Diversity-oriented synthesis of angular bis-benzimidazole derivatives under microwave irradiation
Journal
Journal of Combinatorial Chemistry
Journal Volume
11
Journal Issue
6
Pages
1038-1046
Date Issued
2009
Abstract
Pharmaceutically interesting, angular bis-benzimidazoles with three appendages have been synthesized successfully through a diversity-oriented approach with soluble support under microwave irradiation. Polymer immobilized o-phenylenediamine was selectively N-acylated with 2-chloro-3-nitrobenzoic acid in a primary aromatic amino moiety. The obtained amide was cyclized to benzimidazole in an acidic condition, and subsequently nucleophilic aromatic substitution with different amines was performed. Successive reduction, cyclization with various aldehydes and activated isothiocyanates yielded angular biheterocyclic benzimidazoles in good quantities. Reaction progress on polymer support was precisely monitored using the conventional proton NMR spectroscopy. Preliminary screening results showed some of these interesting compounds exhibited moderately to good inhibition against vascular endothelial growth factor receptor 3 (VEGFR-3), which is related to invasion and migration of cancer cells. ? 2009 American Chemical Society.
SDGs
Other Subjects
benzimidazole; benzimidazole derivative; article; chemical structure; chemistry; combinatorial chemistry; methodology; microwave radiation; stereoisomerism; synthesis; Benzimidazoles; Combinatorial Chemistry Techniques; Microwaves; Molecular Structure; Stereoisomerism
Type
journal article