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Sci. Pharm. 2016, 84(3), 523-535; doi:10.3390/scipharm84030523

Synthesis, Structure, and Analgesic Properties of Halogen-Substituted 4-Hydroxy-2,2-dioxo-1H-2λ6,1-benzothiazine-3-carboxanilides

1
Department of Pharmaceutical Chemistry, National University of Pharmacy, 53 Pushkinska St., Kharkiv 61002, Ukraine
2
STC “Institute for Single Crystals”, National Academy of Sciences of Ukraine, 60 Nauki Ave., Kharkiv 61001, Ukraine
3
Department of Inorganic Chemistry, V. N. Karazin Kharkiv National University, 4 Svobody Sq., Kharkiv 61077, Ukraine
4
Department of Pharmaceutical Chemistry, Far Eastern State Medical University, 35 Murav’eva-Amurskogo St., Khabarovsk 680000, Russia
*
Author to whom correspondence should be addressed.
Academic Editor: Thomas Erker
Received: 10 May 2016 / Accepted: 10 June 2016 / Published: 17 June 2016
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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. View Full-Text
Keywords: amidation; analgesia; anilide; synthesis; pain syndrome; 4-hydroxy-2,2-dioxo-1H-2λ6,1-benzothiazine-3-carboxamides; 2,1-benzothiazines amidation; analgesia; anilide; synthesis; pain syndrome; 4-hydroxy-2,2-dioxo-1H-2λ6,1-benzothiazine-3-carboxamides; 2,1-benzothiazines
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This is an open access article distributed under the Creative Commons Attribution License which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited. (CC BY 4.0).

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MDPI and ACS Style

Ukrainets, I.V.; Petrushova, L.A.; Shishkina, S.V.; Sidorenko, L.V.; Sim, G.; Kryvanych, O.V. Synthesis, Structure, and Analgesic Properties of Halogen-Substituted 4-Hydroxy-2,2-dioxo-1H-2λ6,1-benzothiazine-3-carboxanilides. Sci. Pharm. 2016, 84, 523-535.

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