Synthesis of New Series of 2-<i>C</i>-(β-D-glucopyranosyl)-Pyrimidines and Their Evaluation as Inhibitors of Some Glycoenzymes
Despite the substantial interest in <i>C</i>-glycosyl heterocycles as mimetics of biologically active native glycans, the appearance of <i>C</i>-glycopyranosyl derivatives of six-membered heterocycles, both in synthetic and biological contexts, is rather scarce. As part of ou...
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doaj-5c36d63b8cf24776bb811a81f106e6082020-11-25T02:05:44ZengMDPI AGMolecules1420-30492020-02-0125370110.3390/molecules25030701molecules25030701Synthesis of New Series of 2-<i>C</i>-(β-D-glucopyranosyl)-Pyrimidines and Their Evaluation as Inhibitors of Some GlycoenzymesEszter Szennyes0Gyöngyi Gyémánt1László Somsák2Éva Bokor3Department of Organic Chemistry, University of Debrecen, P.O. Box 400, H-4002 Debrecen, HungaryDepartment of Inorganic and Analytical Chemistry, University of Debrecen, P.O. Box 400, H-4002 Debrecen, HungaryDepartment of Organic Chemistry, University of Debrecen, P.O. Box 400, H-4002 Debrecen, HungaryDepartment of Organic Chemistry, University of Debrecen, P.O. Box 400, H-4002 Debrecen, HungaryDespite the substantial interest in <i>C</i>-glycosyl heterocycles as mimetics of biologically active native glycans, the appearance of <i>C</i>-glycopyranosyl derivatives of six-membered heterocycles, both in synthetic and biological contexts, is rather scarce. As part of our ongoing research program aimed at preparing hitherto barely known 2-<i>C</i>-glycopyranosyl pyrimidines, the goal of the present study was to synthesize new 5-mono- and multiply substituted derivatives of this compound class. Thus, 2-<i>C</i>-(β-D-glucopyranosyl)-5,6-disubstituted-pyrimidin-4(3<i>H</i>)-ones and 4-amino-2-<i>C</i>-(β-D-glucopyranosyl)-5,6-disubstituted-pyrimidines were prepared by base-mediated cyclocondensations of <i>O</i>-perbenzylated and <i>O</i>-unprotected <i>C</i>-(β-D-glucopyranosyl) formamidine hydrochlorides with methylenemalonic acid derivatives. The 2-<i>C</i>-(β-D-glucopyranosyl)-5-substituted-pyrimidines were obtained from the same amidine precursors upon treatment with vinamidinium salts. The deprotected derivatives of these pyrimidines were tested as inhibitors of some glycoenzymes. None of them showed inhibitory activity towards glycogen phosphorylase and α- and β-glucosidase enzymes, but some members of the sets exhibited moderate inhibition against bovine liver β-galactosidase.https://www.mdpi.com/1420-3049/25/3/701<i>c</i>-glucopyranosyl derivativepyrimidineamidineglycoenzymeinhibitor |
collection |
DOAJ |
language |
English |
format |
Article |
sources |
DOAJ |
author |
Eszter Szennyes Gyöngyi Gyémánt László Somsák Éva Bokor |
spellingShingle |
Eszter Szennyes Gyöngyi Gyémánt László Somsák Éva Bokor Synthesis of New Series of 2-<i>C</i>-(β-D-glucopyranosyl)-Pyrimidines and Their Evaluation as Inhibitors of Some Glycoenzymes Molecules <i>c</i>-glucopyranosyl derivative pyrimidine amidine glycoenzyme inhibitor |
author_facet |
Eszter Szennyes Gyöngyi Gyémánt László Somsák Éva Bokor |
author_sort |
Eszter Szennyes |
title |
Synthesis of New Series of 2-<i>C</i>-(β-D-glucopyranosyl)-Pyrimidines and Their Evaluation as Inhibitors of Some Glycoenzymes |
title_short |
Synthesis of New Series of 2-<i>C</i>-(β-D-glucopyranosyl)-Pyrimidines and Their Evaluation as Inhibitors of Some Glycoenzymes |
title_full |
Synthesis of New Series of 2-<i>C</i>-(β-D-glucopyranosyl)-Pyrimidines and Their Evaluation as Inhibitors of Some Glycoenzymes |
title_fullStr |
Synthesis of New Series of 2-<i>C</i>-(β-D-glucopyranosyl)-Pyrimidines and Their Evaluation as Inhibitors of Some Glycoenzymes |
title_full_unstemmed |
Synthesis of New Series of 2-<i>C</i>-(β-D-glucopyranosyl)-Pyrimidines and Their Evaluation as Inhibitors of Some Glycoenzymes |
title_sort |
synthesis of new series of 2-<i>c</i>-(β-d-glucopyranosyl)-pyrimidines and their evaluation as inhibitors of some glycoenzymes |
publisher |
MDPI AG |
series |
Molecules |
issn |
1420-3049 |
publishDate |
2020-02-01 |
description |
Despite the substantial interest in <i>C</i>-glycosyl heterocycles as mimetics of biologically active native glycans, the appearance of <i>C</i>-glycopyranosyl derivatives of six-membered heterocycles, both in synthetic and biological contexts, is rather scarce. As part of our ongoing research program aimed at preparing hitherto barely known 2-<i>C</i>-glycopyranosyl pyrimidines, the goal of the present study was to synthesize new 5-mono- and multiply substituted derivatives of this compound class. Thus, 2-<i>C</i>-(β-D-glucopyranosyl)-5,6-disubstituted-pyrimidin-4(3<i>H</i>)-ones and 4-amino-2-<i>C</i>-(β-D-glucopyranosyl)-5,6-disubstituted-pyrimidines were prepared by base-mediated cyclocondensations of <i>O</i>-perbenzylated and <i>O</i>-unprotected <i>C</i>-(β-D-glucopyranosyl) formamidine hydrochlorides with methylenemalonic acid derivatives. The 2-<i>C</i>-(β-D-glucopyranosyl)-5-substituted-pyrimidines were obtained from the same amidine precursors upon treatment with vinamidinium salts. The deprotected derivatives of these pyrimidines were tested as inhibitors of some glycoenzymes. None of them showed inhibitory activity towards glycogen phosphorylase and α- and β-glucosidase enzymes, but some members of the sets exhibited moderate inhibition against bovine liver β-galactosidase. |
topic |
<i>c</i>-glucopyranosyl derivative pyrimidine amidine glycoenzyme inhibitor |
url |
https://www.mdpi.com/1420-3049/25/3/701 |
work_keys_str_mv |
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