Search

β-Seleno amines were screened for in vitro antioxidant activity. The compounds (C1-C4) were tested against lipid peroxidation induced by iron and sodium nitroprusside in rat brain and liver homogenates. The compounds showed inhibition against thiobarbituric acid reactive species (TBARS) induced by different pro-oxidants (10μM FeSO(4) and 5μM sodium nitroprusside (SNP) in rat brain and liver homogenates. The compounds exhibited strong antioxidant activity in 2,2-diphenyl-1-picrylhydrazyl (DPPH) radical and phosphomolybdenum assays. The IC(50) values revealed that the β-seleno amines in which the amino group was protected with protecting groups tert-butyloxycarbonyl (Boc) and Tosyl (Ts) groups showed better antioxidant profiles compared to the free monoselenides. The total antioxidant activity of C1, C2, C3 and C4 were found to be 85.2±11.5, 114±7.9, 138±8.5, 125.81±5.2μM/ml of ascorbic acid respectively. Therefore, these compounds may be used as synthetic antioxidants., (Copyright © 2012 Elsevier B.V. All rights reserved.)

A highly efficient protocol is reported for the synthesis of chiral β-seleno amines via the ring-opening reaction of aziridines. Under neutral conditions, employing a stable phenyl selenolate specie (PhSeZnBr) and (BMIM)BF4 as solvent, β-seleno amines were obtained in good to excellent yields. Reuse of the ionic liquid was also possible, and four runs were performed with no decrease in the yields. [ABSTRACT FROM AUTHOR]