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Issue 37, 2012
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A two-directional strategy for the diversity-oriented synthesis of macrocyclic scaffolds

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Abstract

Macrocyclic compounds represent a structural class with exceptional potential for biological activity; however, they have historically been underrepresented in screening collections and synthetic libraries. In this article we report the development of a highly step-efficient strategy for the diversity-oriented synthesis of complex macrocyclic architectures, using a modular approach based on the two-directional synthesis of bifunctional linear precursors and their subsequent combination in a two-directional macrocyclisation process. In this proof of principle study, the synthesis of 14 such compounds was achieved. Cheminformatic analysis of the compounds produced suggests that they reside in biologically relevant regions of chemical space and the compounds were screened for activity against two cancer cell lines.

Graphical abstract: A two-directional strategy for the diversity-oriented synthesis of macrocyclic scaffolds

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Publication details

The article was received on 04 Jul 2012, accepted on 03 Aug 2012, published on 03 Aug 2012 and first published online on 03 Aug 2012


Article type: Paper
DOI: 10.1039/C2OB26272J
Citation: Org. Biomol. Chem., 2012,10, 7545-7551
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    A two-directional strategy for the diversity-oriented synthesis of macrocyclic scaffolds

    K. M. G. O'Connell, H. S. G. Beckmann, L. Laraia, H. T. Horsley, A. Bender, A. R. Venkitaraman and D. R. Spring, Org. Biomol. Chem., 2012, 10, 7545
    DOI: 10.1039/C2OB26272J

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