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http://hdl.handle.net/2445/43283
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DC Field | Value | Language |
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dc.contributor.author | Sánchez Zarzalejo, Carolina | - |
dc.contributor.author | Makowski, Kamil | - |
dc.contributor.author | Mera Nanín, Paula | - |
dc.contributor.author | Farràs i Soler, Jaume | - |
dc.contributor.author | Nicolás Galindo, Ernesto | - |
dc.contributor.author | Herrero Rodríguez, Laura | - |
dc.contributor.author | Asins Muñoz, Guillermina | - |
dc.contributor.author | Serra i Cucurull, Dolors | - |
dc.contributor.author | García Hegardt, Fausto | - |
dc.contributor.author | Ariza Piquer, Xavier | - |
dc.contributor.author | García Gómez, Jordi | - |
dc.date.accessioned | 2013-05-10T07:45:38Z | - |
dc.date.available | 2014-04-17T22:02:18Z | - |
dc.date.issued | 2013-04-17 | - |
dc.identifier.issn | 2046-2069 | - |
dc.identifier.uri | http://hdl.handle.net/2445/43283 | - |
dc.description.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. | - |
dc.format.extent | 18 p. | - |
dc.format.mimetype | application/pdf | - |
dc.language.iso | eng | - |
dc.publisher | Royal Society of Chemistry | - |
dc.relation.isformatof | Versió postprint del document publicat a: http://dx.doi.org/10.1039/C3RA40913A | - |
dc.relation.ispartof | RSC Advances, 2013, vol. 3, p. 6564-6571 | - |
dc.relation.uri | http://dx.doi.org/10.1039/C3RA40913A | - |
dc.rights | (c) Sánchez Zarzalejo, Carolina et al., 2013 | - |
dc.source | Articles publicats en revistes (Química Inorgànica i Orgànica) | - |
dc.subject.classification | Inhibidors enzimàtics | - |
dc.subject.classification | Trastorns del metabolisme dels lípids | - |
dc.subject.classification | Càncer | - |
dc.subject.classification | Diabetis | - |
dc.subject.classification | Aprimament | - |
dc.subject.other | Enzyme inhibitors | - |
dc.subject.other | Lipid metabolism disorders | - |
dc.subject.other | Cancer | - |
dc.subject.other | Diabetes | - |
dc.subject.other | Weight loss | - |
dc.title | Convenient synthesis of C75, an inhibitor of FAS and CPT1 | eng |
dc.type | info:eu-repo/semantics/article | - |
dc.type | info:eu-repo/semantics/acceptedVersion | - |
dc.identifier.idgrec | 620555 | - |
dc.date.updated | 2013-05-07T14:30:04Z | - |
dc.rights.accessRights | info:eu-repo/semantics/openAccess | - |
Appears in Collections: | Articles publicats en revistes (Química Inorgànica i Orgànica) |
Files in This Item:
File | Description | Size | Format | |
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620555.pdf | 467.45 kB | Adobe PDF | View/Open |
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