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Sci. Pharm. 2016, 84(3), 497-506; doi:10.3390/scipharm84030497

The Study of Structure—Analgesic Activity Relationships in a Series of 4-Hydroxy-2,2-dioxo-1H-2λ6,1-benzothiazine-3-carboxylic Acid Toluidides and Xylidides

1
Department of Pharmaceutical Chemistry, National University of Pharmacy, 53 Pushkinska St., Kharkiv 61002, Ukraine
2
Department of Pharmaceutical Chemistry, N. I. Pirogov Vinnitsa National Medical University, 56 Pirogov St., Vinnitsa 21018, Ukraine
*
Author to whom correspondence should be addressed.
Academic Editor: Thomas Erker
Received: 27 December 2015 / Accepted: 2 February 2016 / Published: 18 April 2016
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Abstract

In continuing the search for new analgesics among derivatives of 2,1-benzothiazines, a series of corresponding toluidides and xylidides of 4-hydroxy-2,2-dioxo-1H-2λ6,1-benzothiazine-3-carboxylic acid has been synthesized by the reaction of ethyl 4-hydroxy-2,2-dioxo-1H-2λ6,1-benzothiazine-3-carboxylate with equimolar amounts of mono- and dimethyl-substituted anilides in boiling dry xylene. Their structure has been confirmed by the data of elemental analysis, nuclear magnetic resonance (NMR) spectroscopy (1Н and 13С), as well as mass spectrometry. All compounds obtained were subjected to pharmacological screening to identify their analgesic properties. Testing was carried out in male rats using the standard model of the thermal tail-flick (tail immersion test) in parallel and in comparison with the structurally related drugs meloxicam and piroxicam. Among the substances studied, highly active oral painkillers have been found; they exceed the analgesic effect of the reference drugs using the same dose. Interesting structural and biological regularities have been described; they will be useful in further research on creating promising new analgesics based on 4-hydroxy-2,2-dioxo-1H-2λ6,1-benzothiazine-3-carboxamides. View Full-Text
Keywords: amidation; analgesia; anilides; synthesis; pain syndrome; 4-hydroxy-2,2-dioxo-1H-2λ6,1-benzothiazine-3-carboxamides; 2,1-benzothiazines amidation; analgesia; anilides; 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.; Sidorenko, L.V.; Davidenko, A.A.; Duchenko, M.A. The Study of Structure—Analgesic Activity Relationships in a Series of 4-Hydroxy-2,2-dioxo-1H-2λ6,1-benzothiazine-3-carboxylic Acid Toluidides and Xylidides. Sci. Pharm. 2016, 84, 497-506.

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