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Issue 16, 2014
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A modular lead-oriented synthesis of diverse piperazine, 1,4-diazepane and 1,5-diazocane scaffolds

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Abstract

Piperazines are found widely in commercially-available compounds and bioactive molecules (including many drugs). However, in the vast majority of these molecules, the piperazine ring is isolated (i.e. not fused to another ring) and is not substituted on any of its carbon atoms. A modular synthetic approach is described in which combinations of cyclic sulfamidate and hydroxy sulfonamide building blocks may be converted into piperazines and related 1,4-diazepine and 1,5-diazocane scaffolds. By variation of the combinations of building blocks used, it was possible to vary the ring size, substitution and configuration of the resulting heterocyclic scaffolds. The approach was exemplified in the synthesis of a range of heterocyclic scaffolds that, on decoration, would target lead-like chemical space. It was demonstrated that lead-like small molecules based on these scaffolds would likely complement those found in large compound collections.

Graphical abstract: A modular lead-oriented synthesis of diverse piperazine, 1,4-diazepane and 1,5-diazocane scaffolds

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Publication details

The article was received on 16 Dec 2013, accepted on 27 Feb 2014 and first published on 10 Mar 2014


Article type: Paper
DOI: 10.1039/C3OB42512F
Author version available: Download Author version (PDF)
Citation: Org. Biomol. Chem., 2014,12, 2584-2591
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    A modular lead-oriented synthesis of diverse piperazine, 1,4-diazepane and 1,5-diazocane scaffolds

    T. James, P. MacLellan, G. M. Burslem, I. Simpson, J. A. Grant, S. Warriner, V. Sridharan and A. Nelson, Org. Biomol. Chem., 2014, 12, 2584
    DOI: 10.1039/C3OB42512F

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