Design, synthesis and in vitro splicing inhibition of desmethyl and carba-derivatives of herboxidiene
| Autor: | Emilio L. Cárdenas, Nianchun Ma, Arun K. Ghosh, Melissa S. Jurica, Kerstin A. Effenberger, Kai Lv |
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| Rok vydání: | 2016 |
| Předmět: |
0301 basic medicine
Stereochemistry RNA Splicing Stereoisomerism Chemistry Techniques Synthetic Biochemistry Desymmetrization Article 03 medical and health sciences Inhibitory Concentration 50 Medicinal and Biomolecular Chemistry Suzuki reaction Physical and Theoretical Chemistry Pyrans Chemistry Synthetic Organic Chemistry Enantioselective synthesis Chemistry Techniques Desmethyl Boronic Acids In vitro 030104 developmental biology Drug Design RNA splicing Fatty Alcohols Herboxidiene |
| Zdroj: | Organic & biomolecular chemistry, vol 14, iss 23 Ghosh, AK; Lv, K; Ma, N; Cardenas, EL; Effenberger, KA; & Jurica, MS. (2016). Design, synthesis and in vitro splicing inhibition of desmethyl and carba-derivatives of herboxidiene. ORGANIC & BIOMOLECULAR CHEMISTRY, 14(23), 5263-5271. doi: 10.1039/c6ob00725b. UC Santa Cruz: Retrieved from: http://www.escholarship.org/uc/item/5549r8bw |
| DOI: | 10.1039/c6ob00725b. |
| Popis: | Herboxidiene is a potent inhibitor of spliceosomes. It exhibits excellent anticancer activity against multiple human cancer cell lines. Herein, we describe an enantioselective synthesis of a desmethyl derivative and the corresponding carba-derivatives of herboxidiene. The synthesis involved Suzuki coupling of a vinyl iodide with boronate as the key reaction. For the synthesis of carba-derivatives, the corresponding optically active cyclohexane-1,3-dicarbonyl derivatives were synthesized using an enantioselective desymmetrization of meso-anhydride. The biological properties of these derivatives were evaluated in an in vitro splicing assay. |
| Databáze: | OpenAIRE |
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