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Convenient synthesis of C75, an inhibitor of FAS and CPT1
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C75 is a synthetic racemic α-methylene-γ-butyrolactone exhibiting anti-tumoral properties in vitro and in vivo as well as inducing hypophagia and weight loss in rodents. These interesting properties are thought to be a consequence of the inhibition of the key enzymes FAS and CPT1 involved in lipid metabolism. The need for larger amounts of this compound for biological evaluation prompted us to develop a convenient and reliable route to multigram quantities of C75 from easily available ethyl penta-3,4-dienoate 6. A recently described protocol for the addition of 6 to a mixture of dicyclohexylborane and nonanal followed by acidic treatment of the crude afforded lactone 8, as a mixture of cis and trans isomers, in good yield. The DBU-catalyzed isomerization of the methyl esters 9 arising from 8 gave a 10:1 trans/cis mixture from which the trans isomer was isolated and easily transformed into C75. The temporary transformation of C75 into a phenylseleno ether derivative makes its purification, manipulation and storage easier.
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SÁNCHEZ ZARZALEJO, Carolina, MAKOWSKI, Kamil, MERA NANÍN, Paula, FARRÀS I SOLER, Jaume, NICOLÁS GALINDO, Ernesto, HERRERO RODRÍGUEZ, Laura, ASINS MUÑOZ, Guillermina, SERRA I CUCURULL, Dolors, GARCÍA HEGARDT, Fausto, ARIZA PIQUER, Xavier, GARCÍA GÓMEZ, Jordi. Convenient synthesis of C75, an inhibitor of FAS and CPT1. _RSC Advances_. 2013. Vol. 3, núm. 6564-6571. [consulta: 29 de gener de 2026]. ISSN: 2046-2069. [Disponible a: https://hdl.handle.net/2445/43283]