https://repositorio.ufba.br/handle/ri/5814
Tipo: | Artigo de Periódico |
Título: | New iodine derivatives of flavonol and isoflavone |
Título(s) alternativo(s): | Anais da Academia Brasileira de Ciências |
Autor(es): | Carvalho, Mário Geraldo de Silva, Virginia C. da Silva, Tânia Maria Sarmento da Camara, Celso de Amorim Braz Filho, Raimundo |
Autor(es): | Carvalho, Mário Geraldo de Silva, Virginia C. da Silva, Tânia Maria Sarmento da Camara, Celso de Amorim Braz Filho, Raimundo |
Abstract: | The reaction of the flavonol 3,7,3', 4'-tetra-O-methylquercetin (1) and of the isoflavone 7,4'-di-O-methylgenistein (2) with alkaline iodine in methanol afforded four new iodine derivatives: 8-iodo-5-hydroxy-3,7,3', 4'-tetramethoxy- flavone (1a) and 6-iodo-5-hydroxy-3,7,3', 4'-tetramethoxyflavone (1b) from 1; 2 afforded a mixture of two compounds, identified as a racemic mixture of (±)-trans-5-hydroxy-2,3,7,4'-tetramethoxy-8-iodo-isoflavanone (2a) and (±)-trans-5-hydroxy-2,3,7,4'-tetramethoxy-6,8-diiodo-isoflavanone (2b). The formation of these different products reveals a significant difference involving the chemical interaction between the reactive site of α, β-unsaturated ketones of flavonol and isoflavone under the tested reaction conditions (using I2/KOH/MeOH). Furthermore, the trans stereo selectivity is noteworthy in the nucleophylic addition of methanol at the isoflavone α, β-unsaturated system. The structures were identified on the basis of spectral data, mainly 1D and 2D NMR and mass spectra. |
Palavras-chave: | Flavonol Isoflavone Iodoflavonoid Iodoisoflavonoid Iodine derivatives |
URI: | http://www.repositorio.ufba.br/ri/handle/ri/5814 |
Data do documento: | 2009 |
Aparece nas coleções: | Artigo Publicado em Periódico (Química) |
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