New solid phase methodology for the synthesis of biscoumarin derivatives: experimental and in silico approaches
Abstract The simple and greener one-pot approach for the synthesis of biscoumarin derivatives using catalytic amounts of nano-MoO3 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 th...
| Main Authors: | , , , , |
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| Format: | Article |
| Language: | English |
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BMC
2022-07-01
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| Series: | BMC Chemistry |
| Subjects: | |
| Online Access: | https://doi.org/10.1186/s13065-022-00844-8 |
| _version_ | 1811293794482520064 |
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| author | Elham Zarenezhad Mohammad Nazari Montazer Masoumeh Tabatabaee Cambyz Irajie Aida Iraji |
| author_facet | Elham Zarenezhad Mohammad Nazari Montazer Masoumeh Tabatabaee Cambyz Irajie Aida Iraji |
| author_sort | Elham Zarenezhad |
| collection | DOAJ |
| description | Abstract The simple and greener one-pot approach for the synthesis of biscoumarin derivatives using catalytic amounts of nano-MoO3 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. |
| first_indexed | 2024-04-13T05:06:47Z |
| format | Article |
| id | doaj.art-e4103d58cf2b4da7b8fa4657eec4c062 |
| institution | Directory Open Access Journal |
| issn | 2661-801X |
| language | English |
| last_indexed | 2024-04-13T05:06:47Z |
| publishDate | 2022-07-01 |
| publisher | BMC |
| record_format | Article |
| series | BMC Chemistry |
| spelling | doaj.art-e4103d58cf2b4da7b8fa4657eec4c0622022-12-22T03:01:09ZengBMCBMC Chemistry2661-801X2022-07-0116111610.1186/s13065-022-00844-8New solid phase methodology for the synthesis of biscoumarin derivatives: experimental and in silico approachesElham Zarenezhad0Mohammad Nazari Montazer1Masoumeh Tabatabaee2Cambyz Irajie3Aida Iraji4Noncommunicable Diseases Research Center, Fasa University of Medical SciencesDepartment of Medicinal Chemistry, Faculty of Pharmacy, Tehran University of Medical SciencesDepartment of Chemistry, Yazd Branch, Islamic Azad UniversityDepartment of Medical Biotechnology, School of Advanced Medical Sciences and Technologies, Shiraz University of Medical SciencesStem Cells Technology Research Center, Shiraz University of Medical SciencesAbstract The simple and greener one-pot approach for the synthesis of biscoumarin derivatives using catalytic amounts of nano-MoO3 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.https://doi.org/10.1186/s13065-022-00844-8Molecular dynamics simulationsMM-GBSABiscoumarinMoO3-nanoparticle |
| spellingShingle | Elham Zarenezhad Mohammad Nazari Montazer Masoumeh Tabatabaee Cambyz Irajie Aida Iraji New solid phase methodology for the synthesis of biscoumarin derivatives: experimental and in silico approaches BMC Chemistry Molecular dynamics simulations MM-GBSA Biscoumarin MoO3-nanoparticle |
| 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 | Molecular dynamics simulations MM-GBSA Biscoumarin MoO3-nanoparticle |
| url | https://doi.org/10.1186/s13065-022-00844-8 |
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