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

✍ Scribed by Mlochowski, Jacek ;Juchniewicz, Leszek ;Kloc, Krystian ;Gryglewski, Ryszard J. ;Jakubowski, Andrzej ;Inglot, Anna D.

• Publisher: John Wiley and Sons
• Year: 1996
• Tongue: English
• Weight: 607 KB
• Volume: 1996
• Category: Article
• ISSN: 0947-3440
• DOI: 10.1002/jlac.199619961108

✦ Synopsis

Abstract

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).