Synthesis, Structure, and Analgesic Properties of Halogen-Substituted
Igor V Ukrainets1, Lidiya A Petrushova2, Svitlana V Shishkina3,4
1Department of Pharmaceutical Chemistry, National University of Pharmacy, 53 Pushkinska St., Kharkiv 61002, Ukraine. uiv-2@mail.ru.
Abstract:
As potential new analgesics, the corresponding 4-hydroxy-2,2-dioxo-1H-2λ⁶,1-benzothiazine-3-carboxanilides have been obtained by amidation of ethyl 4-hydroxy-2,2-dioxo-1H-2λ⁶,1-benzothiazine-3-carboxylate with aniline and its halogenated analogsin boiling dry xylene. The peculiarities of the mass and nuclear magnetic resonance (¹Н and 13С) spectra of the synthesized compounds are discussed. Using X-ray diffraction analysis, the ability of the compounds to form stable solvates with N,N-dimethylformamide has been shown on the example of 4-bromo-substituted derivative. It should be further studied to be considered in their crystallization. According to the results of the pharmacological testing conducted on the model of the thermal tail-flick (tail immersion test) among halogen-substituted 4-hydroxy-2,2-dioxo-1H-2λ⁶,1-benzothiazine-3-carboxanilides, substances which are considerably superior to meloxicam and piroxicam by their analgesic activity have been found. They are of interest for further profound studies.
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