Diversity-oriented synthesis of angular bis-benzimidazole derivatives under microwave irradiation

Chih Hau Chen, Ming Hsien Chien, Min Liang Kuo, Cheng Ting Chou, Jin Ji Lai, Shu Fen Lin, Suman Thummanagoti, Chung Ming Sun

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16 Citations (Scopus)

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.

Original languageEnglish
Pages (from-to)1038-1046
Number of pages9
JournalJournal of Combinatorial Chemistry
Volume11
Issue number6
DOIs
Publication statusPublished - Nov 9 2009
Externally publishedYes

ASJC Scopus subject areas

  • Chemistry(all)

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  • Cite this

    Chen, C. H., Chien, M. H., Kuo, M. L., Chou, C. T., Lai, J. J., Lin, S. F., Thummanagoti, S., & Sun, C. M. (2009). Diversity-oriented synthesis of angular bis-benzimidazole derivatives under microwave irradiation. Journal of Combinatorial Chemistry, 11(6), 1038-1046. https://doi.org/10.1021/cc900084s