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Issue 3, 2013
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3-Substituted 2-phenyl-indoles: privileged structures for medicinal chemistry

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Abstract

Privileged structures have been used in drug discovery targeting G protein-coupled receptors (GPCR) and other protein classes for more than 20 years. Their rich activity profiles and drug-like characteristics lend themselves to increased productivity in hit identification and lead optimisation. Recently we discovered two allosteric modulators 1 and 2 for the G protein-coupled receptor GPRC6A incorporating the privileged 2-phenyl-indole scaffold, functionalised at the 3-position. In order to develop new potential GPRC6A ligands we engaged in the development of synthetic routes to provide 2-phenyl-indoles with a variety of substituents at the indole 3-position. Herein we describe the development of optimised and efficient synthetic routes to a series of new 2-phenyl-indole building blocks 3 to 9 and show that these can be used to generate a broad variety of 3-substituted 2-phenyl-indoles of interest to medicinal chemists.

Graphical abstract: 3-Substituted 2-phenyl-indoles: privileged structures for medicinal chemistry

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Publication details

The article was received on 22 Aug 2012, accepted on 01 Nov 2012 and first published on 01 Nov 2012


Article type: Paper
DOI: 10.1039/C2RA21902F
Citation: RSC Adv., 2013,3, 945-960
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    3-Substituted 2-phenyl-indoles: privileged structures for medicinal chemistry

    H. Johansson, T. B. Jørgensen, D. E. Gloriam, H. Bräuner-Osborne and D. S. Pedersen, RSC Adv., 2013, 3, 945
    DOI: 10.1039/C2RA21902F

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