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Title: Convenient synthesis of C75, an inhibitor of FAS and CPT1
Author: 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
Keywords: Inhibidors enzimàtics
Trastorns del metabolisme dels lípids
Enzyme inhibitors
Lipid metabolism disorders
Weight loss
Issue Date: 17-Apr-2013
Publisher: Royal Society of Chemistry
Abstract: 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.
Note: Versió postprint del document publicat a:
It is part of: RSC Advances, 2013, vol. 3, p. 6564-6571
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ISSN: 2046-2069
Appears in Collections:Articles publicats en revistes (Química Inorgànica i Orgànica)

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