Synthesis and Properties of 2‐Carboxyalkyl‐1,2‐benzisoselenazol‐3(2H)‐ones and Related Organoselenium Compounds as Nitric Oxide Synthase Inhibitors and Cytokine Inducers

A convenient synthesis of the 2‐carboxyalkyl‐1,2‐benzisoselenazol‐3(2 H )‐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(2 H )‐ones 4q–u were synthesized. The related bis[2‐(carbamoyl)phenyl] diselenides 5 were obtained by reductive conversion of 1,2‐benzisoselenazol‐3(2 H )‐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).