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Biological properties of two enantiomorphic forms of N-(2,6-dimethylphenyl)-4-hydroxy-2,2-dioxo-1H-2λ6,1-benzothiazine-3-carboxamide, a structural analogue of piroxicam.
Acta Crystallographica Section C ( IF 0.8 ) Pub Date : 2020-01-01 , DOI: 10.1107/s2053229619016450
Svitlana V Shishkina 1 , Igor V Ukrainets 2 , Olga V Vashchenko 3 , Natali I Voloshchuk 4 , Pavlo S Bondarenko 4 , Lidiya A Petrushova 2 , Galina Sim 5
Affiliation  

The title benzothiazine-3-carboxamide, C17H16N2O4S, crystallized in two enantiomorphic crystal forms with the space groups P32 and P31 despite 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.

中文翻译:

N-(2,6-二甲基苯基)-4-羟基-2,2-二氧代-1H-2λ6,1-苯并噻嗪-3-羧酰胺(吡罗昔康的结构类似物)的两种对映体形式的生物学特性。

标题苯并噻嗪-3-羧酰胺C17H16N2O4S结晶为两种对映体晶型,空间群为P32和P31,尽管没有经典的立体原子。分子结构是彼此的镜像。仅有一个磺酰基O原子作为质子受体参与分子内氢键,并且该原子在两个对映体结构上不同。结果,S原子成为假立体中心。由于对映体形式的生物活性不同,这一事实值得考虑。一种形式具有较高的镇痛活性,而另一种形式具有较高的抗炎活性。
更新日期:2020-01-01
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