Natural Tetraponerines: A General Synthesis and Antiproliferative Activity
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Campo DC | Valor | Idioma |
---|---|---|
dc.contributor | Catálisis Estereoselectiva en Síntesis Orgánica (CESO) | es |
dc.contributor | Síntesis Asimétrica (SINTAS) | es |
dc.contributor.author | Bosque, Irene | - |
dc.contributor.author | Gonzalez-Gomez, Jose C. | - |
dc.contributor.author | Loza, María Isabel | - |
dc.contributor.author | Brea, José | - |
dc.contributor.other | Universidad de Alicante. Departamento de Química Orgánica | es |
dc.contributor.other | Universidad de Alicante. Instituto Universitario de Síntesis Orgánica | es |
dc.date.accessioned | 2015-04-23T08:14:58Z | - |
dc.date.available | 2015-04-23T08:14:58Z | - |
dc.date.issued | 2014-04-14 | - |
dc.identifier.citation | Journal of Organic Chemistry. 2014, 79(9): 3982-3991. doi:10.1021/jo500446f | es |
dc.identifier.issn | 0022-3263 (Print) | - |
dc.identifier.issn | 1520-6904 (Online) | - |
dc.identifier.uri | http://hdl.handle.net/10045/46330 | - |
dc.description.abstract | A stereocontrolled general methodology to access all natural tetraponerines from (+)-T1 to (+)-T8 is detailed. Two consecutive indium-mediated aminoallylations with the appropriate enantiomer of chiral N-tert-butylsulfinamide and a thermodynamic control at the aminal stereocenter allow the formation of each natural tetraponerine with excellent stereoselectivity. The use of 4-bromobutanal in the first aminoallylation leads to the formation of 5–6–5 tetraponerines, while 5-bromopentanal is required to build the scaffold of 6–6–5 tetraponerines. A cross-metathesis reaction of the second aminoallylation product with cis-3-hexene is used to elongate the side chain up to 5 carbons so as to prepare the tetraponerines T5 to T8. The anticancer activity of these heavier tetraponerines against four different carcinoma human cell lines is examined, observing a promising cytotoxic activity of (+)-T7 against breast carcinoma cell line MCF-7. | es |
dc.description.sponsorship | We thank the Spanish Ministerio de Ciencia e Innovación for their financial support (CTQ2011-24165). I.B. acknowledges the Generalitat Valenciana for a predoctoral fellowship (ACIF/2011/159). | es |
dc.language | eng | es |
dc.publisher | American Chemical Society | es |
dc.rights | © 2014 American Chemical Society | es |
dc.subject | Natural tetraponerines | es |
dc.subject | Synthesis | es |
dc.subject | Antiproliferative | es |
dc.subject.other | Química Orgánica | es |
dc.title | Natural Tetraponerines: A General Synthesis and Antiproliferative Activity | es |
dc.type | info:eu-repo/semantics/article | es |
dc.peerreviewed | si | es |
dc.identifier.doi | 10.1021/jo500446f | - |
dc.relation.publisherversion | http://dx.doi.org/10.1021/jo500446f | es |
dc.rights.accessRights | info:eu-repo/semantics/openAccess | es |
dc.relation.projectID | info:eu-repo/grantAgreement/MICINN//CTQ2011-24165 | - |
Aparece en las colecciones: | INV - SINTAS - Artículos de Revistas INV - CESO - Artículos de Revistas |
Archivos en este ítem:
Archivo | Descripción | Tamaño | Formato | |
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2014_Bosque_etal_JOC_final.pdf | Versión final (acceso restringido) | 1,49 MB | Adobe PDF | Abrir Solicitar una copia |
2014_Bosque_etal_JOC_rev.pdf | Versión revisada (acceso abierto) | 789,57 kB | Adobe PDF | Abrir Vista previa |
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