3,4-Dihalo-5-hydroxy-2(5<i>H</i>)-furanones: Highly Reactive Small Molecules
3,4-Dichloro-5-hydroxy-2(5<i>H</i>)-furanone and its dibromo analog are highly reactive molecules. Both are members of the 2(5<i>H</i>)-furanone family, which are important as pharmacophores present in drugs and natural products. Compounds possessing the 2(5<i>H</i&g...
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MDPI AG
2024-10-01
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| author | Katarzyna Żurawska Anna Byczek-Wyrostek Anna Kasprzycka Krzysztof Walczak |
| author_facet | Katarzyna Żurawska Anna Byczek-Wyrostek Anna Kasprzycka Krzysztof Walczak |
| author_sort | Katarzyna Żurawska |
| collection | DOAJ |
| description | 3,4-Dichloro-5-hydroxy-2(5<i>H</i>)-furanone and its dibromo analog are highly reactive molecules. Both are members of the 2(5<i>H</i>)-furanone family, which are important as pharmacophores present in drugs and natural products. Compounds possessing the 2(5<i>H</i>)-furanone skeleton isolated from plants and marine organisms exhibit bioactivity against various microorganisms and viruses and can also be used in other medical treatments. The structures of these 3,4-dihalo-2(5<i>H</i>)-furanones cause their high reactivity due to the presence of a carbonyl group on the C2 carbon conjugated with a double bond and a hydroxyl group on the C5 carbon. Two labile halogen atoms on carbons 3 and 4 offer additional possibilities for the introduction of other substituents. These structural features make 3,4-dihalo-5-hydroxy-2(5<i>H</i>)-furanones versatile reactants in chemical synthesis. In this review, we present methods of 3,4-dihalo-5-hydroxy-2(5<i>H</i>)-furanone synthesis, their applications as substrates in various chemical transformations, and examples of their biologically active derivatives. |
| format | Article |
| id | doaj-art-1e59e1e2ea6d4f22aa3ce32b648f4438 |
| institution | Kabale University |
| issn | 1420-3049 |
| language | English |
| publishDate | 2024-10-01 |
| publisher | MDPI AG |
| record_format | Article |
| series | Molecules |
| spelling | doaj-art-1e59e1e2ea6d4f22aa3ce32b648f44382024-11-08T14:38:29ZengMDPI AGMolecules1420-30492024-10-012921514910.3390/molecules292151493,4-Dihalo-5-hydroxy-2(5<i>H</i>)-furanones: Highly Reactive Small MoleculesKatarzyna Żurawska0Anna Byczek-Wyrostek1Anna Kasprzycka2Krzysztof Walczak3Centre of Biotechnology, Silesian University of Technology, Krzywoustego 8, 44-100 Gliwice, PolandCentre of Biotechnology, Silesian University of Technology, Krzywoustego 8, 44-100 Gliwice, PolandCentre of Biotechnology, Silesian University of Technology, Krzywoustego 8, 44-100 Gliwice, PolandDepartment of Organic Chemistry, Bioorganic Chemistry and Biotechnology, Silesian University of Technology, Krzywoustego 4, 44-100 Gliwice, Poland3,4-Dichloro-5-hydroxy-2(5<i>H</i>)-furanone and its dibromo analog are highly reactive molecules. Both are members of the 2(5<i>H</i>)-furanone family, which are important as pharmacophores present in drugs and natural products. Compounds possessing the 2(5<i>H</i>)-furanone skeleton isolated from plants and marine organisms exhibit bioactivity against various microorganisms and viruses and can also be used in other medical treatments. The structures of these 3,4-dihalo-2(5<i>H</i>)-furanones cause their high reactivity due to the presence of a carbonyl group on the C2 carbon conjugated with a double bond and a hydroxyl group on the C5 carbon. Two labile halogen atoms on carbons 3 and 4 offer additional possibilities for the introduction of other substituents. These structural features make 3,4-dihalo-5-hydroxy-2(5<i>H</i>)-furanones versatile reactants in chemical synthesis. In this review, we present methods of 3,4-dihalo-5-hydroxy-2(5<i>H</i>)-furanone synthesis, their applications as substrates in various chemical transformations, and examples of their biologically active derivatives.https://www.mdpi.com/1420-3049/29/21/51492(5<i>H</i>)-furanonenucleophilic substitutionbioactivityanticancer compoundsring transformation |
| spellingShingle | Katarzyna Żurawska Anna Byczek-Wyrostek Anna Kasprzycka Krzysztof Walczak 3,4-Dihalo-5-hydroxy-2(5<i>H</i>)-furanones: Highly Reactive Small Molecules Molecules 2(5<i>H</i>)-furanone nucleophilic substitution bioactivity anticancer compounds ring transformation |
| title | 3,4-Dihalo-5-hydroxy-2(5<i>H</i>)-furanones: Highly Reactive Small Molecules |
| title_full | 3,4-Dihalo-5-hydroxy-2(5<i>H</i>)-furanones: Highly Reactive Small Molecules |
| title_fullStr | 3,4-Dihalo-5-hydroxy-2(5<i>H</i>)-furanones: Highly Reactive Small Molecules |
| title_full_unstemmed | 3,4-Dihalo-5-hydroxy-2(5<i>H</i>)-furanones: Highly Reactive Small Molecules |
| title_short | 3,4-Dihalo-5-hydroxy-2(5<i>H</i>)-furanones: Highly Reactive Small Molecules |
| title_sort | 3 4 dihalo 5 hydroxy 2 5 i h i furanones highly reactive small molecules |
| topic | 2(5<i>H</i>)-furanone nucleophilic substitution bioactivity anticancer compounds ring transformation |
| url | https://www.mdpi.com/1420-3049/29/21/5149 |
| work_keys_str_mv | AT katarzynazurawska 34dihalo5hydroxy25ihifuranoneshighlyreactivesmallmolecules AT annabyczekwyrostek 34dihalo5hydroxy25ihifuranoneshighlyreactivesmallmolecules AT annakasprzycka 34dihalo5hydroxy25ihifuranoneshighlyreactivesmallmolecules AT krzysztofwalczak 34dihalo5hydroxy25ihifuranoneshighlyreactivesmallmolecules |