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Synthesis and Properties of 2‐Carboxyalkyl‐1,2‐benzisoselenazol‐3(2 H )‐ones and Related Organoselenium Compounds as Nitric Oxide Synthase Inhibitors and Cytokine Inducers
Author(s) -
Mlochowski Jacek,
Juchniewicz Leszek,
Kloc Krystian,
Gryglewski Ryszard J.,
Jakubowski Andrzej,
Inglot Anna D.
Publication year - 1996
Publication title -
liebigs annalen
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 0947-3440
DOI - 10.1002/jlac.199619961108
Subject(s) - chemistry , nitric oxide , nitric oxide synthase , diselenide , cytokine , inducer , medicinal chemistry , chloride , stereochemistry , biochemistry , organic chemistry , immunology , selenium , gene , biology
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).