Ya. V. Burgart, I. V. Shchur, E. V. Shchegolkov, V. I. Saloutin, “Synthesis and biological activity of polyfluorinated <i>p</i>-aminosalicylic acids and their amides”, Mendeleev Commun., 2020, Volume 30, Issue 5,Pages <nobr>636

This article is cited in 7 papers

Communications

Synthesis and biological activity of polyfluorinated p-aminosalicylic acids and their amides

Ya. V. Burgart^ab, I. V. Shchur^a, E. V. Shchegolkov^ab, V. I. Saloutin^ab

^a I.Ya. Postovsky Institute of Organic Synthesis, Ural Branch of the Russian Academy of Sciences, Ekaterinburg, Russian Federation
^b Institute of Chemical Engineering, Ural Federal University, Ekaterinburg, Russian Federation

Abstract: Polyfluorinated analogues of salicylamide and p-aminosalicylic acid have been synthesized based on methyl polyfluorosalicylates. Polyfluorosalicylamides were obtained by the reaction with aqueous ammonia, while 4-aminopolyfluorosalicylic acids were prepared in two steps via regio-oriented nucleophilic replacement of para-positioned fluorine atom with azido group followed by its reduction. 3,4,5-Trifluorosalicylamide showed pronounced analgesic in vivo activity in hot plate test while 4-amino-3,5-difluorosalicylic acid revealed high tuberculostatic activity.

Keywords: salicylamide, p-aminosalicylic acid, polyfluoroarenes, organofluorine compounds, aromatic nucleophilic substitution, tuberculostatic activity, analgesic activity, acute toxicity.

Language: English

DOI: 10.1016/j.mencom.2020.09.028

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