Structure of Chlormezanone

Crystal structures of rac-2,3-diphenyl-2,3,5,6-tetrahydro-4H-1,3-thiazine-1,1,4-trione and N-[(2S,5R)-1,1,4-trioxo-2,3-diphenyl-1,3-thiazinan-5-yl]acetamide

“…The 2,3-dihydro-4H-1,3-thiazin-4-ones are a group of sixmembered heterocycles with a wide range of biological activity (Ryabukhin et al, 1996;Silverberg & Moyer, 2019). Surrey's research (Surrey et al, 1958;Surrey, 1963a,b) resulted in the discovery of two drugs, the antianxiety and muscle relaxant chlormezanone, C 11 H 12 ClNO 3 S, [2-(4-chlorophenyl)-3-methyl-2,3,5,6-tetrahydro-4H-1,3-thiazin-4-one 1,1-dioxide] (O 'Neil, 2006;Tanaka & Horayama, 2005) and the muscle relaxant dichlormezanone, C 11 H 11 Cl 2 NO 3 S, [2-(3,4-dichlorophenyl)-3-methyl-2,3,5,6-tetrahydro-4H-1,3-thiazin-4-one 1,1dioxide] (Elks & Ganellin, 1990). These sulfones showed greater activity than the sulfides from which they were synthesized (Surrey et al, 1958).…”

Crystal structure of (1S,2S,5R)-5-acetylamino-4-oxo-2,3-diphenyl-1,3-thiazinan-1-ium-1-olate

“…The 1,3-thiazin-4-ones are a group of six-membered heterocycles with a wide range of biological activity (Ryabukhin et al, 1996). Surrey's research (Surrey et al, 1958;Surrey, 1963a,b) resulted in the discovery of two drugs, the antianxiety and muscle relaxant chlormezanone [2-(4-chlorophenyl)-3-methyl-2,3,5,6-tetrahydro-4H-1,3-thiazin-4-one 1,1dioxide] (O'Neil, 2006;Tanaka & Horayama, 2005) and muscle relaxant dichloromezanone [2-(3,4-dichlorophenyl)-3methyl-2,3,5,6-tetrahydro-4H-1,3-thiazin-4-one 1,1-dioxide] (Elks & Ganellin, 1990). These sulfones showed greater activity than the sulfides from which they were synthesized (Surrey et al, 1958).…”

“…Crystal structures of a number of 1,3-thiazolidin-4-one 1-oxides have been reported (Wang et al, 2010;Johnson et al, 1983;Chen et al, 2011;Colombo et al, 2008;Yennawar, Hullihen et al, 2015) and the structure of chlormezanone [2-(4-chlorophenyl)-3-methyl-2,3,5,6-tetrahydro-4H-1,3-thiazin-4-one 1,1-dioxide] has also been reported (Tanaka & Horayama, 2005). We have reported previously the crystal structure of 2,3-diphenyl-2,3,5,6-tetrahydro-4H-1,3-thiazin-4one 1-oxide (Yennawar et al, 2016).…”

Crystal structure of rac-2,3-diphenyl-2,3,5,6-tetrahydro-4H-1,3-thiazin-4-one 1-oxide

“…Crystal structures of a number of 1,3-thiazolidin-4-one 1-oxides have been reported (Wang et al, 2010;Johnson et al, 1983;Chen et al, 2011;Colombo et al, 2008;Yennawar et al, 2015); in each case the oxygen on sulfur and the group on C-2 had a trans relationship, as does the structure reported here. The structure of chlormezanone [2-(4-chlorophenyl)-3methyl-2,3,5,6-tetrahydro-4H-1,3-thiazin-4-one 1,1-dioxide] has also been disclosed (Tanaka & Horayama, 2005). To the best of our knowledge, there have been no published crystal structures of a 2,3,5,6-tetrahydro-4H-1,3-thiazin-4-one 1-oxide.…”