Synthesis of 2-Thio-Substituted 1,6-Diazabicyclo[3.2.1]octane Derivatives, Potent β-Lactamase Inhibitors
In: The Journal of Organic Chemistry, Jg. 85 (2020-07-08), S. 9650-9660
Online
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Zugriff:
Approval of avibactam by the FDA has led to the recognition of 1,6-diazabicyclo[3.2.1]octane (DBO) derivatives as attractive compounds for β-lactamase inhibition. We achieved a concise and collective synthesis of 2-thio-substituted DBO derivatives. The synthesis involves diastereoselective photo-induced Barton decarboxylative thiolation, which can be applied to large-scale synthesis. The DBO analogues exhibited strong inhibitory activities against serine β-lactamases and acceptable solution stabilities for clinical development.
| Titel: |
Synthesis of 2-Thio-Substituted 1,6-Diazabicyclo[3.2.1]octane Derivatives, Potent β-Lactamase Inhibitors
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| Autor/in / Beteiligte Person: | Sato, Jun ; Yamawaki, Kenji ; Shibuya, Satoru ; Sato, Soichiro ; Ogawa, Masayoshi ; Fujiu, Motohiro ; Yokoo, Katsuki ; Aoki, Toshiaki ; Kusano, Hiroki ; Komano, Kazuo |
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| Zeitschrift: | The Journal of Organic Chemistry, Jg. 85 (2020-07-08), S. 9650-9660 |
| Veröffentlichung: | American Chemical Society (ACS), 2020 |
| Medientyp: | unknown |
| ISSN: | 1520-6904 (print) ; 0022-3263 (print) |
| DOI: | 10.1021/acs.joc.0c00980 |
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