Rapid synthesis and zebrafish evaluation of a phenanthridine-based small molecule library

Lauren R. Donaldson; Stephen Wallace; David Haigh; E. Elizabeth Patton; Alison N. Hulme

doi:10.1039/C0OB00449A

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Organic & Biomolecular Chemistry

Issue 7, 2011

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Rapid synthesis and zebrafish evaluation of a phenanthridine-based small molecule library

Lauren R. Donaldson , Stephen Wallace , David Haigh , E. Elizabeth Patton and Alison N. Hulme

Org. Biomol. Chem., 2011,9, 2233-2239

DOI: 10.1039/C0OB00449A
Received 19 Jul 2010, Accepted 20 Dec 2010
First published on the web 21 Dec 2010
This article is part of the collection: Chemical Biology

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A Heck cyclisation approach is described for the rapid synthesis of a library of natural product-like small molecules, based on the phenanthridine core. The synthesis of a range of substituted benzylamine building blocks and their incorporation into the library is reported, together with a highly selective cis-dihydroxylation protocol that enables access to the target compounds in an efficient manner. Biological evaluation of the library using zebrafish phenotyping has led to the discovery of compound 20c, a novel inhibitor of early-stage zebrafish embryo development.