Conformational analysis of the potential anticancer agent ethyl trihydroxycinnamate - A combined raman spectroscopy and ab initio study

• Tipo: Artigo em Revista Científica Internacional
• Data: 2006

Autores

Sousa, Joana B. (Autor) FCUP; Calheiros, Rita (Autor) Outra; Rio, Vitor (Autor) Outra; Borges, Fernanda Fernanda M (Autor) FFUP; Marques, Maria Paula Matos (Autor) Outra

Revista

Título: Journal of Molecular Structure

Vol. 783

Páginas: 122-135

ISSN: 0022-2860

Editora: Elsevier

Indexação

ISI Web of Knowledge - 18 Citações

Scopus - 18 Citações

Outras Informações

ID Authenticus: P-004-NA6

DOI: 10.1016/j.molstruc.2005.09.004

Abstract (EN): A confon-national analysis of ethyl 3-(3,4,5-trihydroxyphenyl)-2-propenoate (ethyl 3,4,5-trihydroxycinnamate, ETHPPE), a polyphenolic cinnarnic ester which displays antiproliferative activity towards human adenocarcinorna cells, was carried out by Raman spectroscopy coupled to ab initio MO calculations. Apart from the optimised geometrical parameters for the most stable conformations of this compound (both for the trans and cis isomers), the corresponding harmonic vibrational frequencies were obtained. Eighteen distinct geometries were found, 12 for the lowest energy trans isomer and six for the cis species. The conformational preferences of this system were verified to be mainly ruled by the stabilising effect of pi-electron delocalisation, a planar geometry being favoured. The orientation of the ester moiety showed to be the most determinant factor for the overall stability of the molecule. In the light of these results, a complete assignment of the corresponding Raman pattern was performed. (c) 2005 Elsevier B.V. All rights reserved.

Idioma: Inglês

Tipo (Avaliação Docente): Científica