A combinatorial access to 1,5-benzodiazepine derivatives and their evaluation for aldose reductase inhibition |
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| Authors: | Minodora Pozarentzi Constantinos A Tsoleridis Chariklia Zika |
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| Institution: | a Department of Chemistry, Laboratory of Organic Chemistry, Aristotle University of Thessaloniki, Thessaloniki 54124, Macedonia, Greece
b Department of Pharmaceutical Chemistry, School of Pharmacy, Aristotle University of Thessaloniki, Thessaloniki 54124, Macedonia, Greece |
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| Abstract: | Aryldiazepinothiophenones 4 were prepared from the reaction of o-phenylenediamines with acetone in the presence of 2-mercaptocarboxylic acids along with thiazolobenzodiazepines 6, thiazolobenzimidazoles 7 and 1,5-benzodiazepines 5, which were obtained as by-products. The benzodiazepinothiophenones 4a-d and the benzodiazepines 5a-d were also isolated from the reaction of o-phenylenediamines 1a-c with phorone. Structural assignments of the new compounds as well as complete assignment of 1H and 13C NMR signals were based on the analysis of their 1H and 13C NMR (1D and 2D), IR, MS and elemental analysis data. Compounds 4 were evaluated for aldose reductase inhibition and also as antioxidants. |
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| Keywords: | Aldose reductase inhibitors Aryldiazepinothiophenones Benzodiazepines o-Phenylenediamines Mercaptopropionic acid Multicomponent reaction Thiazolo[3 4-a][1 3]benzimidazoles |
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