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https://hdl.handle.net/1822/22511
Título: | The condensation of salicylaldehydes and malononitrile revisited : synthesis of new dimeric chromene derivatives |
Autor(es): | Costa, Marta Sílvia Freitas da Areias, F. Abrunhosa, Luís Venâncio, Armando Proença, M. Fernanda R. P. |
Data: | 2008 |
Editora: | American Chemical Society (ACS) |
Revista: | Journal of Organic Chemistry |
Resumo(s): | The reaction of salicylic aldehydes with malononitrile was reinvestigated, and the reaction pathway was followed by 1H NMR spectroscopy. A delicate control of the experimental conditions allowed the synthesis of 2-imino-2H-chromene-3-carbonitriles 1, (2-amino-3-cyano-4H-chromen-4-yl)malononitriles 2, 4-amino-5-imino-2,7-dimethoxy-5H-chromeno[3,4-c]pyridine-1-carbonitrile 12, and (4,5-diamino-1-cyano-1,10b-dihydro-2H-chromeno[3,4-c]pyridin-2-ylidene)malononitrile 13. Two novel 2-iminochromene dimers, with structures 8 and 9, were isolated and fully characterized. The activity of compound 8a on Aspergillus spp. growth and on ochratoxin A production was evaluated. The results of the bioassays indicate that compound 8a, applied at concentrations of 2 mM, totally inhibited the growth of the fungi tested. Ochratoxin A production by Aspergillus alliaceus was reduced by about 93% with a 200 μM solution of this compound. A moderate inhibitory effect was observed for the analogous structure 8b, and no inhibition was registered for compounds 2 and 1, used as synthetic precursors of the dimeric species 8. |
Tipo: | Artigo |
URI: | https://hdl.handle.net/1822/22511 |
DOI: | 10.1021/jo702552f |
ISSN: | 0022-3263 1520-6904 |
Versão da editora: | http://pubs.acs.org/ |
Arbitragem científica: | yes |
Acesso: | Acesso aberto |
Aparece nas coleções: | CEB - Publicações em Revistas/Séries Internacionais / Publications in International Journals/Series |
Ficheiros deste registo:
Ficheiro | Descrição | Tamanho | Formato | |
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jo702552f.pdf | 216,32 kB | Adobe PDF | Ver/Abrir |