5-Trifluoromethylfuryl derivatives of phosphocarboxylic acids
- Authors: Doronina E.P.1, Pevzner L.M.1, Polukeev V.A.2, Petrov M.L.1
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Affiliations:
- St. Petersburg State Institute of Technology (Technical University)
- Institute of Experimental Medicine
- Issue: Vol 86, No 12 (2016)
- Pages: 2616-2623
- Section: Article
- URL: https://journals.rcsi.science/1070-3632/article/view/216681
- DOI: https://doi.org/10.1134/S1070363216120082
- ID: 216681
Cite item
Abstract
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.
About the authors
E. P. Doronina
St. Petersburg State Institute of Technology (Technical University)
Email: pevzner_lm@list.ru
Russian Federation, Moskovskii pr. 26, St. Petersburg, 190013
L. M. Pevzner
St. Petersburg State Institute of Technology (Technical University)
Author for correspondence.
Email: pevzner_lm@list.ru
Russian Federation, Moskovskii pr. 26, St. Petersburg, 190013
V. A. Polukeev
Institute of Experimental Medicine
Email: pevzner_lm@list.ru
Russian Federation, St. Petersburg
M. L. Petrov
St. Petersburg State Institute of Technology (Technical University)
Email: pevzner_lm@list.ru
Russian Federation, Moskovskii pr. 26, St. Petersburg, 190013