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.
ASJC Scopus subject areas
- Physical and Theoretical Chemistry
- Organic Chemistry
Donaldson, L. R., Wallace, S., Haigh, D., Patton, E. E., & Hulme, A. N. (2011). Rapid synthesis and zebrafish evaluation of a phenanthridine-based small molecule library. Organic and Biomolecular Chemistry, 9(7), 2233-2239. https://doi.org/10.1039/c0ob00449a