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Sci. Pharm. 2015, 83(4), 549-566; doi:10.3797/scipharm.1506-04

The Effective Synthesis of N-(Arylalkyl)-1-R-4-hydroxy-2,2-dioxo-1H-2λ6,1-benzothiazine-3-carboxamides as Promising Analgesics of a New Chemical Class

1
Department of Pharmaceutical Chemistry, National University of Pharmacy, 53 Pushkinska St., 61002, Kharkiv, Ukraine
2
Department of Pharmaceutical Chemistry, N. I. Pirogov Vinnitsa National Medical University, 56 Pirogov St., Vinnitsa, 21018, Ukraine
3
Department of Pharmaceutical Chemistry, Far Eastern State Medical University, 35 Murav'eva-Amurskogo St., 680000, Khabarovsk, Russia
*
Author to whom correspondence should be addressed.
Received: 14 June 2015 / Accepted: 17 July 2015 / Published: 17 July 2015
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Abstract

A new, effective preparative method has been proposed and the synthesis of a series of N-(arylalkyl)-1-R-4-hydroxy-2,2-dioxo-1H-2λ6,1-benzothiazine-3-car-boxamides has been carried out. It has been shown that amidation of alkyl 1-R-4-hydroxy-2,2-dioxo-1H-2λ6,1-benzothiazine-3-carboxylates with arylalkyl-amines in boiling xylene proceeds with good yield and purity to the corresponding N-(arylalkyl)-amides. However, the presence of water in the reaction mixture has been shown to cause the formation of specific impurities: N-(arylalkyl)-1-R-2,2-dioxo-1H-2λ6,1-benzothiazin-4-amines. According to the results of the pharmacological studies, powerful analgesics have been found among the substances synthesized.
Keywords: Amidation; Analgesia; Arylalkylamines; Synthesis; Pain syndrome; 4-Hydroxy-2,2-dioxo-1,2-dihydro-2λ6,1-benzothiazine-3-carboxamides; 2,1-Benzothiazines Amidation; Analgesia; Arylalkylamines; Synthesis; Pain syndrome; 4-Hydroxy-2,2-dioxo-1,2-dihydro-2λ6,1-benzothiazine-3-carboxamides; 2,1-Benzothiazines
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.; DZYUBENKO, S.P.; SIM, G.; GRINEVICH, L.A. The Effective Synthesis of N-(Arylalkyl)-1-R-4-hydroxy-2,2-dioxo-1H-2λ6,1-benzothiazine-3-carboxamides as Promising Analgesics of a New Chemical Class. Sci. Pharm. 2015, 83, 549-566.

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