PD 121406"],"award-info":[{"award-number":["PD 121406"]}]},{"DOI":"10.13039\/501100008530","name":"European Regional Development Fund","doi-asserted-by":"publisher","award":["GINOP-2.3.2-15-2016-00008"],"award-info":[{"award-number":["GINOP-2.3.2-15-2016-00008"]}],"id":[{"id":"10.13039\/501100008530","id-type":"DOI","asserted-by":"publisher"}]},{"DOI":"10.13039\/501100008530","name":"European Regional Development Fund","doi-asserted-by":"publisher","award":["GINOP-2.3.3-15-2016-00004"],"award-info":[{"award-number":["GINOP-2.3.3-15-2016-00004"]}],"id":[{"id":"10.13039\/501100008530","id-type":"DOI","asserted-by":"publisher"}]}],"content-domain":{"domain":[],"crossmark-restriction":false},"short-container-title":["Molecules"],"abstract":"<jats:p>The aim of the present study was to broaden the structure-activity relationships of C- and N-\u03b2-d-glucopyranosyl azole type inhibitors of glycogen phosphorylase. 1-Aryl-4-\u03b2-d-gluco-pyranosyl-1,2,3-triazoles were prepared by copper catalyzed azide-alkyne cycloadditions between O-perbenzylated or O-peracetylated \u03b2-d-glucopyranosyl ethynes and aryl azides. 1-\u03b2-d-Gluco-pyranosyl-4-phenyl imidazole was obtained in a glycosylation of 4(5)-phenylimidazole with O-peracetylated \u03b1-d-glucopyranosyl bromide. C-\u03b2-d-Glucopyranosyl-N-substituted-tetrazoles were synthesized by alkylation\/arylation of O-perbenzoylated 5-\u03b2-d-glucopyranosyl-tetrazole or from a 2,6-anhydroheptose tosylhydrazone and arenediazonium salts. 5-Substituted tetrazoles were glycosylated by O-peracetylated \u03b1-d-glucopyranosyl bromide to give N-\u03b2-d-glucopyranosyl-C-substituted-tetrazoles. Standard deprotections gave test compounds which were assayed against rabbit muscle glycogen phosphorylase b. Most of the compounds proved inactive, the best inhibitor was 2-\u03b2-d-glucopyranosyl-5-phenyltetrazole (IC50 600 \u03bcM). These studies extended the structure-activity relationships of \u03b2-d-glucopyranosyl azole type inhibitors and revealed the extreme sensitivity of such type of inhibitors towards the structure of the azole moiety.<\/jats:p>","DOI":"10.3390\/molecules23030666","type":"journal-article","created":{"date-parts":[[2018,3,15]],"date-time":"2018-03-15T16:07:17Z","timestamp":1521130037000},"page":"666","update-policy":"https:\/\/doi.org\/10.3390\/mdpi_crossmark_policy","source":"Crossref","is-referenced-by-count":14,"title":["Synthesis of New C- and N-\u03b2-d-Glucopyranosyl Derivatives of Imidazole, 1,2,3-Triazole and Tetrazole, and Their Evaluation as Inhibitors of Glycogen Phosphorylase"],"prefix":"10.3390","volume":"23","author":[{"ORCID":"https:\/\/orcid.org\/0000-0002-0111-390X","authenticated-orcid":false,"given":"S\u00e1ndor","family":"Kun","sequence":"first","affiliation":[{"name":"Department of Organic Chemistry, University of Debrecen, P.O. Box 400, H-4002 Debrecen, Hungary"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"\u00c9va","family":"Bokor","sequence":"additional","affiliation":[{"name":"Department of Organic Chemistry, University of Debrecen, P.O. Box 400, H-4002 Debrecen, Hungary"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"\u00c1d\u00e1m","family":"Sipos","sequence":"additional","affiliation":[{"name":"Department of Medical Chemistry, Faculty of Medicine, University of Debrecen, Egyetem t\u00e9r 1, H-4032 Debrecen, Hungary"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Tibor","family":"Docsa","sequence":"additional","affiliation":[{"name":"Department of Medical Chemistry, Faculty of Medicine, University of Debrecen, Egyetem t\u00e9r 1, H-4032 Debrecen, Hungary"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-9103-9845","authenticated-orcid":false,"given":"L\u00e1szl\u00f3","family":"Soms\u00e1k","sequence":"additional","affiliation":[{"name":"Department of Organic Chemistry, University of Debrecen, P.O. Box 400, H-4002 Debrecen, Hungary"}],"role":[{"role":"author","vocabulary":"crossref"}]}],"member":"1968","published-online":{"date-parts":[[2018,3,15]]},"reference":[{"key":"ref_1","doi-asserted-by":"crossref","first-page":"1102","DOI":"10.2174\/1389557511009011102","article-title":"Inhibition of Glycogen Phosphorylase in the Context of Type 2 Diabetes, with Focus on Recent Inhibitors Bound at the Active Site","volume":"10","author":"Praly","year":"2010","journal-title":"Mini-Rev. Med. Chem."},{"key":"ref_2","first-page":"211","article-title":"Glucose derived inhibitors of glycogen phosphorylase","volume":"14","year":"2011","journal-title":"Comptes Rendus Chim."},{"key":"ref_3","doi-asserted-by":"crossref","first-page":"471","DOI":"10.1007\/s11101-014-9360-6","article-title":"Natural products and their derivatives as inhibitors of glycogen phosphorylase: Potential treatment for type 2 diabetes","volume":"13","author":"Hayes","year":"2014","journal-title":"Phytochem. 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