A combinatorial access to 1,5-benzodiazepine derivatives and their evaluation for aldose reductase inhibition

被引：17

作者：

Pozarentzi, Minodora ^{[1
]}

Stephanidou-Stephanatou, Julia ^{[1
]}

Tsoleridis, Constantinos A. ^{[1
]}

Zika, Chariklia ^{[2
]}

Demopoulos, Vassilis ^{[2
]}

机构：

[1] Aristotle Univ Thessaloniki, Dept Chem, Organ Chem Lab, Thessaloniki 54124, Macedonia, Greece

[2] Aristotle Univ Thessaloniki, Sch Pharm, Dept Pharmaceut Chem, Thessaloniki 54124, Macedonia, Greece

来源：

TETRAHEDRON | 2009年 / 65卷 / 36期

关键词：

Aldose reductase inhibitors; Aryldiazepinothiophenones; Benzodiazepines; o-Phenylenediamines; Mercaptopropionic acid; Multicomponent reaction; Thiazolo[3,4-a][1,3]benzimidazoles; ONE-POT SYNTHESIS; SOLVENT-FREE CONDITIONS; CYCLOADDITION; ACID; 1H,3H-THIAZOLO<3,4-A>BENZIMIDAZOLES; 1,5-BENZOTHIAZEPINES; BENZOHETEROAZEPINE; RECEPTOR; AGENTS; CNS;

D O I：

10.1016/j.tet.2009.06.080

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

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 H-1 and C-13 NMR signals were based on the analysis of their H-1 and C-13 NMR (1 D and 2D), IR, MS and elemental analysis data. Compounds 4 were evaluated for aldose reductase inhibition and also as antioxidants. (C) 2009 Elsevier Ltd. All rights reserved.

引用

页码：7741 / 7751

页数：11

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