Synthesis and Antiproliferative Activity of Steroidal Diaryl Ethers

被引：10

作者：

Kovacs, Edua ^{[1
]}

Ali, Hazhmat ^{[2
]}

Minorics, Renata ^{[2
]}

Traj, Peter ^{[1
]}

Resch, Vivien ^{[3
]}

Paragi, Gabor ^{[3
,4
,5
]}

Bruszel, Bella ^{[3
]}

Zupko, Istvan ^{[2
]}

Mernyak, Erzsebet ^{[1
]}

机构：

[1] Univ Szeged, Dept Organ Chem, H-6720 Szeged, Hungary

[2] Univ Szeged, Inst Pharmacodynam & Biopharm, H-6720 Szeged, Hungary

[3] Univ Szeged, Dept Med Chem, H-6720 Szeged, Hungary

[4] Univ Pecs, Inst Phys, H-7625 Pecs, Hungary

[5] Univ Szeged, Dept Theoret Phys, H-6720 Szeged, Hungary

来源：

MOLECULES | 2023年 / 28卷 / 03期

关键词：

Chan-Lam reaction; diaryl ether; 13; alpha-estrone; antiproliferative effect; tubulin polymerization; molecular dynamics; 13-ALPHA-ESTRONE DERIVATIVES; ANTICANCER AGENTS; BREAST-CANCER; IN-VITRO; INHIBITORS; DESIGN; DISCOVERY; GROWTH; COPPER; ACIDS;

D O I：

10.3390/molecules28031196

中图分类号：

Q5 [生物化学]; Q7 [分子生物学];

学科分类号：

071010 ; 081704 ;

摘要：

Novel 13 alpha-estrone derivatives have been synthesized via direct arylation of the phenolic hydroxy function. Chan-Lam couplings of arylboronic acids with 13 alpha-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.

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页数：17

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