Design and synthesis of new biprivileged molecular scaffolds: indolo-fused benzodiazepinyl/quinoxalinyl benzimidazoles.

Indrajeet J Barve, Chan-Yu Chen, Deepak B Salunke, Wen-Sheng Chung, Chung-Ming Sun

Index: Chem. Asian J. 7(7) , 1684-90, (2012)

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Abstract

The present article describes the design and synthesis of new biprivileged molecular scaffolds with diverse structural features. Commercially available, simple heterocyclic building blocks such as 4-fluoro-3-nitrobenzoic acid, 2-chloro-3-nitrobenzoic acid, and indoline were utilized for the synthesis of the novel heterocycles. Pictet-Spengler-type condensation was used as a key step to construct tetracyclic indolo-benzodiazepines and indolo-quinoxalines linked with substituted benzimidazoles. Analysis of single crystals of representative compounds showed that these molecular skeletons have the potential to present various substituents with distinct three-dimensional orientations.Copyright © 2012 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.