5-[4-(<i>tert</i>-Butyl)cyclohexylidene]-2-thioxothiazolidin-4-one
The Knoevenagel reaction is an essential synthetic tool in the organic and medicinal chemistry of thiazolidin-4-one derivatives. In the present work, the application of ethylenediamine diacetate (EDDA) as an effective catalyst for the interaction of 2-thioxothiazolidin-4-one with 4-(<i>tert<...
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MDPI AG
2021-09-01
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| Series: | Molbank |
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| Online Access: | https://www.mdpi.com/1422-8599/2021/4/M1281 |
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| author | Serhii Holota Andrii Lozynskyi Yulian Konechnyi Yulia Shepeta Roman Lesyk |
| author_facet | Serhii Holota Andrii Lozynskyi Yulian Konechnyi Yulia Shepeta Roman Lesyk |
| author_sort | Serhii Holota |
| collection | DOAJ |
| description | The Knoevenagel reaction is an essential synthetic tool in the organic and medicinal chemistry of thiazolidin-4-one derivatives. In the present work, the application of ethylenediamine diacetate (EDDA) as an effective catalyst for the interaction of 2-thioxothiazolidin-4-one with 4-(<i>tert</i>-butyl)cyclohexanone is proposed. The structure of novel synthesized 5-[4-(<i>tert</i>-butyl)cyclohexylidene]-2-thioxothiazolidin-4-one (yield 61%) was confirmed by <sup>1</sup>H-, <sup>13</sup>C-NMR, LC-MS, IR, and UV spectra. Drug-like properties of the synthesized compound were evaluated <i>in silico</i> using the SwissAdme, and their potential antimicrobial activity against 15 strains of Gram-positive and Gram-negative bacteria as well as yeasts was evaluated <i>in vitro</i>. The synthesized compound possesses satisfactory drug-like parameters and promising antimicrobial properties and presents interest as a prospective intermediate for the forthcoming design of biologically active small molecules. |
| first_indexed | 2024-03-10T03:30:04Z |
| format | Article |
| id | doaj.art-3848270137794d8c91e78d0bde3a43d6 |
| institution | Directory Open Access Journal |
| issn | 1422-8599 |
| language | English |
| last_indexed | 2024-03-10T03:30:04Z |
| publishDate | 2021-09-01 |
| publisher | MDPI AG |
| record_format | Article |
| series | Molbank |
| spelling | doaj.art-3848270137794d8c91e78d0bde3a43d62023-11-23T09:43:19ZengMDPI AGMolbank1422-85992021-09-0120214M128110.3390/M12815-[4-(<i>tert</i>-Butyl)cyclohexylidene]-2-thioxothiazolidin-4-oneSerhii Holota0Andrii Lozynskyi1Yulian Konechnyi2Yulia Shepeta3Roman Lesyk4Department of Pharmaceutical, Organic and Bioorganic Chemistry, Danylo Halytsky Lviv National Medical University, Pekarska 69, 79010 Lviv, UkraineDepartment of Pharmaceutical, Organic and Bioorganic Chemistry, Danylo Halytsky Lviv National Medical University, Pekarska 69, 79010 Lviv, UkraineDepartment of Microbiology, Danylo Halytsky Lviv National Medical University, Pekarska 69, 79010 Lviv, UkraineDepartment of Pharmaceutical Chemistry, National Pirogov Memorial Medical University, Pirogov 56, 21018 Vinnytsya, UkraineDepartment of Pharmaceutical, Organic and Bioorganic Chemistry, Danylo Halytsky Lviv National Medical University, Pekarska 69, 79010 Lviv, UkraineThe Knoevenagel reaction is an essential synthetic tool in the organic and medicinal chemistry of thiazolidin-4-one derivatives. In the present work, the application of ethylenediamine diacetate (EDDA) as an effective catalyst for the interaction of 2-thioxothiazolidin-4-one with 4-(<i>tert</i>-butyl)cyclohexanone is proposed. The structure of novel synthesized 5-[4-(<i>tert</i>-butyl)cyclohexylidene]-2-thioxothiazolidin-4-one (yield 61%) was confirmed by <sup>1</sup>H-, <sup>13</sup>C-NMR, LC-MS, IR, and UV spectra. Drug-like properties of the synthesized compound were evaluated <i>in silico</i> using the SwissAdme, and their potential antimicrobial activity against 15 strains of Gram-positive and Gram-negative bacteria as well as yeasts was evaluated <i>in vitro</i>. The synthesized compound possesses satisfactory drug-like parameters and promising antimicrobial properties and presents interest as a prospective intermediate for the forthcoming design of biologically active small molecules.https://www.mdpi.com/1422-8599/2021/4/M1281Knoevenagel reactionrhodaninecatalystethylenediamine diacetate (EDDA)antimicrobial activity |
| spellingShingle | Serhii Holota Andrii Lozynskyi Yulian Konechnyi Yulia Shepeta Roman Lesyk 5-[4-(<i>tert</i>-Butyl)cyclohexylidene]-2-thioxothiazolidin-4-one Molbank Knoevenagel reaction rhodanine catalyst ethylenediamine diacetate (EDDA) antimicrobial activity |
| title | 5-[4-(<i>tert</i>-Butyl)cyclohexylidene]-2-thioxothiazolidin-4-one |
| title_full | 5-[4-(<i>tert</i>-Butyl)cyclohexylidene]-2-thioxothiazolidin-4-one |
| title_fullStr | 5-[4-(<i>tert</i>-Butyl)cyclohexylidene]-2-thioxothiazolidin-4-one |
| title_full_unstemmed | 5-[4-(<i>tert</i>-Butyl)cyclohexylidene]-2-thioxothiazolidin-4-one |
| title_short | 5-[4-(<i>tert</i>-Butyl)cyclohexylidene]-2-thioxothiazolidin-4-one |
| title_sort | 5 4 i tert i butyl cyclohexylidene 2 thioxothiazolidin 4 one |
| topic | Knoevenagel reaction rhodanine catalyst ethylenediamine diacetate (EDDA) antimicrobial activity |
| url | https://www.mdpi.com/1422-8599/2021/4/M1281 |
| work_keys_str_mv | AT serhiiholota 54itertibutylcyclohexylidene2thioxothiazolidin4one AT andriilozynskyi 54itertibutylcyclohexylidene2thioxothiazolidin4one AT yuliankonechnyi 54itertibutylcyclohexylidene2thioxothiazolidin4one AT yuliashepeta 54itertibutylcyclohexylidene2thioxothiazolidin4one AT romanlesyk 54itertibutylcyclohexylidene2thioxothiazolidin4one |