Rhodanine derived enethiols react to give 1,3-dithiolanes and mixed disulfides †
Rhodanines have been characterised as ‘difficult to progress’ compounds for medicinal use, though one rhodanine is used for diabetes mellitus treatment and others are in clinical development. Rhodanines can undergo hydrolysis to enethiols which are inhibitors of metallo-enzymes, such as metallo β-la...
| প্রধান লেখক: | , , , |
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| বিন্যাস: | Journal article |
| ভাষা: | English |
| প্রকাশিত: |
Royal Society of Chemistry
2024
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| _version_ | 1826314779633909760 |
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| author | Kamps, JJAG Zhang, D Claridge, TDW Schofield, CJ |
| author_facet | Kamps, JJAG Zhang, D Claridge, TDW Schofield, CJ |
| author_sort | Kamps, JJAG |
| collection | OXFORD |
| description | Rhodanines have been characterised as ‘difficult to progress’ compounds for medicinal use, though one rhodanine is used for diabetes mellitus treatment and others are in clinical development. Rhodanines can undergo hydrolysis to enethiols which are inhibitors of metallo-enzymes, such as metallo β-lactamases. We report that in DMSO, rhodanine derived enethiols undergo dimerisations to give 1,3-dithiolanes and mixed disulfides. The results highlight the potential of rhodanines and enethiols to give multiple products. They suggest that where possible DMSO should be avoided as a storage solvent for rhodanines/enethiols and highlight the need for further research on biologically relevant enethiols/mixed disulfides. |
| first_indexed | 2024-09-25T04:06:19Z |
| format | Journal article |
| id | oxford-uuid:07f4fc6d-cbfc-4e2f-adc7-8b12733baa1f |
| institution | University of Oxford |
| language | English |
| last_indexed | 2024-12-09T03:13:02Z |
| publishDate | 2024 |
| publisher | Royal Society of Chemistry |
| record_format | dspace |
| spelling | oxford-uuid:07f4fc6d-cbfc-4e2f-adc7-8b12733baa1f2024-10-16T09:09:50ZRhodanine derived enethiols react to give 1,3-dithiolanes and mixed disulfides †Journal articlehttp://purl.org/coar/resource_type/c_dcae04bcuuid:07f4fc6d-cbfc-4e2f-adc7-8b12733baa1fEnglishJisc Publications RouterRoyal Society of Chemistry2024Kamps, JJAGZhang, DClaridge, TDWSchofield, CJRhodanines have been characterised as ‘difficult to progress’ compounds for medicinal use, though one rhodanine is used for diabetes mellitus treatment and others are in clinical development. Rhodanines can undergo hydrolysis to enethiols which are inhibitors of metallo-enzymes, such as metallo β-lactamases. We report that in DMSO, rhodanine derived enethiols undergo dimerisations to give 1,3-dithiolanes and mixed disulfides. The results highlight the potential of rhodanines and enethiols to give multiple products. They suggest that where possible DMSO should be avoided as a storage solvent for rhodanines/enethiols and highlight the need for further research on biologically relevant enethiols/mixed disulfides. |
| spellingShingle | Kamps, JJAG Zhang, D Claridge, TDW Schofield, CJ Rhodanine derived enethiols react to give 1,3-dithiolanes and mixed disulfides † |
| title | Rhodanine derived enethiols react to give 1,3-dithiolanes and mixed disulfides † |
| title_full | Rhodanine derived enethiols react to give 1,3-dithiolanes and mixed disulfides † |
| title_fullStr | Rhodanine derived enethiols react to give 1,3-dithiolanes and mixed disulfides † |
| title_full_unstemmed | Rhodanine derived enethiols react to give 1,3-dithiolanes and mixed disulfides † |
| title_short | Rhodanine derived enethiols react to give 1,3-dithiolanes and mixed disulfides † |
| title_sort | rhodanine derived enethiols react to give 1 3 dithiolanes and mixed disulfides † |
| work_keys_str_mv | AT kampsjjag rhodaninederivedenethiolsreacttogive13dithiolanesandmixeddisulfides AT zhangd rhodaninederivedenethiolsreacttogive13dithiolanesandmixeddisulfides AT claridgetdw rhodaninederivedenethiolsreacttogive13dithiolanesandmixeddisulfides AT schofieldcj rhodaninederivedenethiolsreacttogive13dithiolanesandmixeddisulfides |