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2013-04-17

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Si us plau utilitzeu sempre aquest identificador per citar o enllaçar aquest document: https://hdl.handle.net/2445/43283

Convenient synthesis of C75, an inhibitor of FAS and CPT1

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Recurs relacionat

http://dx.doi.org/10.1039/C3RA40913A

Resum

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.

Matèries

Inhibidors enzimàtics, Trastorns del metabolisme dels lípids, Càncer, Diabetis, Aprimament

Matèries (anglès)

Enzyme inhibitors, Lipid metabolism disorders, Cancer, Diabetes, Weight loss

Citació

Col·leccions

Articles publicats en revistes (Química Inorgànica i Orgànica)

Citació

SÁNCHEZ ZARZALEJO, Carolina, et al. Convenient synthesis of C75, an inhibitor of FAS and CPT1. RSC Advances. 2013. Vol. 3, num. 6564-6571. ISSN 2046-2069. [consulted: 9 of August of 2026]. Available at: https://hdl.handle.net/2445/43283

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