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New solid phase methodology for the synthesis of biscoumarin derivatives: experimental and in silico approaches
The simple and greener one-pot approach for the synthesis of biscoumarin derivatives using catalytic amounts of nano-MoO(3) catalyst under mortar-pestle grinding was described. The use of non-toxic and mild catalyst, cost-effectiveness, ordinary grinding, and good to the excellent yield of the final...
Autores principales: | , , , , |
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Formato: | Online Artículo Texto |
Lenguaje: | English |
Publicado: |
Springer International Publishing
2022
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Materias: | |
Acceso en línea: | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC9275028/ https://www.ncbi.nlm.nih.gov/pubmed/35820918 http://dx.doi.org/10.1186/s13065-022-00844-8 |
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author | Zarenezhad, Elham Montazer, Mohammad Nazari Tabatabaee, Masoumeh Irajie, Cambyz Iraji, Aida |
author_facet | Zarenezhad, Elham Montazer, Mohammad Nazari Tabatabaee, Masoumeh Irajie, Cambyz Iraji, Aida |
author_sort | Zarenezhad, Elham |
collection | PubMed |
description | The simple and greener one-pot approach for the synthesis of biscoumarin derivatives using catalytic amounts of nano-MoO(3) catalyst under mortar-pestle grinding was described. The use of non-toxic and mild catalyst, cost-effectiveness, ordinary grinding, and good to the excellent yield of the final product makes this procedure a more attractive pathway for the synthesis of biologically remarkable pharmacophores. Accordingly, biscoumarin derivatives were successfully extended in the developed protocols. Next, a computational investigation was performed to identify the potential biological targets of this set of compounds. In this case, first, a similarity search on different virtual libraries was performed to find an ideal biological target for these derivatives. Results showed that the synthesized derivatives can be α-glucosidase inhibitors. In another step, molecular docking studies were carried out against human lysosomal acid-alpha-glucosidase (PDB ID: 5NN8) to determine the detailed binding modes and critical interactions with the proposed target. In silico assessments showed the gold score value in the range of 17.56 to 29.49. Additionally, molecular dynamic simulations and the MM-GBSA method of the most active derivative against α-glucosidase were conducted to study the behavior of selected compounds in the biological system. Ligand 1 stabilized after around 30 ns and participated in various interactions with Trp481, Asp518, Asp616, His674, Phe649, and Leu677 residues. |
format | Online Article Text |
id | pubmed-9275028 |
institution | National Center for Biotechnology Information |
language | English |
publishDate | 2022 |
publisher | Springer International Publishing |
record_format | MEDLINE/PubMed |
spelling | pubmed-92750282022-07-13 New solid phase methodology for the synthesis of biscoumarin derivatives: experimental and in silico approaches Zarenezhad, Elham Montazer, Mohammad Nazari Tabatabaee, Masoumeh Irajie, Cambyz Iraji, Aida BMC Chem Research The simple and greener one-pot approach for the synthesis of biscoumarin derivatives using catalytic amounts of nano-MoO(3) catalyst under mortar-pestle grinding was described. The use of non-toxic and mild catalyst, cost-effectiveness, ordinary grinding, and good to the excellent yield of the final product makes this procedure a more attractive pathway for the synthesis of biologically remarkable pharmacophores. Accordingly, biscoumarin derivatives were successfully extended in the developed protocols. Next, a computational investigation was performed to identify the potential biological targets of this set of compounds. In this case, first, a similarity search on different virtual libraries was performed to find an ideal biological target for these derivatives. Results showed that the synthesized derivatives can be α-glucosidase inhibitors. In another step, molecular docking studies were carried out against human lysosomal acid-alpha-glucosidase (PDB ID: 5NN8) to determine the detailed binding modes and critical interactions with the proposed target. In silico assessments showed the gold score value in the range of 17.56 to 29.49. Additionally, molecular dynamic simulations and the MM-GBSA method of the most active derivative against α-glucosidase were conducted to study the behavior of selected compounds in the biological system. Ligand 1 stabilized after around 30 ns and participated in various interactions with Trp481, Asp518, Asp616, His674, Phe649, and Leu677 residues. Springer International Publishing 2022-07-11 /pmc/articles/PMC9275028/ /pubmed/35820918 http://dx.doi.org/10.1186/s13065-022-00844-8 Text en © The Author(s) 2022 https://creativecommons.org/licenses/by/4.0/Open AccessThis 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 licence, and indicate if changes were made. The images or other third party material in this article are included in the article's Creative Commons licence, unless indicated otherwise in a credit line to the material. If material is not included in the article's Creative Commons licence 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 licence, visit http://creativecommons.org/licenses/by/4.0/ (https://creativecommons.org/licenses/by/4.0/) . The Creative Commons Public Domain Dedication waiver (http://creativecommons.org/publicdomain/zero/1.0/ (https://creativecommons.org/publicdomain/zero/1.0/) ) applies to the data made available in this article, unless otherwise stated in a credit line to the data. |
spellingShingle | Research Zarenezhad, Elham Montazer, Mohammad Nazari Tabatabaee, Masoumeh Irajie, Cambyz Iraji, Aida New solid phase methodology for the synthesis of biscoumarin derivatives: experimental and in silico approaches |
title | New solid phase methodology for the synthesis of biscoumarin derivatives: experimental and in silico approaches |
title_full | New solid phase methodology for the synthesis of biscoumarin derivatives: experimental and in silico approaches |
title_fullStr | New solid phase methodology for the synthesis of biscoumarin derivatives: experimental and in silico approaches |
title_full_unstemmed | New solid phase methodology for the synthesis of biscoumarin derivatives: experimental and in silico approaches |
title_short | New solid phase methodology for the synthesis of biscoumarin derivatives: experimental and in silico approaches |
title_sort | new solid phase methodology for the synthesis of biscoumarin derivatives: experimental and in silico approaches |
topic | Research |
url | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC9275028/ https://www.ncbi.nlm.nih.gov/pubmed/35820918 http://dx.doi.org/10.1186/s13065-022-00844-8 |
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