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(2H )-ones 4a-k and their esters 41-p from 2-(chloroseleno)benzoyl chlorid e (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 synt hesized. The related bis[2-(carbomoyl)phenyl] diselenides 5 were obtai ned by reductive conversion of 1,2-benzisoselenazol-3(2H)-ones 4 or di rectly by the reaction of bis[2-(chlorocarbonyl)phenyl] diselenide (3) with compounds having a primary amino group. It was found the some of compounds 4 and 5 are modest cytokine (TNF, IFN) inducers in human pe ripheral blood leucocyte culture and block the constitutive endothelia l nitric oxide synthase (ce NOS).