Article

Divergent synthesis of unsymmetrical annulated biheterocyclic compound libraries: benzimidazole linked indolo-benzodiazepines/quinoxaline.

Laboratory of Combinatorial Drug Discovery, Department of Applied Chemistry National Chiao Tung University, Hsinchu, Taiwan.
ACS combinatorial science 06/2011; 13(4):391-8. DOI:10.1021/co200022u pp.391-8
Source: PubMed

ABSTRACT Diversity-oriented synthesis of novel benzimidazole linked indolo-benzodiazepine/quinoxaline ring systems using poly(ethylene glycol) as soluble polymer support is described. Commercially available 4-fluoro-3-nitrobenzoic acid and indoline were utilized for the construction of these annulated biheterocyclic compound libraries having multiple privileged structures with three-point structural diversity. A reagent based diversification approach coupled with the Pictet-Spengler-type condensation was used to construct the tetracyclic indolo-benzodiazepines/quinoxalines on substituted benzimidazoles.

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Keywords

annulated biheterocyclic compound libraries
 
benzimidazoles
 
Commercially available 4-fluoro-3-nitrobenzoic acid
 
Diversity-oriented synthesis
 
indolo-benzodiazepine/quinoxaline ring systems
 
poly(ethylene glycol)
 
soluble polymer support
 
three-point structural diversity
 

Li-Hsun Chen