Computational studies of a series of 2-substituted phenyl-2-oxo-, 2-hydroxyl- and 2-acylloxyethylsulfonamides as potent anti-fungal agents
Botrytis Cinerea is a plant pathogen that affect a large number of plant species like tomatoes, Lettuce, Grapes, and Strawberries among others. Sulfonamides are widely used in pharmaceutical industries as anti-cancer, anti-inflammatory and anti-viral agents. To complement our previous QSAR study, a...
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Formato: | Online Artículo Texto |
Lenguaje: | English |
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Elsevier
2020
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Acceso en línea: | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC7160569/ https://www.ncbi.nlm.nih.gov/pubmed/32322718 http://dx.doi.org/10.1016/j.heliyon.2020.e03724 |
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author | Isyaku, Yusuf Uzairu, Adamu Uba, Sani |
author_facet | Isyaku, Yusuf Uzairu, Adamu Uba, Sani |
author_sort | Isyaku, Yusuf |
collection | PubMed |
description | Botrytis Cinerea is a plant pathogen that affect a large number of plant species like tomatoes, Lettuce, Grapes, and Strawberries among others. Sulfonamides are widely used in pharmaceutical industries as anti-cancer, anti-inflammatory and anti-viral agents. To complement our previous QSAR study, a ligand-based design and ADME/T study were carried out on these sulfonamides compounds for their fungicidal activity toward “Botrytis Cinerea”. With the help of AutoDock Vina version 4.0 in Pyrex software, the docking analysis was performed after optimization of the compounds at DFT/B3LYP/6-31G∗ quantum mechanical method using Spartan 14 softwar. Using the model generated in the previous QSAR work, the descriptors of the chosen model were considered in modifying the most promising compound ‘9’ in which twelve (12) derivatives were designed and found to have better activity than the template (compound 9). With compound 9j having the highest activity that turns out to be about 14 and 15 times more potent than the commercial fungicides “procymidone and chlorothalonil”. Furthermore, ADME/T properties of the designed compounds were calculated using the SwissADME online tool in which all the compounds were found to have good pharmacokinetic profile. Moreover, a molecular docking study on selected compounds of the dataset (compound 8, 13, 14, 19, 20, 21, 22 and 29) revealed that compound ‘20’ turned out to have the highest docking score of -8.5 kJ/mol. This compound has a strong affinity with the macromolecular target point (PDB ID: 3wh1) producing H-bond and hydrophobic interaction at the target point of amino acid residue. The molecular docking analysis gave an insight on the structure-based design of the new compounds with better activity against B. cinerea. |
format | Online Article Text |
id | pubmed-7160569 |
institution | National Center for Biotechnology Information |
language | English |
publishDate | 2020 |
publisher | Elsevier |
record_format | MEDLINE/PubMed |
spelling | pubmed-71605692020-04-22 Computational studies of a series of 2-substituted phenyl-2-oxo-, 2-hydroxyl- and 2-acylloxyethylsulfonamides as potent anti-fungal agents Isyaku, Yusuf Uzairu, Adamu Uba, Sani Heliyon Article Botrytis Cinerea is a plant pathogen that affect a large number of plant species like tomatoes, Lettuce, Grapes, and Strawberries among others. Sulfonamides are widely used in pharmaceutical industries as anti-cancer, anti-inflammatory and anti-viral agents. To complement our previous QSAR study, a ligand-based design and ADME/T study were carried out on these sulfonamides compounds for their fungicidal activity toward “Botrytis Cinerea”. With the help of AutoDock Vina version 4.0 in Pyrex software, the docking analysis was performed after optimization of the compounds at DFT/B3LYP/6-31G∗ quantum mechanical method using Spartan 14 softwar. Using the model generated in the previous QSAR work, the descriptors of the chosen model were considered in modifying the most promising compound ‘9’ in which twelve (12) derivatives were designed and found to have better activity than the template (compound 9). With compound 9j having the highest activity that turns out to be about 14 and 15 times more potent than the commercial fungicides “procymidone and chlorothalonil”. Furthermore, ADME/T properties of the designed compounds were calculated using the SwissADME online tool in which all the compounds were found to have good pharmacokinetic profile. Moreover, a molecular docking study on selected compounds of the dataset (compound 8, 13, 14, 19, 20, 21, 22 and 29) revealed that compound ‘20’ turned out to have the highest docking score of -8.5 kJ/mol. This compound has a strong affinity with the macromolecular target point (PDB ID: 3wh1) producing H-bond and hydrophobic interaction at the target point of amino acid residue. The molecular docking analysis gave an insight on the structure-based design of the new compounds with better activity against B. cinerea. Elsevier 2020-04-14 /pmc/articles/PMC7160569/ /pubmed/32322718 http://dx.doi.org/10.1016/j.heliyon.2020.e03724 Text en © 2020 The Author(s) http://creativecommons.org/licenses/by/4.0/ This is an open access article under the CC BY license (http://creativecommons.org/licenses/by/4.0/). |
spellingShingle | Article Isyaku, Yusuf Uzairu, Adamu Uba, Sani Computational studies of a series of 2-substituted phenyl-2-oxo-, 2-hydroxyl- and 2-acylloxyethylsulfonamides as potent anti-fungal agents |
title | Computational studies of a series of 2-substituted phenyl-2-oxo-, 2-hydroxyl- and 2-acylloxyethylsulfonamides as potent anti-fungal agents |
title_full | Computational studies of a series of 2-substituted phenyl-2-oxo-, 2-hydroxyl- and 2-acylloxyethylsulfonamides as potent anti-fungal agents |
title_fullStr | Computational studies of a series of 2-substituted phenyl-2-oxo-, 2-hydroxyl- and 2-acylloxyethylsulfonamides as potent anti-fungal agents |
title_full_unstemmed | Computational studies of a series of 2-substituted phenyl-2-oxo-, 2-hydroxyl- and 2-acylloxyethylsulfonamides as potent anti-fungal agents |
title_short | Computational studies of a series of 2-substituted phenyl-2-oxo-, 2-hydroxyl- and 2-acylloxyethylsulfonamides as potent anti-fungal agents |
title_sort | computational studies of a series of 2-substituted phenyl-2-oxo-, 2-hydroxyl- and 2-acylloxyethylsulfonamides as potent anti-fungal agents |
topic | Article |
url | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC7160569/ https://www.ncbi.nlm.nih.gov/pubmed/32322718 http://dx.doi.org/10.1016/j.heliyon.2020.e03724 |
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