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Synthesis and antitumour evaluation of benzopsoralen analogues
Oliveira, Ana M. A. G.; Campos, Ana M. F. Oliveira; Rodrigues, Lígia M.; Raposo, M. Manuela M.; Machado, António E. H.; Nascimento, Maria São JoséThe synthesis of five new analogues of benzopsoralens, derived from xanthen-9-one and carbazole is described. The preparation of the hydroxylated precursors, their formylation and the formation of the pyranone ring, by the reaction between ortho-formylated heterocycles and diethyl malonate in EtOH, will be discussed. The inhibitory effect on the growth of human tumour cell lines (MCF-7, SF-268 and NCI-460) of t...
Psoralen analogues : synthesis, inhibitory activity of growth of human tumor ce...
Oliveira, Ana M. A. G.; Campos, Ana M. F. Oliveira; Raposo, M. Manuela M.; Machado, António E. H.; Puapairoj, Prapawadee; Pedro, MadalenaEight psoralens have been evaluated for their ability to inhibit the in vitro growth of three human turner cell lines representing different tumor types, MCF-7 (breast cancer), NCI-14460 (non-small cell lung cancer) and SF-268 (CNS cancer). The synthesis of four new psoralens (benzofur-ocournarins) is presented as well as the results of the ab initio calculations to find the parameters that relate the structure...
Análogos do psolareno com um núcleo de dibenzofurano, xantona ou carbazole : sí...
Oliveira, Ana M. A. G.Tese de doutoramento em Ciências, ramo de Química. ; O uso de fármacos para o tratamento de doenças de pele remonta já ao antigo Egipto. Nesses tratamentos eram usadas plantas, a partir das quais se faziam preparações que eram ingeridas, ou aplicadas na pele dos pacientes que depois se expunham ao Sol. Os psoralenos, também chamados furocumarinas, são produtos provenientes dessas plantas que hoje em dia são pr...
Synthesis of novel carboxylated benzoxazolylcoumarins
Rodrigues, Lígia M.; X. H. Luan; Oliveira, Ana M. A. G.; Campos, Ana M. F. OliveiraSix novel coumarins containing carboxylic ester or acid groups were prepared. The compounds were characterised by the usual methods. In a few cases the fluorescence data were obtained.
Fries rearrangement of dibenzofuran-2-yl ethanoate under photochemical and Lewi...
Campos, Ana M. F. Oliveira; Oliveira, Ana M. A. G.; Raposo, M. Manuela M.; Griffiths, John; Machado, António E. H.The Fries rearrangement of dibenzofuran-2-yl ethanoate as a route to o-hydroxyacetyldibenzofurans has been investigated, both under thermal Lewis-acid catalysed and non-catalysed photochemical conditions. The reactions were examined theoretically at semi-empirical (PM3 and ZINDO/S) and density functional theory (DFT) levels. The correct selection of reaction conditions provides viable preparative routes to orth...
Synthesis of psoralen analogues based on dibenzofuran
Campos, Ana M. F. Oliveira; Oliveira, Ana M. A. G.; Raposo, M. Manuela M.; Griffiths, John; Machado, António E. H.The syntheses of four novel psoralen derivatives, 6a-d, of the benzofurocoumarin (=benzofuro[1]benzopyranone) type containing an ester group are described. These compounds might be of interest in PUVA (psoralen long-wave ultraviolet radiation) therapy. The overall efficiency of the synthetic procedure is greatly limited by the low yields for the penultimate step, i.e. formylation of the dibenzofuranols 3a,c or ...
Synthesis of fluorescent 3-benzoxazol-2-yl-coumarins
X. H. Luan; Cerqueira, N. M. F. S. A.; Oliveira, Ana M. A. G.; Raposo, M. Manuela M.; Rodrigues, Lígia M.; Coelho, Paulo J.; Campos, Ana M. F. OliveiraTwelve 3-benzoxazol-2-yl-coumarins (1-3) were synthesised by reacting various ortho-aminophenols with three coumarin-3-carboxylic acids either directly or by formation of the intermediate amide. The cyclodehydrating agent was polyphosphoric acid (PPA). The compounds were characterised by spectroscopic methods. Absorption and fluorescence spectra of the compounds have also been recorded.
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