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

*Corresponding author for this work

Research output: Contribution to journalArticlepeer-review

15 Scopus citations

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.

Original languageEnglish
Pages (from-to)1684-1690
Number of pages7
JournalChemistry - An Asian Journal
Volume7
Issue number7
DOIs
StatePublished - 1 Jun 2012

Keywords

  • Pictet-Spengler-type reactions
  • drug discovery
  • heterocycles
  • privileged structures
  • synthesis design

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