Tiamas, Shelly Gapil and Audet, Florian and Samra, Alma Abou and Bignon, Jérome and Litaudon, Marc and Fourneau, Christophe and Ariffin, Azhar and Awang, Khalijah and Desrat, Sandy and Roussi, Fanny (2018) Asymmetric Total Synthesis and Biological Evaluation of Proapoptotic Natural Myrcene-Derived Cyclohexenyl Chalcones. European Journal of Organic Chemistry, 2018 (42). pp. 5830-5835. ISSN 1434-193X, DOI https://doi.org/10.1002/ejoc.201800262.
Full text not available from this repository.Abstract
Based on a bioinspired asymmetric Diels–Alder cycloaddition using a chiral Evans oxazolidinone, the first total synthesis of both enantiomers of two myrcene-derived cyclohexenyl chalcones, fislatifolione and fislatifolic acid, has been carried out. This strategy was also applied to the total synthesis of nicolaiodesin C. These natural products, as well as their synthetic intermediates, were evaluated by in-vitro affinity displacement assays, based on the modulation of Bcl-xL/Bak, Mcl-1/Bid, and Bcl-2-Bim interactions. This study showed that (+)-fislatifolic acid acts as a dual Bcl-xL/Mcl-1 inhibitor with micromolar activity, and that a Weinreb amide intermediate acts as an excellent Mcl-1/Bcl-2 dual inhibitor at the submicromolar level.
| Item Type: | Article |
|---|---|
| Funders: | UNSPECIFIED |
| Uncontrolled Keywords: | Asymmetric synthesis; Biological activity; Chiral auxiliaries; Cycloaddition; Natural products; Total synthesis |
| Subjects: | Q Science > Q Science (General) Q Science > QD Chemistry |
| Divisions: | Faculty of Science > Department of Chemistry |
| Depositing User: | Ms. Juhaida Abd Rahim |
| Date Deposited: | 25 Feb 2019 03:38 |
| Last Modified: | 25 Feb 2019 03:38 |
| URI: | http://eprints.um.edu.my/id/eprint/20469 |
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