Ethyl 2-{(2Z)-2-[(1-naphthylsulfonyl)imino]-2,3-dihydro-1,3-thiazol-4-yl}acetate monohydrate

The title compound, C17H16N2O4S2·H2O, is of interest with respect to its antidiabetic and anti-obesity activity. In the crystal, the packing is stabilized by three cooperative interactions: offset π–π interactions [centroid–centroid distance = 3.604 (2) Å], as well as C—H⋯O and O—H⋯O hydrogen bonds. N—H⋯O interactions also occur.

The title compound, C 17 H 16 N 2 O 4 S 2 ÁH 2 O, is of interest with respect to its antidiabetic and anti-obesity activity. In the crystal, the packing is stabilized by three cooperative interactions: offsetinteractions [centroid-centroid distance = 3.604 (2) Å ], as well as C-HÁ Á ÁO and O-HÁ Á ÁO hydrogen bonds. N-HÁ Á ÁO interactions also occur.

Comment
The biochemistry and pharmacology of sulfur containing compounds are a subject of intense current interest, especially from the point of view of public health. Obesity and diabetes are major causes of morbidity and mortality in many countries (Saiah, 2008). Excessive levels of glucocorticoids into the body can cause both metabolic complications. The regulation of glucocorticoid production involves two 11b-hydroxysteroid dehydrogenase (11b-HSD) isozymes, that interconvert cortisone and cortisol. 11b-HSD1 is a reductase that amplifies glucocorticoid action in a tissue-specific manner (Fotsch et al., 2008).
Recent studies suggest that inhibition of 11b-HSD1 increases hepatic insulin sensivity along with decreased glucose production . Selective inhibitors of 11b-HSD1 have considerable potential as treatments of type 2 diabetes and obesity (Vicker et al., 2007). BVT 14225 is a new selective 11b-HSD1 inhibitor, it belongs to a class of arylsulfonamidothiazoles with in vitro and in vivo antidiabetic effects (Barf et al., 2002).
In order to assist our knowledge about the electronic and steric requirements in arylsulfonamidothiazoles that show antidiabetic and antiobesity activities (Navarrete-Vázquez et al., 2008), we have synthesized and determined the crystal structure of the title compound (I), which is a precursor in the synthesis of an amide BVT14225 bioisoster.
Single crystals of (I) were obtained from ethanol.  Fig. 1. The molecular structure of (I) showing the atom-labelling scheme. Displacement ellipsoids are drawn at the 50% probability level and H atoms are shown as small spheres of arbitrary radius.