Synthesis, Characterization, and X-Ray Structures of 2-(3,5<i>-</i>Dimethylpyrazol-1-Yl)Phenyl-Based Organoselenium Compounds and Their Glutathione Peroxidase (Gp<i>x</i>) Like Activity
作者:Ananda S. Hodage、Prasad P. Phadnis、Amey Wadawale、K. I. Priyadarsini、Vimal K. Jain
DOI:10.1080/10426507.2012.686545
日期:2012.12.1
The synthesis of a series of 2-(3,5-dimethylpyrazol-1-yl)phenyl-based organose-lenium compounds, (dmpzC(6)H(4)Se)(2) (1), dmpzC(6)H(4)SeR (dmpz = 3,5-dimethylpyrazol-1-yl; R = (CH2)(n)Y; Y = OH, NH2, and COOH), and dmpzC(6)H(4)SeX (X = Cl, Br, or I) is described. The compounds are characterized by IR, NMR (H-1, C-13H-1}, Se-77H-1}), and mass spectral (MS) data. The molecular structures of (dmpzC(6)H(4)Se)(2), dmpzC(6)H(4)SeCH(2)COOH, and dmpzC(6)H(4)SeCH(2)CH(2)OH have been established by X-ray crystallography. The two latter compounds are associated in the solid state through intermolecular hydrogen bonding between the OH proton and the pyrazolyl nitrogen atom of the adjacent molecule. Glutathione peroxidase (GPx) like catalytic activity of these compounds has been evaluated by using hydrogen peroxide (H2O2) as substrate and dithiothreitol (DTTred) as thiol cofactor in CD3OD, and the progress of the reaction was monitored by H-1 NMR spectroscopy. All the compounds exhibited the GPx-like catalytic activity. Among these, the ones containing alkylamino groups showed the best activity.