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
收藏
页码：7741 / 7751
页数：11
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