Synthesis, Molecular Docking, and Biological Evaluation of Novel Anthranilic Acid Hybrid and Its Diamides as Antispasmodics
The present article focuses on the synthesis and biological evaluation of a novel anthranilic acid hybrid and its diamides as antispasmodics. Methods: Due to the predicted in silico methods spasmolytic activity, we synthesized a hybrid molecule of anthranilic acid and 2-(3-chlorophenyl)ethylamine. T...
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| Format: | Article |
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MDPI AG
2023-09-01
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| Series: | International Journal of Molecular Sciences |
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| Online Access: | https://www.mdpi.com/1422-0067/24/18/13855 |
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| author | Miglena Milusheva Vera Gledacheva Iliyana Stefanova Mehran Feizi-Dehnayebi Rositsa Mihaylova Paraskev Nedialkov Emiliya Cherneva Yulian Tumbarski Slava Tsoneva Mina Todorova Stoyanka Nikolova |
| author_facet | Miglena Milusheva Vera Gledacheva Iliyana Stefanova Mehran Feizi-Dehnayebi Rositsa Mihaylova Paraskev Nedialkov Emiliya Cherneva Yulian Tumbarski Slava Tsoneva Mina Todorova Stoyanka Nikolova |
| author_sort | Miglena Milusheva |
| collection | DOAJ |
| description | The present article focuses on the synthesis and biological evaluation of a novel anthranilic acid hybrid and its diamides as antispasmodics. Methods: Due to the predicted in silico methods spasmolytic activity, we synthesized a hybrid molecule of anthranilic acid and 2-(3-chlorophenyl)ethylamine. The obtained hybrid was then applied in acylation with different acyl chlorides. Using in silico analysis, pharmacodynamic profiles of the compounds were predicted. A thorough biological evaluation of the compounds was conducted assessing their in vitro antimicrobial, cytotoxic, anti-inflammatory activity, and ex vivo spasmolytic activity. Density functional theory (DFT) calculation, including geometry optimization, molecular electrostatic potential (MEP) surface, and HOMO-LUMO analysis for the synthesized compounds was conducted using the B3LYP/6–311G(d,p) method to explore the electronic behavior, reactive regions, and stability and chemical reactivity of the compounds. Furthermore, molecular docking simulation along with viscosity measurement indicated that the newly synthesized compounds interact with DNA via groove binding mode. The obtained results from all the experiments demonstrate that the hybrid molecule and its diamides inherit spasmolytic, antimicrobial, and anti-inflammatory capabilities, making them excellent candidates for future medications. |
| first_indexed | 2024-03-10T22:40:48Z |
| format | Article |
| id | doaj.art-f1d5457610e444589b1307788072a5d6 |
| institution | Directory Open Access Journal |
| issn | 1661-6596 1422-0067 |
| language | English |
| last_indexed | 2024-03-10T22:40:48Z |
| publishDate | 2023-09-01 |
| publisher | MDPI AG |
| record_format | Article |
| series | International Journal of Molecular Sciences |
| spelling | doaj.art-f1d5457610e444589b1307788072a5d62023-11-19T11:04:09ZengMDPI AGInternational Journal of Molecular Sciences1661-65961422-00672023-09-0124181385510.3390/ijms241813855Synthesis, Molecular Docking, and Biological Evaluation of Novel Anthranilic Acid Hybrid and Its Diamides as AntispasmodicsMiglena Milusheva0Vera Gledacheva1Iliyana Stefanova2Mehran Feizi-Dehnayebi3Rositsa Mihaylova4Paraskev Nedialkov5Emiliya Cherneva6Yulian Tumbarski7Slava Tsoneva8Mina Todorova9Stoyanka Nikolova10Department of Organic Chemistry, Faculty of Chemistry, University of Plovdiv, 4000 Plovdiv, BulgariaDepartment of Medical Physics and Biophysics, Faculty of Pharmacy, Medical University of Plovdiv, 4002 Plovdiv, BulgariaDepartment of Medical Physics and Biophysics, Faculty of Pharmacy, Medical University of