Function-Oriented and Modular (+/-)-cis-Pseudoguaianolide Synthesis: Discovery of New Nrf2 Activators and NF-κB Inhibitors.
| Autor: | Emmetiere F; Department of Chemistry, University of Florida, PO Box 117200, Gainesville, FL, 32608, USA., Ratnayake R; Department of Medicinal Chemistry and Center for Natural Products, Drug Discovery and Development (CNPD3), University of Florida, Gainesville, FL, 32610, USA., Schares HAM; Department of Medicinal Chemistry, University of Minnesota, Minneapolis, MN, 55455, USA., Jones KFM; Department of Chemistry, University of Minnesota, Minneapolis, MN, 55455, USA., Bevan-Smith E; Department of Chemistry, University of Florida, PO Box 117200, Gainesville, FL, 32608, USA., Luesch H; Department of Medicinal Chemistry and Center for Natural Products, Drug Discovery and Development (CNPD3), University of Florida, Gainesville, FL, 32610, USA., Harki DA; Department of Medicinal Chemistry, University of Minnesota, Minneapolis, MN, 55455, USA.; Department of Chemistry, University of Minnesota, Minneapolis, MN, 55455, USA., Grenning AJ; Department of Chemistry, University of Florida, PO Box 117200, Gainesville, FL, 32608, USA. |
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| Jazyk: | angličtina |
| Zdroj: | Chemistry (Weinheim an der Bergstrasse, Germany) [Chemistry] 2021 Mar 22; Vol. 27 (17), pp. 5564-5571. Date of Electronic Publication: 2021 Feb 26. |
| DOI: | 10.1002/chem.202100038 |
| Abstrakt: | Described herein is a function-oriented synthesis route and biological evaluation of pseudoguaianolide analogues. The 10-step synthetic route developed retains the topological complexity of the natural product, installs functional handles for late-stage diversification, and forges the key bioactive Michael acceptors early in the synthesis. The analogues were found to be low-micromolar Nrf2 activators and micromolar NF-κB inhibitors and dependent on the local environment of the Michael acceptor moieties. (© 2021 Wiley-VCH GmbH.) |
| Databáze: | MEDLINE |
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