Design and Synthesis of New Biprivileged Molecular Scaffolds: Indolo‐Fused Benzodiazepinyl/quinoxalinyl benzimidazoles |
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| Authors: | Indrajeet J Barve Chan‐Yu Chen Deepak B Salunke Prof Wen‐Sheng Chung Prof Chung‐Ming Sun |
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| Institution: | Department of Applied Chemistry, National Chiao Tung University, Hsinchu 300 (Taiwan) |
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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. |
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| Keywords: | drug discovery heterocycles Pictet– Spengler‐type reactions privileged structures synthesis design |
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