Plovdiv, 4002 Plovdiv, BulgariaDepartment of Chemistry, Faculty of Science, University of Sistan and Baluchestan, Zahedan P.O. Box 98135-674, IranLaboratory of Experimental Chemotherapy, Department “Pharmacology, Pharmacotherapy and Toxicology”, Faculty of Pharmacy, Medical University, 1431 Sofia, BulgariaDepartment of Pharmacognosy, Faculty of Pharmacy, Medical University of Sofia, 1000 Sofia, BulgariaDepartment of Chemistry, Faculty of Pharmacy, Medical University of Sofia, 2 Dunav Str., 1000 Sofia, BulgariaDepartment of Microbiology, Technological Faculty, University of Food Technologies, 4002 Plovdiv, BulgariaDepartment of Analytical Chemistry and Computer Chemistry, University of Plovdiv, 4000 Plovdiv, BulgariaDepartment of Organic Chemistry, Faculty of Chemistry, University of Plovdiv, 4000 Plovdiv, BulgariaDepartment of Organic Chemistry, Faculty of Chemistry, University of Plovdiv, 4000 Plovdiv, BulgariaThe present article focuses on the synthesis and biological evaluation of a novel anthranilic acid hybrid and its diamides as antispasmodics. Methods: Due to the predicted in silico methods spasmolytic activity, we synthesized a hybrid molecule of anthranilic acid and 2-(3-chlorophenyl)ethylamine. The obtained hybrid was then applied in acylation with different acyl chlorides. Using in silico analysis, pharmacodynamic profiles of the compounds were predicted. A thorough biological evaluation of the compounds was conducted assessing their in vitro antimicrobial, cytotoxic, anti-inflammatory activity, and ex vivo spasmolytic activity. Density functional theory (DFT) calculation, including geometry optimization, molecular electrostatic potential (MEP) surface, and HOMO-LUMO analysis for the synthesized compounds was conducted using the B3LYP/6–311G(d,p) method to explore the electronic behavior, reactive regions, and stability and chemical reactivity of the compounds. Furthermore, molecular docking simulation along with viscosity measurement indicated that the newly synthesized compounds interact with DNA via groove binding mode. The obtained results from all the experiments demonstrate that the hybrid molecule and its diamides inherit spasmolytic, antimicrobial, and anti-inflammatory capabilities, making them excellent candidates for future medications.https://www.mdpi.com/1422-0067/24/18/13855anthranilic acidhybrid moleculesin silicoDFTantiproliferativeantimicrobial |
| spellingShingle | Miglena Milusheva Vera Gledacheva Iliyana Stefanova Mehran Feizi-Dehnayebi Rositsa Mihaylova Paraskev Nedialkov Emiliya Cherneva Yulian Tumbarski Slava Tsoneva Mina Todorova Stoyanka Nikolova Synthesis, Molecular Docking, and Biological Evaluation of Novel Anthranilic Acid Hybrid and Its Diamides as Antispasmodics International Journal of Molecular Sciences anthranilic acid hybrid molecules in silico DFT antiproliferative antimicrobial |
| title | Synthesis, Molecular Docking, and Biological Evaluation of Novel Anthranilic Acid Hybrid and Its Diamides as Antispasmodics |
| title_full | Synthesis, Molecular Docking, and Biological Evaluation of Novel Anthranilic Acid Hybrid and Its Diamides as Antispasmodics |
| title_fullStr | Synthesis, Molecular Docking, and Biological Evaluation of Novel Anthranilic Acid Hybrid and Its Diamides as Antispasmodics |
| title_full_unstemmed | Synthesis, Molecular Docking, and Biological Evaluation of Novel Anthranilic Acid Hybrid and Its Diamides as Antispasmodics |
| title_short | Synthesis, Molecular Docking, and Biological Evaluation of Novel Anthranilic Acid Hybrid and Its Diamides as Antispasmodics |
| title_sort | synthesis molecular docking and biological evaluation of novel anthranilic acid hybrid and its diamides as antispasmodics |
| topic | anthranilic acid hybrid molecules in silico DFT antiproliferative antimicrobial |
| url | https://www.mdpi.com/1422-0067/24/18/13855 |
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