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. Issue 1 (10th December 2019)

• Record Type: Journal Article
• Authors: Shishkina, Svitlana V.; Ukrainets, Igor V.; Vashchenko, Olga V.; Voloshchuk, Natali I.; Bondarenko, Pavlo S.; Petrushova, Lidiya A.; Sim, Galina
• Is Part Of: Acta crystallographica. Volume 76:Issue 1(2020)
• Page Start: 69
• Page End: 74
• Publication Date: 2019-12-10
• Subjects: enantiomorph -- crystal structure -- benzothiazine‐3‐carboxamide -- piroxicam analogue; Crystallography -- Periodicals; Crystals -- Periodicals; 548.3
• DOI: 10.1107/S2053229619016450
• Languages: English
• ISSNs: 2053-2296

Abstract

Abstract : Two enantiomorphic crystal forms of N ‐(2, 6‐dimethylphenyl)‐4‐hydroxy‐2, 2‐dioxo‐1 H ‐2λ 6, 1‐benzothiazine‐3‐carboxamide have been crystallized from different solvents. A pharmacological study showed that one possesses a high analgesic activity, while the other revealed a strong anti‐inflammatory activity. The ability to become a stereogenic centre due to the non‐equivalence of its O atoms in hydrogen‐bond formation is a property of the ring sulfonyl group. Abstract : The title benzothiazine‐3‐carboxamide, C17 H16 N2 O4 S, crystallized in two enantiomorphic crystal forms with the space groups P 32 and P 31 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.