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Title: Two pseudo-enantiomeric forms of N -benzyl-4-hydroxy-1 methyl-2,2-dioxo-1 H -2λ6,1-benzothiazine-3-carboxamide and their analgesic properties
Authors: Ukrainets, I. V.
Shishkina, S. V.
Baumer, V. N.
Gorokhova, O. V.
Petrushova, L. A.
Sim, G.
Украинец, И. В.
Шишкина, С. В.
Баумер, В. Н.
Горохова, О. В.
Петрушова, Л. А.
Сим, Г.
Українець, І. В.
Шишкіна, С. В.
Баумер, В. Н.
Горохова, О. В.
Петрушова, Л. О.
Сім, Г.
Keywords: pharmaceutical compound;pharmacological study;crystal structure;2 6,1-benzothiazine3-carboxamide;antinociceptive activity;chiral crystals;analgesic activity;фармацевтична композиція;Фармакологічне дослідження;кристалічна структура; ; .;2,6,1-бензотіазин-3-карбоксамід;антиноцицептивна активність;хіральні кристали;анальгетична активність;фармацевтическое соединение;фармакологическое исследование;кристалическая структура;хиральные кристаллы;антиноцицептивная активность;анальгетическая активность
Issue Date: 2016
Publisher: IUCr Journals
Bibliographic description (Ukraine): Ukrainets, I. V. Two pseudo-enantiomeric forms of N -benzyl-4-hydroxy-1 methyl-2,2-dioxo-1 H -2λ6,1-benzothiazine-3-carboxamide and their analgesic properties / I. V. Ukrainets, S. V. Shishkina, V. N. Baumer et. al. // Acta crystallographica. Section C. - 2016. - C72. - P. 411-417.
Abstract: The fact that molecular crystals exist as different polymorphic modifications and the identification of as many polymorphs as possible are important considerations for the pharmaceutic industry. The molecule of N-benzyl-4hydroxy-1-methyl-2,2-dioxo-1H-2 6,1-benzothiazine-3-carboxamide, C17H16N2O4S, does not contain a stereogenic atom, but intramolecular hydrogen-bonding interactions engender enantiomeric chiral conformations as a labile racemic mixture. The title compound crystallized in a solvent-dependent single chiral conformation within one of two conformationally polymorphic P212121 orthorhombic chiral crystals (denoted forms A and B). Each of these pseudoenantiomorphic crystals contains one of two pseudo-enantiomeric diastereomers. Form A was obtained from methylene chloride and form B can be crystallized from N,N-dimethylformamide, ethanol, ethyl acetate or xylene. Pharmacological studies with solid–particulate suspensions have shown that crystalline form A exhibits an almost fourfold higher antinociceptive activity compared to form B.
Description: DOI: 10.1107/S2053229616005453
Appears in Collections:Наукові публікації кафедри фармацевтичної хімії

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