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An efficient and targeted synthetic approach towards new highly substituted 6-amino-pyrazolo[1,5-a]pyrimidines with α-glucosidase inhibitory activity

In an attempt to find novel α-glucosidase inhibitors, an efficient, straightforward reaction to synthesize a library of fully substituted 6-amino-pyrazolo[1,5-a]pyrimidines 3 has been investigated. Heating a mixture of α-azidochalcones 1 and 3-aminopyrazoles 2 under the mild condition afforded desir...

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Autores principales: Peytam, Fariba, Adib, Mehdi, Shourgeshty, Reihaneh, Firoozpour, Loghman, Rahmanian-Jazi, Mahmoud, Jahani, Mehdi, Moghimi, Setareh, Divsalar, Kouros, Faramarzi, Mohammad Ali, Mojtabavi, Somayeh, Safari, Fatemeh, Mahdavi, Mohammad, Foroumadi, Alireza
Formato: Online Artículo Texto
Lenguaje:English
Publicado: Nature Publishing Group UK 2020
Materias:
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC7018746/
https://www.ncbi.nlm.nih.gov/pubmed/32054916
http://dx.doi.org/10.1038/s41598-020-59079-z
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author Peytam, Fariba
Adib, Mehdi
Shourgeshty, Reihaneh
Firoozpour, Loghman
Rahmanian-Jazi, Mahmoud
Jahani, Mehdi
Moghimi, Setareh
Divsalar, Kouros
Faramarzi, Mohammad Ali
Mojtabavi, Somayeh
Safari, Fatemeh
Mahdavi, Mohammad
Foroumadi, Alireza
author_facet Peytam, Fariba
Adib, Mehdi
Shourgeshty, Reihaneh
Firoozpour, Loghman
Rahmanian-Jazi, Mahmoud
Jahani, Mehdi
Moghimi, Setareh
Divsalar, Kouros
Faramarzi, Mohammad Ali
Mojtabavi, Somayeh
Safari, Fatemeh
Mahdavi, Mohammad
Foroumadi, Alireza
author_sort Peytam, Fariba
collection PubMed
description In an attempt to find novel α-glucosidase inhibitors, an efficient, straightforward reaction to synthesize a library of fully substituted 6-amino-pyrazolo[1,5-a]pyrimidines 3 has been investigated. Heating a mixture of α-azidochalcones 1 and 3-aminopyrazoles 2 under the mild condition afforded desired compounds with a large substrate scope in good to excellent yields. All obtained products were evaluated as α-glucosidase inhibitors and exhibited excellent potency with IC(50) values ranging from 15.2 ± 0.4 µM to 201.3 ± 4.2 µM. Among them, compound 3d was around 50-fold more potent than acarbose (IC(50) = 750.0 ± 1.5 µM) as standard inhibitor. Regarding product structures, kinetic study and molecular docking were carried out for two of the most potent ones.
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spelling pubmed-70187462020-02-21 An efficient and targeted synthetic approach towards new highly substituted 6-amino-pyrazolo[1,5-a]pyrimidines with α-glucosidase inhibitory activity Peytam, Fariba Adib, Mehdi Shourgeshty, Reihaneh Firoozpour, Loghman Rahmanian-Jazi, Mahmoud Jahani, Mehdi Moghimi, Setareh Divsalar, Kouros Faramarzi, Mohammad Ali Mojtabavi, Somayeh Safari, Fatemeh Mahdavi, Mohammad Foroumadi, Alireza Sci Rep Article In an attempt to find novel α-glucosidase inhibitors, an efficient, straightforward reaction to synthesize a library of fully substituted 6-amino-pyrazolo[1,5-a]pyrimidines 3 has been investigated. Heating a mixture of α-azidochalcones 1 and 3-aminopyrazoles 2 under the mild condition afforded desired compounds with a large substrate scope in good to excellent yields. All obtained products were evaluated as α-glucosidase inhibitors and exhibited excellent potency with IC(50) values ranging from 15.2 ± 0.4 µM to 201.3 ± 4.2 µM. Among them, compound 3d was around 50-fold more potent than acarbose (IC(50) = 750.0 ± 1.5 µM) as standard inhibitor. Regarding product structures, kinetic study and molecular docking were carried out for two of the most potent ones. Nature Publishing Group UK 2020-02-13 /pmc/articles/PMC7018746/ /pubmed/32054916 http://dx.doi.org/10.1038/s41598-020-59079-z Text en © The Author(s) 2020 Open Access This article is licensed under a Creative Commons Attribution 4.0 International License, which permits use, sharing, adaptation, distribution and reproduction in any medium or format, as long as you give appropriate credit to the original author(s) and the source, provide a link to the Creative Commons license, and indicate if changes were made. The images or other third party material in this article are included in the article’s Creative Commons license, unless indicated otherwise in a credit line to the material. If material is not included in the article’s Creative Commons license and your intended use is not permitted by statutory regulation or exceeds the permitted use, you will need to obtain permission directly from the copyright holder. To view a copy of this license, visit http://creativecommons.org/licenses/by/4.0/.
spellingShingle Article
Peytam, Fariba
Adib, Mehdi
Shourgeshty, Reihaneh
Firoozpour, Loghman
Rahmanian-Jazi, Mahmoud
Jahani, Mehdi
Moghimi, Setareh
Divsalar, Kouros
Faramarzi, Mohammad Ali
Mojtabavi, Somayeh
Safari, Fatemeh
Mahdavi, Mohammad
Foroumadi, Alireza
An efficient and targeted synthetic approach towards new highly substituted 6-amino-pyrazolo[1,5-a]pyrimidines with α-glucosidase inhibitory activity
title An efficient and targeted synthetic approach towards new highly substituted 6-amino-pyrazolo[1,5-a]pyrimidines with α-glucosidase inhibitory activity
title_full An efficient and targeted synthetic approach towards new highly substituted 6-amino-pyrazolo[1,5-a]pyrimidines with α-glucosidase inhibitory activity
title_fullStr An efficient and targeted synthetic approach towards new highly substituted 6-amino-pyrazolo[1,5-a]pyrimidines with α-glucosidase inhibitory activity
title_full_unstemmed An efficient and targeted synthetic approach towards new highly substituted 6-amino-pyrazolo[1,5-a]pyrimidines with α-glucosidase inhibitory activity
title_short An efficient and targeted synthetic approach towards new highly substituted 6-amino-pyrazolo[1,5-a]pyrimidines with α-glucosidase inhibitory activity
title_sort efficient and targeted synthetic approach towards new highly substituted 6-amino-pyrazolo[1,5-a]pyrimidines with α-glucosidase inhibitory activity
topic Article
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC7018746/
https://www.ncbi.nlm.nih.gov/pubmed/32054916
http://dx.doi.org/10.1038/s41598-020-59079-z
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