Facile synthesis of 2,2′-dichalcogenobis (N-alkyl/aryl benzenesulfonamides) from N-substituted benzenesulfonamides and the emergence of 2-alkyl 1,3,2-benzothiaselenazole 1,1 dioxides. Ebselen analogues
✍ Scribed by Sungano Mhizha
- Publisher
- Elsevier Science
- Year
- 1997
- Tongue
- French
- Weight
- 584 KB
- Volume
- 53
- Category
- Article
- ISSN
- 0040-4020
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✦ Synopsis
Absfmct: A one pot synthesis of 2-2'-diselenobis/ditellurobis(N-alkyl/aryl benzenesulfonamides) 4a-h from N-alkyl/aryl benzenesulfonamides is elaborated. The first cyclization of 2-2' -diselenobis (N-methyl benzenesulfonamide)
4a into 2-methyl-1,3,2+enzothiaselenazole 1.1 dioxide (5a)" using 3chloroperoxybenzoic acid is described. Compounds 4a-h and 5a and d act as a new class of biologically activelb compounds. 0 1997 Elsevier Science Ltd. Many clinical pathological conditions are accompanied or even caused by oxidative stress which is characterised by a situation that more reactive oxygen species are formed than can be counteracted by the antioxidant defense system of the organism.* Inflammatory conditions linked to lipid peroxidation and its products, formed either enzymatically or by auto-oxidation include certain carcinomas, rheumatoid arthritis, bums, shock, post ischaemic necrosis, psoriasis and asthma, Parkinson's disease, epilepsy and neuronal ceroid lipofuscinosis, liver cirrhosis and radiation damage.3 In these conditions and other diseases such as myocardial infarction and atherosclerosis, chronic renal failure, phenyl ketonurea, muscular dystrophy, sudden child death, cystic fibrosis, cataracts, diabetes, Down's syndrome, Keshan's disease, Kwashiorkor, congestive heart failure in children and young women, growth and mental retardation, depleted selenium levels and/or low glutathione peroxidase activities in humans have been observed.4 In a number of the above cases selenium supplementation was claimed to improve the condition.314 Some seleno-organic compounds have also been found to be. antiviral,' antimalarial6 and cytokine inducers where the reference compound has been preferentially ebselen.5,7CJ Interferons (a, p and $ are known to inhibit many different RNA and DNA viruses while tumor necrosis factors are known to be potent especially during tumor growth, bacterial and parasitic infections.
Earlier findings confirmed that the elements oxygen, sulfur, selenium and probably tellurium have immunomodulatory activities." It would therefore be rational to look for these element combinations to redress the above mentioned epidemics and such projections are at the heart of this synthetic work.
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