5-Trifluoromethylfuryl derivatives of phosphocarboxylic acids
- Autores: Doronina E.1, Pevzner L.1, Polukeev V.2, Petrov M.1
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Afiliações:
- St. Petersburg State Institute of Technology (Technical University)
- Institute of Experimental Medicine
- Edição: Volume 86, Nº 12 (2016)
- Páginas: 2616-2623
- Seção: Article
- URL: https://journals.rcsi.science/1070-3632/article/view/216681
- DOI: https://doi.org/10.1134/S1070363216120082
- ID: 216681
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Resumo
Methods of synthesis of trifluoromethylfuryl derivatives of phosphonocarboxylic acids are studied. By addition of diethyl hydrogen phosphite to alkyl 3-(5-trifluoromethylfur-2-yl)acrylate under the conditions of the Pudovik reaction the corresponding derivative of 3-phosphonopropionic acid was prepared. Diethyl (5-trifluoromethylfur-2-yl)methanephosphonate in presence of potassium tert-butylate reacts with ethyl acrylate to form trifluoromethylfuryl derivative of 4-phosphonobutyric or 4-phosphonopimelic acid depending on the reaction conditions. In the products of reaction of the alkyl 3-(5-trifluoromethylfur-2-yl)-3-(diethoxyphosphoryl) propionate with ethyl acrylate in the presence of potassium tert-butylate formation of trifluoromethylfuryl derivative of the 3-phosphonoadipic acid is detected. 3-(5-Trifluoromethylfur-2-yl)-3-(diethoxyphosphoryl) propionic acid and its acid chloride are synthesized. The latter compound is used for acylation of glycine to form the corresponding N-acyl derivative. It is suggested that such compounds may be transported in the cell using usual channels of transportation of the amino acids and short peptides.
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Sobre autores
E. Doronina
St. Petersburg State Institute of Technology (Technical University)
Email: pevzner_lm@list.ru
Rússia, Moskovskii pr. 26, St. Petersburg, 190013
L. Pevzner
St. Petersburg State Institute of Technology (Technical University)
Autor responsável pela correspondência
Email: pevzner_lm@list.ru
Rússia, Moskovskii pr. 26, St. Petersburg, 190013
V. Polukeev
Institute of Experimental Medicine
Email: pevzner_lm@list.ru
Rússia, St. Petersburg
M. Petrov
St. Petersburg State Institute of Technology (Technical University)
Email: pevzner_lm@list.ru
Rússia, Moskovskii pr. 26, St. Petersburg, 190013