Synthesis and Antiproliferative Activity of Steroidal Diaryl Ethers

Novel 13α-estrone derivatives have been synthesized via direct arylation of the phenolic hydroxy function. Chan–Lam couplings of arylboronic acids with 13α-estrone as a nucleophilic partner were carried out under copper catalysis. The antiproliferative activities of the newly synthesized diaryl ethe...

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Bibliographic Details
Main Authors: Kovács Édua
Ali Hazhmat
Minorics Renáta
Traj Péter
Resch Vivien Erzsébet
Paragi Gábor
Bruszel Bella
Zupkó István
Mernyák Erzsébet
Format: Article
Published: 2023
Series:MOLECULES 28 No. 3
Subjects:
doi:10.3390/molecules28031196

mtmt:33594496
Online Access:http://publicatio.bibl.u-szeged.hu/28366
Description
Summary:Novel 13α-estrone derivatives have been synthesized via direct arylation of the phenolic hydroxy function. Chan–Lam couplings of arylboronic acids with 13α-estrone as a nucleophilic partner were carried out under copper catalysis. The antiproliferative activities of the newly synthesized diaryl ethers against a panel of human cancer cell lines (A2780, MCF-7, MDA-MB 231, HeLa, SiHa) were investigated by means of MTT assays. The quinoline derivative displayed substantial antiproliferative activity against MCF-7 and HeLa cell lines with low micromolar IC50 values. Disturbance of tubulin polymerization has been confirmed by microplate-based photometric assay. Computational calculations reveal significant interactions of the quinoline derivative with the taxoid binding site of tubulin.
Physical Description:17
ISSN:1420-3049