Synthesis and properties of 2-carboxyalkyl-1,2-benzisoselenazol-3(2H)-ones and related organoselenium compounds as nitric oxide synthase inhibitors and cytokine inducers

Article abstract of DOI:10.1002/jlac.199619961108

A convenient synthesis of the 2-carboxyalkyl-1,2-benzisoselenazol-3(2H)-ones 4a-k and their esters 41-p from 2-(chloroseleno)benzoyl chloride (2) and amino acids or their carboxy esters is reported. In similar way other 2-substituted 1,2-benzisoselenazol-3(2H)-ones 4q-u were synthesized. The related bis[2-(carbamoyl)phenyl] diselenides 5 were obtained by reductive conversion of 1,2-benzisoselenazol-3(2H)-ones 4 or directly by the reaction of bis[2-(chlorocarbonyl)phenyl] diselenide (3) with compounds having a primary amino group. It was found that some of compounds 4 and 5 are modest cytokine (TNF, IFN) inducers in human peripheral blood leucocyte cultures and block the constitutive endothelial nitric oxide synthase (ce NOS). VCH Verlagsgesellschaft mbH, 1996.