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Design and synthesis of novel bicalutamide and enzalutamide derivatives as antiproliferative agents for the treatment of prostate cancer

Bassetto, Marcella, Ferla, Salvatore ORCID:, Pertusati, Fabrizio ORCID:, Kandil, Sahar ORCID:, Westwell, Andrew ORCID:, Brancale, Andrea ORCID: and McGuigan, Christopher ORCID: 2016. Design and synthesis of novel bicalutamide and enzalutamide derivatives as antiproliferative agents for the treatment of prostate cancer. European Journal of Medicinal Chemistry 118 , pp. 230-243. 10.1016/j.ejmech.2016.04.052

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Prostate cancer (PC) is one of the major causes of male death worldwide and the development of new and more potent anti-PC compounds is a constant requirement. Among the current treatments, (R)-bicalutamide and enzalutamide are non-steroidal androgen receptor antagonist drugs approved also in the case of castration-resistant forms. Both these drugs present a moderate antiproliferative activity and their use is limited due to the development of resistant mutants of their biological target. Insertion of fluorinated and perfluorinated groups in biologically active compounds is a current trend in medicinal chemistry, applied to improve their efficacy and stability profiles. As a means to obtain such effects, different modifications with perfluoro groups were rationally designed on the bicalutamide and enzalutamide structures, leading to the synthesis of a series of new antiproliferative compounds. Several new analogues displayed improved in vitro activity towards four different prostate cancer cell lines, while maintaining full AR antagonism and therefore representing promising leads for further development. Furthermore, a series of molecular modelling studies were performed on the AR antagonist conformation, providing useful insights on potential protein-ligand interactions.

Item Type: Article
Date Type: Publication
Status: Published
Schools: Pharmacy
Additional Information: This work is dedicated to the memory of Prof. Chris McGuigan, a great colleague and scientist, invaluable source of inspiration and love for research. This is an open access article under the CCBY license.
Publisher: Elsevier
ISSN: 0223-5234
Date of First Compliant Deposit: 16 May 2016
Date of Acceptance: 21 April 2016
Last Modified: 06 Dec 2023 02:08

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