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Volume 83
Issue 4
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Article

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

by
Igor V. UKRAINETS
1,*,
Lidiya A. PETRUSHOVA
1,
Sergiy P. DZYUBENKO
2,
Galina SIM
3 and
Lina A. GRINEVICH
1
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.
Sci. Pharm. 2015, 83(4), 549-566; https://doi.org/10.3797/scipharm.1506-04
Submission received: 14 June 2015 / Accepted: 17 July 2015 / Published: 17 July 2015
Versions Notes

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

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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. https://doi.org/10.3797/scipharm.1506-04

AMA Style

UKRAINETS IV, PETRUSHOVA LA, DZYUBENKO SP, SIM G, GRINEVICH LA. 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. Scientia Pharmaceutica. 2015; 83(4):549-566. https://doi.org/10.3797/scipharm.1506-04

Chicago/Turabian Style

UKRAINETS, Igor V., Lidiya A. PETRUSHOVA, Sergiy P. DZYUBENKO, Galina SIM, and Lina A. GRINEVICH. 2015. "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" Scientia Pharmaceutica 83, no. 4: 549-566. https://doi.org/10.3797/scipharm.1506-04

APA Style

UKRAINETS, I. V., PETRUSHOVA, L. A., DZYUBENKO, S. P., SIM, G., & GRINEVICH, L. A. (2015). 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. Scientia Pharmaceutica, 83(4), 549-566. https://doi.org/10.3797/scipharm.1506-04

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