Biological properties of two enantiomorphic forms ofN-(2,6-dimethylphenyl)-4-hydroxy-2,2-dioxo-1H-2λ6,1-benzothiazine-3-carboxamide, a structural analogue of piroxicam-Reference-Cited by-同舟云学术

Biological properties of two enantiomorphic forms ofN-(2,6-dimethylphenyl)-4-hydroxy-2,2-dioxo-1H-2λ6,1-benzothiazine-3-carboxamide, a structural analogue of piroxicam

Published:2020-01-01 Issue:1 Volume:76 Page:69-74
ISSN:2053-2296
Container-title:Acta Crystallographica Section C Structural Chemistry
language:
Short-container-title:Acta Crystallogr C

Author:

Shishkina Svitlana V.^ORCID,Ukrainets Igor V.^ORCID,Vashchenko Olga V.,Voloshchuk Natali I.,Bondarenko Pavlo S.,Petrushova Lidiya A.,Sim Galina

Abstract

The title benzothiazine-3-carboxamide, C17H16N2O4S, crystallized in two enantiomorphic crystal forms with the space groupsP32andP31despite the absence of a classic stereogenic atom. The molecular structures are mirror images of each other. Only one sulfonyl O atom takes part in intramolecular hydrogen bonding as a proton acceptor and this atom is different in the two enantiomorphic structures. As a result, the S atom becomes a pseudo-stereogenic centre. This fact is worth taking into account due to the different biological activities of the enantiomorphic forms. One form possesses a high analgesic activity, while the other form revealed a high anti-inflammatory activity.

Publisher

International Union of Crystallography (IUCr)

Subject

Materials Chemistry,Inorganic Chemistry,Physical and Theoretical Chemistry,Condensed Matter Physics

Link

http://journals.iucr.org/c/issues/2020/01/00/ku3258/ku3258.pdf

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