Selective synthesis and comparative activity of olefinic isomers of 1,2-benzothiazine-1,1-dioxide carboxylates as aldose reductase inhibitors

Crystal structure of 2-(4-methylphenyl)-4H-1,3-benzothiazine

“…For the biological importance of benzothiazine derivatives, see: Ahmad et al (2010); Gupta et al (2002); Lazzeri et al (2001); Parveen et al (2014); Zia-ur-Rehman et al (2006 Table 1 Hydrogen-bond geometry (Å , ).…”

“…Also, benzothiazine derivatives have shown activities for the treatment of asthmatic therapy (Lazzeri et al, 2001). Recently, 1,2-benzothiazine-1,1dioxide and its derivatives were reported as aldose reductase inhibitors (Parveen et al, 2014). With this potential background of benzothiazine derivatives, we have synthesized the title compound to study its crystal structure.…”

2-[(Z)-1,1-Dioxo-2-(2,4,5-trifluorobenzyl)-3,4-dihydro-2H-1,2-benzothiazin-4-ylidene]acetic acid

“…For pharmaceuticals properties of 1,2-benzothiazines, see: Lombardino et al (1971); Turck et al (1996); Zia-ur-Rehman et al (2005). For the biological properties and synthetic details of the title compound, see: Parveen et al (2014). For related structures, see: Ahmad et al (2008); Zia-ur-Rehman et al (2008); Yang et al (2012).…”

2-[(E)-1,1-Dioxo-2-(2,4,5-trifluorobenzyl)-3,4-dihydro-2H-1,2-benzothiazin-4-ylidene]acetic acid

“…For pharmaceutical and biological properties of 1,2-benzothiazines, see: Zia-ur-Rehman et al (2005); Lombardino et al (1971); Bihovsky et al (2004); For synthetic details of the title compound, see: Parveen et al (2014b). For related structures, see: Yang et al (2012); Parveen et al (2014a).…”

“…1,2-Benzothiazine-1,1-dioxide derivatives are reported as having anti-inflammatory and anti-bacterial activities (Lombardino et al, 1971) while some of its derivatives have been found to be calpain 1 inhibitors (Bihovsky et al, 2004). More recently, its derivatives were reported as aldose reductase inhibitors (Parveen et al, 2014b). Herein, we report the structure of the title derivative, C 17 H 12 F 3 NO 4 S, which is the E isomer of the previously published isomer 2-[(Z)-1,1-dioxo-2-(2,4,5-trifluorobenzyl)-3,4-dihydro-2H-1,2-benzothiazin-4-ylidene]acetic acid (Parveen et al, 2014a).…”