Synthesis, structural characterization, biological activity and molecular docking study of 4,7-dihydroxycoumarin modified by aminophenol derivatives
In the present manuscript, three different 4,7-dihydroxycoumarin derivatives were prepared and structurally characterized by crystallographic and spectroscopic techniques in combination with the B3LYP-D3BJ theoretical method. Cytotoxic and antimicrobial activities of investigated compounds were scre...
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| Format: | Article |
| Language: | English |
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Académie des sciences
2021-05-01
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| Series: | Comptes Rendus. Chimie |
| Subjects: | |
| Online Access: | https://comptes-rendus.academie-sciences.fr/chimie/articles/10.5802/crchim.68/ |
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| author | Milanović, Žiko B. Marković, Zoran S. Dimić, Dušan S. Klisurić, Olivera R. Radojević, Ivana D. Šeklić, Dragana S. Živanović, Marko N. Marković, Jasmina Dimitrić Radulović, Milanka Avdović, Edina H. |
| author_facet | Milanović, Žiko B. Marković, Zoran S. Dimić, Dušan S. Klisurić, Olivera R. Radojević, Ivana D. Šeklić, Dragana S. Živanović, Marko N. Marković, Jasmina Dimitrić Radulović, Milanka Avdović, Edina H. |
| author_sort | Milanović, Žiko B. |
| collection | DOAJ |
| description | In the present manuscript, three different 4,7-dihydroxycoumarin derivatives were prepared and structurally characterized by crystallographic and spectroscopic techniques in combination with the B3LYP-D3BJ theoretical method. Cytotoxic and antimicrobial activities of investigated compounds were screened against different cell lines and microorganisms. HCT-116 cells were most sensitive to the 3-(1-(2-hydroxyphenyl)amino) ethylidene)-2,4-dioxochroman-7-yl acetate derivative, while the best antimicrobial activity against Bacillus subtilis ATCC 6633 was shown by 3-(1-(2-hydroxyphenyl)amino)ethylidene)-2,4-dioxochroman-7-yl acetate. The molecular docking study for all compounds with important epidermal growth factor receptors (EGFR) was performed. The results indicate that the largest contribution to the binding energy is through conventional hydrogen bonds. |
| first_indexed | 2024-03-11T16:14:14Z |
| format | Article |
| id | doaj.art-741d6434ef3e427a835466d444c266ed |
| institution | Directory Open Access Journal |
| issn | 1878-1543 |
| language | English |
| last_indexed | 2024-03-11T16:14:14Z |
| publishDate | 2021-05-01 |
| publisher | Académie des sciences |
| record_format | Article |
| series | Comptes Rendus. Chimie |
| spelling | doaj.art-741d6434ef3e427a835466d444c266ed2023-10-24T14:22:55ZengAcadémie des sciencesComptes Rendus. Chimie1878-15432021-05-0124221523210.5802/crchim.6810.5802/crchim.68Synthesis, structural characterization, biological activity and molecular docking study of 4,7-dihydroxycoumarin modified by aminophenol derivativesMilanović, Žiko B.0Marković, Zoran S.1Dimić, Dušan S.2Klisurić, Olivera R.3Radojević, Ivana D.4Šeklić, Dragana S.5Živanović, Marko N.6Marković, Jasmina Dimitrić7Radulović, Milanka8Avdović, Edina H.9University of Kragujevac, Faculty of Science, Department of Chemistry, Radoja Domanovića 12, 34000 Kragujevac, SerbiaUniversity of Kragujevac, Institute of Information Technologies, Department of Science, Jovana Cvijića bb, 34000 Kragujevac, SerbiaFaculty of Physical Chemistry, University of Belgrade, 12-16 Studentski trg, 11000 Belgrade, SerbiaUniversity of Novi Sad, Faculty of Sciences, Department of Physics, Trg Dositeja Obradovića 4, 21 000 Novi Sad, SerbiaUniversity of Kragujevac, Faculty of Science, Department of Biology and Ecology, Radoja Domanovića 12, 34000 Kragujevac, SerbiaUniversity of Kragujevac, Institute of Information Technologies, Department of Science, Jovana Cvijića bb, 34000 Kragujevac, SerbiaUniversity of Kragujevac, Institute of Information Technologies, Department of Science, Jovana Cvijića bb, 34000 Kragujevac, SerbiaFaculty of Physical Chemistry, University of Belgrade, 12-16 Studentski trg, 11000 Belgrade, SerbiaState University of Novi Pazar, Department of Chemical-Technological Sciences, Vuka Karadžića bb, 36300, Novi Pazar, Republic of SerbiaUniversity of Kragujevac, Institute of Information Technologies, Department of Science, Jovana Cvijića bb, 34000 Kragujevac, SerbiaIn the present manuscript, three different 4,7-dihydroxycoumarin derivatives were prepared and structurally characterized by crystallographic and spectroscopic techniques in combination with the B3LYP-D3BJ theoretical method. Cytotoxic and antimicrobial activities of investigated compounds were screened against different cell lines and microorganisms. HCT-116 cells were most sensitive to the 3-(1-(2-hydroxyphenyl)amino) ethylidene)-2,4-dioxochroman-7-yl acetate derivative, while the best antimicrobial activity against Bacillus subtilis ATCC 6633 was shown by 3-(1-(2-hydroxyphenyl)amino)ethylidene)-2,4-dioxochroman-7-yl acetate. The molecular docking study for all compounds with important epidermal growth factor receptors (EGFR) was performed. The results indicate that the largest contribution to the binding energy is through conventional hydrogen bonds.https://comptes-rendus.academie-sciences.fr/chimie/articles/10.5802/crchim.68/Coumarin-derived ligands47-dihydroxycoumarinBiological activityDFT calculationsMolecular docking |
| spellingShingle | Milanović, Žiko B. Marković, Zoran S. Dimić, Dušan S. Klisurić, Olivera R. Radojević, Ivana D. Šeklić, Dragana S. Živanović, Marko N. Marković, Jasmina Dimitrić Radulović, Milanka Avdović, Edina H. Synthesis, structural characterization, biological activity and molecular docking study of 4,7-dihydroxycoumarin modified by aminophenol derivatives Comptes Rendus. Chimie Coumarin-derived ligands 4 7-dihydroxycoumarin Biological activity DFT calculations Molecular docking |
| title | Synthesis, structural characterization, biological activity and molecular docking study of 4,7-dihydroxycoumarin modified by aminophenol derivatives |
| title_full | Synthesis, structural characterization, biological activity and molecular docking study of 4,7-dihydroxycoumarin modified by aminophenol derivatives |
| title_fullStr | Synthesis, structural characterization, biological activity and molecular docking study of 4,7-dihydroxycoumarin modified by aminophenol derivatives |
| title_full_unstemmed | Synthesis, structural characterization, biological activity and molecular docking study of 4,7-dihydroxycoumarin modified by aminophenol derivatives |
| title_short | Synthesis, structural characterization, biological activity and molecular docking study of 4,7-dihydroxycoumarin modified by aminophenol derivatives |
| title_sort | synthesis structural characterization biological activity and molecular docking study of 4 7 dihydroxycoumarin modified by aminophenol derivatives |
| topic | Coumarin-derived ligands 4 7-dihydroxycoumarin Biological activity DFT calculations Molecular docking |
| url | https://comptes-rendus.academie-sciences.fr/chimie/articles/10.5802/crchim.68/ |
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