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One-pot multi-component synthesis of novel chromeno[4,3-b]pyrrol-3-yl derivatives as alpha-glucosidase inhibitors
A green and efficient one-pot multi-component protocol was developed for the synthesis of some novel dihydrochromeno[4,3-b]pyrrol-3-yl derivatives through the reaction of arylglyoxals, malono derivatives, and different 4-amino coumarins in ethanol at reflux condition. In this method, all products we...
Autores principales: | , , , , , , |
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Formato: | Online Artículo Texto |
Lenguaje: | English |
Publicado: |
Springer International Publishing
2021
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Materias: | |
Acceso en línea: | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC8544188/ https://www.ncbi.nlm.nih.gov/pubmed/34697701 http://dx.doi.org/10.1007/s11030-021-10337-w |
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author | Karami, Malihe Hasaninejad, Alireza Mahdavi, Hossein Iraji, Aida Mojtabavi, Somayeh Faramarzi, Mohammad Ali Mahdavi, Mohammad |
author_facet | Karami, Malihe Hasaninejad, Alireza Mahdavi, Hossein Iraji, Aida Mojtabavi, Somayeh Faramarzi, Mohammad Ali Mahdavi, Mohammad |
author_sort | Karami, Malihe |
collection | PubMed |
description | A green and efficient one-pot multi-component protocol was developed for the synthesis of some novel dihydrochromeno[4,3-b]pyrrol-3-yl derivatives through the reaction of arylglyoxals, malono derivatives, and different 4-amino coumarins in ethanol at reflux condition. In this method, all products were obtained in good to excellent yield. Next, all synthesized derivatives were evaluated for their α-glucosidase inhibitory activity. Most of the compounds displayed potent inhibitory activities with IC(50) values in the range of 48.65 ± 0.01–733.83 ± 0.10 μM compared to the standard inhibitor acarbose (IC(50) = 750.90 ± 0.14 μM). The kinetic study of compound 5e as the most potent derivative (IC(50) = 48.65 ± 0.01 μM) showed a competitive mechanism with a K(i) value of 42.6 µM. Moreover, docking studies revealed that dihydrochromeno[4,3-b]pyrrol-3-yl effectively interacted with important residues in the active site of α-glucosidase. SUPPLEMENTARY INFORMATION: The online version contains supplementary material available at 10.1007/s11030-021-10337-w. |
format | Online Article Text |
id | pubmed-8544188 |
institution | National Center for Biotechnology Information |
language | English |
publishDate | 2021 |
publisher | Springer International Publishing |
record_format | MEDLINE/PubMed |
spelling | pubmed-85441882021-10-26 One-pot multi-component synthesis of novel chromeno[4,3-b]pyrrol-3-yl derivatives as alpha-glucosidase inhibitors Karami, Malihe Hasaninejad, Alireza Mahdavi, Hossein Iraji, Aida Mojtabavi, Somayeh Faramarzi, Mohammad Ali Mahdavi, Mohammad Mol Divers Original Article A green and efficient one-pot multi-component protocol was developed for the synthesis of some novel dihydrochromeno[4,3-b]pyrrol-3-yl derivatives through the reaction of arylglyoxals, malono derivatives, and different 4-amino coumarins in ethanol at reflux condition. In this method, all products were obtained in good to excellent yield. Next, all synthesized derivatives were evaluated for their α-glucosidase inhibitory activity. Most of the compounds displayed potent inhibitory activities with IC(50) values in the range of 48.65 ± 0.01–733.83 ± 0.10 μM compared to the standard inhibitor acarbose (IC(50) = 750.90 ± 0.14 μM). The kinetic study of compound 5e as the most potent derivative (IC(50) = 48.65 ± 0.01 μM) showed a competitive mechanism with a K(i) value of 42.6 µM. Moreover, docking studies revealed that dihydrochromeno[4,3-b]pyrrol-3-yl effectively interacted with important residues in the active site of α-glucosidase. SUPPLEMENTARY INFORMATION: The online version contains supplementary material available at 10.1007/s11030-021-10337-w. Springer International Publishing 2021-10-25 2022 /pmc/articles/PMC8544188/ /pubmed/34697701 http://dx.doi.org/10.1007/s11030-021-10337-w Text en © The Author(s), under exclusive licence to Springer Nature Switzerland AG 2021 This article is made available via the PMC Open Access Subset for unrestricted research re-use and secondary analysis in any form or by any means with acknowledgement of the original source. These permissions are granted for the duration of the World Health Organization (WHO) declaration of COVID-19 as a global pandemic. |
spellingShingle | Original Article Karami, Malihe Hasaninejad, Alireza Mahdavi, Hossein Iraji, Aida Mojtabavi, Somayeh Faramarzi, Mohammad Ali Mahdavi, Mohammad One-pot multi-component synthesis of novel chromeno[4,3-b]pyrrol-3-yl derivatives as alpha-glucosidase inhibitors |
title | One-pot multi-component synthesis of novel chromeno[4,3-b]pyrrol-3-yl derivatives as alpha-glucosidase inhibitors |
title_full | One-pot multi-component synthesis of novel chromeno[4,3-b]pyrrol-3-yl derivatives as alpha-glucosidase inhibitors |
title_fullStr | One-pot multi-component synthesis of novel chromeno[4,3-b]pyrrol-3-yl derivatives as alpha-glucosidase inhibitors |
title_full_unstemmed | One-pot multi-component synthesis of novel chromeno[4,3-b]pyrrol-3-yl derivatives as alpha-glucosidase inhibitors |
title_short | One-pot multi-component synthesis of novel chromeno[4,3-b]pyrrol-3-yl derivatives as alpha-glucosidase inhibitors |
title_sort | one-pot multi-component synthesis of novel chromeno[4,3-b]pyrrol-3-yl derivatives as alpha-glucosidase inhibitors |
topic | Original Article |
url | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC8544188/ https://www.ncbi.nlm.nih.gov/pubmed/34697701 http://dx.doi.org/10.1007/s11030-021-10337-w |
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