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

被引：3

作者：

Shishkina, Svitlana, V ^{[1
,2
]}

Ukrainets, Igor, V ^{[3
]}

Vashchenko, Olga V. ^{[4
]}

Voloshchuk, Natali, I ^{[5
]}

Bondarenko, Pavlo S. ^{[5
]}

Petrushova, Lidiya A. ^{[3
]}

Sim, Galina ^{[6
]}

机构：

[1] NAS Ukraine, SSI Inst Single Crystals, 60 Nauky Ave, UA-61001 Kharkov, Ukraine

[2] Kharkov Natl Univ, Dept Inorgan Chem, 4 Svobody Sq, UA-61077 Kharkov, Ukraine

[3] Natl Univ Pharm, Dept Pharmaceut Chem, 53 Pushkinska St, UA-61002 Kharkov, Ukraine

[4] NAS Ukraine, Inst Scintillat Mat, 60 Nauky Ave, UA-61001 Kharkov, Ukraine

[5] NI Pirogov Vinnitsa Natl Med Univ, Dept Pharmacol, 56 Pirogov St, UA-21018 Vinnitsa, Ukraine

[6] Far Eastern State Med Univ, Dept Pharmaceut Chem, 35 Muravev Amursky St, Khabarovsk 680000, Russia

来源：

ACTA CRYSTALLOGRAPHICA SECTION C-STRUCTURAL CHEMISTRY | 2020年 / 76卷 / 76期

关键词：

enantiomorph; crystal structure; benzothiazine-3-carboxamide; piroxicam analogue; CRYSTAL-STRUCTURES; POLYMORPHISM;

D O I：

10.1107/S2053229619016450

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

The title benzothiazine-3-carboxamide, C17H16N2O4S, crystallized in two enantiomorphic crystal forms with the space groups P3(2) and P3(1) 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.

引用

页码：69 / +

页数：16

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