Total synthesis and biological evaluation of simplified aplyronine analogues as synthetically tractable anticancer agents.
Pettigrew, Talia R
Porter, Rachel J
Housden, Michael P
Chemical communications (Cambridge, England)
Royal Society of Chemistry (RSC)
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Pettigrew, T. R., Porter, R. J., Walsh, S., Housden, M. P., Lam, N., Carroll, J., Parker, J. S., et al. (2020). Total synthesis and biological evaluation of simplified aplyronine analogues as synthetically tractable anticancer agents.. Chemical communications (Cambridge, England), 56 (10), 1529-1532. https://doi.org/10.1039/c9cc09050a
The aplyronines are a family of highly cytotoxic marine natural products with potential application in targeted cancer chemotherapy. To address the severe supply issue, function-oriented molecular editing of their macrolactone scaffold led to the design of a series of simplified aplyronine analogues. Enabled by a highly convergent aldol-based route, the total synthesis of four analogues was achieved, with a significant improvement in step economy versus previous compounds, and their cancer cell growth inhibition in the HeLa cell line was determined. The modular strategy presented offers a means for significantly shortening their chemical synthesis to facilitate the continued development of this promising class of anticancer agent.
Hela Cells, Humans, Macrolides, Antineoplastic Agents, Cell Proliferation, Molecular Conformation, Structure-Activity Relationship, Stereoisomerism
External DOI: https://doi.org/10.1039/c9cc09050a
This record's URL: https://www.repository.cam.ac.uk/handle/1810/300619
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