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Synthesis and Antiproliferative Activity of Steroidal Diaryl Ethers.

ABSTRACT: 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.

SUBMITTER: Kovacs E

PROVIDER: S-EPMC9919549 | biostudies-literature | 2023 Jan

REPOSITORIES: biostudies-literature

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Synthesis and Antiproliferative Activity of Steroidal Diaryl Ethers.

Kovács Édua É Ali Hazhmat H Minorics Renáta R Traj Péter P Resch Vivien V Paragi Gábor G Bruszel Bella B Zupkó István I Mernyák Erzsébet E

Molecules (Basel, Switzerland) 20230125 3

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 ...[more]

PMID: 36770863

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