Department of Organic Chemistry, University of Szeged, Dóm tér 8, H-6720 Szeged, Hungary.
Department of Pharmacodynamics and Biopharmacy, University of Szeged, Eötvös u. 6., H-6720 Szeged, Hungary.
Steroids. 2020 Dec;164:108731. doi: 10.1016/j.steroids.2020.108731. Epub 2020 Sep 16.
13α-Estrones are of great value owing to their potent multiple bioactivity, including anticancer activity. 3-OH or 3-OBn derivatives of 2- or 4-[(subst.) phenyl]-13α-estrone as potential antiproliferative agents have been synthesized via facile, microwave-induced, Pd-catalyzed Suzuki-Miyaura coupling. 2- or 4-Halogenated 13α-estrone derivatives have been reacted with (4-subst.)phenylboronic acids using Pd(PPh) as catalyst. The nature of para substituents at the introduced phenyl group did not influence the outcome of couplings. Certain newly synthesized compounds displayed substantial antiproliferative action against human adherent cancer cell lines of gynecological origin. Important structure-activity relationships were revealed, which might be helpful in the design of potent and selective anticancer derivatives based on the hormonally inactive 13α-estrane core.
13α-雌酮因其强大的多种生物活性而具有重要价值，包括抗癌活性。通过简便的微波诱导钯催化 Suzuki-Miyaura 偶联，合成了 2-或 4-[(取代基)苯基]-13α-雌酮的 3-OH 或 3-OBn 衍生物作为潜在的抗增殖剂。用 Pd(PPh)作为催化剂，将 2-或 4-卤代 13α-雌酮衍生物与(4-取代基)苯基硼酸反应。引入的苯基上对位取代基的性质不影响偶联的结果。某些新合成的化合物对妇科来源的人贴壁癌细胞系表现出显著的抗增殖作用。揭示了重要的构效关系，这可能有助于基于无激素活性的 13α-雌烷核设计有效的选择性抗癌衍生物。
