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Design and Synthesis of New Benzimidazole and Pyrimidine Derivatives as α-glucosidase Inhibitor

In an endeavor to find a novel series of antihyperglycemic agents, new benzimidazole and pyrimidine derivatives were successfully synthesized efficiently in high yield with high purity, starting from amino acids in the presence of phosphorus oxychloride (POCl(3)). The synthesized compounds were iden...

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Autores principales: Mobinikhaledi, Akbar, Asghari, Behvar, Jabbarpour, Mahsa
Formato: Online Artículo Texto
Lenguaje:English
Publicado: Shaheed Beheshti University of Medical Sciences 2015
Materias:
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC4518100/
https://www.ncbi.nlm.nih.gov/pubmed/26330860
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author Mobinikhaledi, Akbar
Asghari, Behvar
Jabbarpour, Mahsa
author_facet Mobinikhaledi, Akbar
Asghari, Behvar
Jabbarpour, Mahsa
author_sort Mobinikhaledi, Akbar
collection PubMed
description In an endeavor to find a novel series of antihyperglycemic agents, new benzimidazole and pyrimidine derivatives were successfully synthesized efficiently in high yield with high purity, starting from amino acids in the presence of phosphorus oxychloride (POCl(3)). The synthesized compounds were identified by (1)H-NMR, (13)C-NMR, FT-IR spectroscopic techniques and elemental analysis. All products were assayed for their inhibitory effects on yeast and rat intestinal α-glucosidases. The results revealed that compounds with aromatic amino acids moiety showed significant inhibition activity on the tested enzymes. Among the benzimidazole derivatives 4c and 4d exhibited the best activity against both of the tested enzymes. Also, among the pyrimidine derivatives 5c and 5d possessed significant inhibition action on the enzymes. The IC(50) values for the most potent benzimidazole yeast and intestinal α-glucosidases inhibitor (4d) were found to be 9.1 and 36.7 µM, respectively. The IC(50) values for the inhibition of yeast and intestinal α-glucosidases by the most active pyrimidine compound (5d) were calculated to be 8.3 and 21.8 µM, respectively. Overall, this study proved that benzimidazole and pyrimidine derivatives with aromatic amino acids moieties can represent novel promising α-glucosidase inhibitors.
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spelling pubmed-45181002015-09-01 Design and Synthesis of New Benzimidazole and Pyrimidine Derivatives as α-glucosidase Inhibitor Mobinikhaledi, Akbar Asghari, Behvar Jabbarpour, Mahsa Iran J Pharm Res Original Article In an endeavor to find a novel series of antihyperglycemic agents, new benzimidazole and pyrimidine derivatives were successfully synthesized efficiently in high yield with high purity, starting from amino acids in the presence of phosphorus oxychloride (POCl(3)). The synthesized compounds were identified by (1)H-NMR, (13)C-NMR, FT-IR spectroscopic techniques and elemental analysis. All products were assayed for their inhibitory effects on yeast and rat intestinal α-glucosidases. The results revealed that compounds with aromatic amino acids moiety showed significant inhibition activity on the tested enzymes. Among the benzimidazole derivatives 4c and 4d exhibited the best activity against both of the tested enzymes. Also, among the pyrimidine derivatives 5c and 5d possessed significant inhibition action on the enzymes. The IC(50) values for the most potent benzimidazole yeast and intestinal α-glucosidases inhibitor (4d) were found to be 9.1 and 36.7 µM, respectively. The IC(50) values for the inhibition of yeast and intestinal α-glucosidases by the most active pyrimidine compound (5d) were calculated to be 8.3 and 21.8 µM, respectively. Overall, this study proved that benzimidazole and pyrimidine derivatives with aromatic amino acids moieties can represent novel promising α-glucosidase inhibitors. Shaheed Beheshti University of Medical Sciences 2015 /pmc/articles/PMC4518100/ /pubmed/26330860 Text en © 2015 by School of Pharmacy, Shaheed Beheshti University of Medical Sciences and Health Services This is an Open Access article distributed under the terms of the Creative Commons Attribution License, (http://creativecommons.org/licenses/by/3.0/) which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited.
spellingShingle Original Article
Mobinikhaledi, Akbar
Asghari, Behvar
Jabbarpour, Mahsa
Design and Synthesis of New Benzimidazole and Pyrimidine Derivatives as α-glucosidase Inhibitor
title Design and Synthesis of New Benzimidazole and Pyrimidine Derivatives as α-glucosidase Inhibitor
title_full Design and Synthesis of New Benzimidazole and Pyrimidine Derivatives as α-glucosidase Inhibitor
title_fullStr Design and Synthesis of New Benzimidazole and Pyrimidine Derivatives as α-glucosidase Inhibitor
title_full_unstemmed Design and Synthesis of New Benzimidazole and Pyrimidine Derivatives as α-glucosidase Inhibitor
title_short Design and Synthesis of New Benzimidazole and Pyrimidine Derivatives as α-glucosidase Inhibitor
title_sort design and synthesis of new benzimidazole and pyrimidine derivatives as α-glucosidase inhibitor
topic Original Article
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC4518100/
https://www.ncbi.nlm.nih.gov/pubmed/26330860
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