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

研究成果: 雜誌貢獻文章

16 引文 (Scopus)

摘要

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.

原文英語
頁(從 - 到)1038-1046
頁數9
期刊Journal of Combinatorial Chemistry
11
發行號6
DOIs
出版狀態已發佈 - 十一月 9 2009
對外發佈Yes

指紋

3-nitrobenzoic acid
Microwave irradiation
Polymers
Vascular Endothelial Growth Factor Receptor-3
Benzimidazoles
Isothiocyanates
Derivatives
Cyclization
Aldehydes
Amides
Nuclear magnetic resonance spectroscopy
Amines
Protons
Screening
Substitution reactions
Cells
bis-benzimidazole
1,2-diaminobenzene
benzimidazole

ASJC Scopus subject areas

  • Chemistry(all)

引用此文

Diversity-oriented synthesis of angular bis-benzimidazole derivatives under microwave irradiation. / Chen, Chih Hau; Chien, Ming Hsien; Kuo, Min Liang; Chou, Cheng Ting; Lai, Jin Ji; Lin, Shu Fen; Thummanagoti, Suman; Sun, Chung Ming.

於: Journal of Combinatorial Chemistry, 卷 11, 編號 6, 09.11.2009, p. 1038-1046.

研究成果: 雜誌貢獻文章

Chen, CH, Chien, MH, Kuo, ML, Chou, CT, Lai, JJ, Lin, SF, Thummanagoti, S & Sun, CM 2009, 'Diversity-oriented synthesis of angular bis-benzimidazole derivatives under microwave irradiation', Journal of Combinatorial Chemistry, 卷 11, 編號 6, 頁 1038-1046. https://doi.org/10.1021/cc900084s
Chen, Chih Hau ; Chien, Ming Hsien ; Kuo, Min Liang ; Chou, Cheng Ting ; Lai, Jin Ji ; Lin, Shu Fen ; Thummanagoti, Suman ; Sun, Chung Ming. / Diversity-oriented synthesis of angular bis-benzimidazole derivatives under microwave irradiation. 於: Journal of Combinatorial Chemistry. 2009 ; 卷 11, 編號 6. 頁 1038-1046.
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