2-{[(4-Hydroxy-3,5-dimethoxyphenyl)methylidene]hydrazinylidene}-4-oxo-1,3-thiazolidin-5-yl Acetic Acid
Thia-Michael addition of 2-[(4-hydroxy-3,5-dimethoxyphenyl)methylidene]hydrazine-1-carbothioamide (1) with maleic anhydride results in the formation of the title compound 2-{[(4-hydroxy-3,5-dimethoxyphenyl)methylidene]hydrazinylidene}-4-oxo-1,3-thiazolidin-5-yl acetic acid 2. The precursor 1 is synt...
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MDPI AG
2018-07-01
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| Series: | Molbank |
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| Online Access: | http://www.mdpi.com/1422-8599/2018/3/M1009 |
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| author | Sangeetha Karanth Badiadka Narayana Sharath Chandra Kodandoor Balladka Kunhanna Sarojini |
| author_facet | Sangeetha Karanth Badiadka Narayana Sharath Chandra Kodandoor Balladka Kunhanna Sarojini |
| author_sort | Sangeetha Karanth |
| collection | DOAJ |
| description | Thia-Michael addition of 2-[(4-hydroxy-3,5-dimethoxyphenyl)methylidene]hydrazine-1-carbothioamide (1) with maleic anhydride results in the formation of the title compound 2-{[(4-hydroxy-3,5-dimethoxyphenyl)methylidene]hydrazinylidene}-4-oxo-1,3-thiazolidin-5-yl acetic acid 2. The precursor 1 is synthesized by the reaction of 4-hydroxy-3,5-dimethoxybenzaldehyde and thiosemicarbazide in the presence of glacial acetic acid as the catalyst. The structure of the title compound is determined by elemental analysis, FT-IR, 1H-NMR, 13C-NMR and mass spectral data. In order to determine the molecular interactions with the bacterial enzyme, the title compound is further docked into the active site of the MurB protein of Staphylococcus aureus (PDB ID: 1HSK). The in vitro antibacterial and antifungal activity of the title compound is carried out in order to appraise its antimicrobial efficacy by determination of zone of inhibition and minimal inhibitory concentration. The compound is also evaluated for its antioxidant property by 2,2-diphenyl-1-picryl-hydrazyl (DPPH) radical scavenging assay. |
| first_indexed | 2024-04-13T09:59:30Z |
| format | Article |
| id | doaj.art-5cab858ce3ac4331b1f9025226e9a74c |
| institution | Directory Open Access Journal |
| issn | 1422-8599 |
| language | English |
| last_indexed | 2024-04-13T09:59:30Z |
| publishDate | 2018-07-01 |
| publisher | MDPI AG |
| record_format | Article |
| series | Molbank |
| spelling | doaj.art-5cab858ce3ac4331b1f9025226e9a74c2022-12-22T02:51:16ZengMDPI AGMolbank1422-85992018-07-0120183M100910.3390/M1009M10092-{[(4-Hydroxy-3,5-dimethoxyphenyl)methylidene]hydrazinylidene}-4-oxo-1,3-thiazolidin-5-yl Acetic AcidSangeetha Karanth0Badiadka Narayana1Sharath Chandra Kodandoor2Balladka Kunhanna Sarojini3Department of Studies in Chemistry, Mangalore University, Mangalagangothri, Karnataka-574199, IndiaDepartment of Studies in Chemistry, Mangalore University, Mangalagangothri, Karnataka-574199, IndiaDepartment of Studies in Biosciences, Mangalore University, Mangalagangothri, Karnataka-574199, IndiaDepartment of Industrial Chemistry, Mangalore University, Mangalagangothri, Karnataka-574199, IndiaThia-Michael addition of 2-[(4-hydroxy-3,5-dimethoxyphenyl)methylidene]hydrazine-1-carbothioamide (1) with maleic anhydride results in the formation of the title compound 2-{[(4-hydroxy-3,5-dimethoxyphenyl)methylidene]hydrazinylidene}-4-oxo-1,3-thiazolidin-5-yl acetic acid 2. The precursor 1 is synthesized by the reaction of 4-hydroxy-3,5-dimethoxybenzaldehyde and thiosemicarbazide in the presence of glacial acetic acid as the catalyst. The structure of the title compound is determined by elemental analysis, FT-IR, 1H-NMR, 13C-NMR and mass spectral data. In order to determine the molecular interactions with the bacterial enzyme, the title compound is further docked into the active site of the MurB protein of Staphylococcus aureus (PDB ID: 1HSK). The in vitro antibacterial and antifungal activity of the title compound is carried out in order to appraise its antimicrobial efficacy by determination of zone of inhibition and minimal inhibitory concentration. The compound is also evaluated for its antioxidant property by 2,2-diphenyl-1-picryl-hydrazyl (DPPH) radical scavenging assay.http://www.mdpi.com/1422-8599/2018/3/M1009Thia-Michael additionmaleic anhydridein vitro antimicrobial evaluationmolecular dockingDPPH radical scavenging assay |
| spellingShingle | Sangeetha Karanth Badiadka Narayana Sharath Chandra Kodandoor Balladka Kunhanna Sarojini 2-{[(4-Hydroxy-3,5-dimethoxyphenyl)methylidene]hydrazinylidene}-4-oxo-1,3-thiazolidin-5-yl Acetic Acid Molbank Thia-Michael addition maleic anhydride in vitro antimicrobial evaluation molecular docking DPPH radical scavenging assay |
| title | 2-{[(4-Hydroxy-3,5-dimethoxyphenyl)methylidene]hydrazinylidene}-4-oxo-1,3-thiazolidin-5-yl Acetic Acid |
| title_full | 2-{[(4-Hydroxy-3,5-dimethoxyphenyl)methylidene]hydrazinylidene}-4-oxo-1,3-thiazolidin-5-yl Acetic Acid |
| title_fullStr | 2-{[(4-Hydroxy-3,5-dimethoxyphenyl)methylidene]hydrazinylidene}-4-oxo-1,3-thiazolidin-5-yl Acetic Acid |
| title_full_unstemmed | 2-{[(4-Hydroxy-3,5-dimethoxyphenyl)methylidene]hydrazinylidene}-4-oxo-1,3-thiazolidin-5-yl Acetic Acid |
| title_short | 2-{[(4-Hydroxy-3,5-dimethoxyphenyl)methylidene]hydrazinylidene}-4-oxo-1,3-thiazolidin-5-yl Acetic Acid |
| title_sort | 2 4 hydroxy 3 5 dimethoxyphenyl methylidene hydrazinylidene 4 oxo 1 3 thiazolidin 5 yl acetic acid |
| topic | Thia-Michael addition maleic anhydride in vitro antimicrobial evaluation molecular docking DPPH radical scavenging assay |
| url | http://www.mdpi.com/1422-8599/2018/3/M1009 |
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