Anthraquinones are of significant interest due to their biological activity, coloring properties, and synthetic applications. Here, we describe a mild and convenient method for modification of 1-ethynyl-4-hydroxyanthraquinone that was obtained from the Sonogashira cross-coupling reaction of 1-hydroxy-4-iodoanthraquinone with alkynes. The copper(I) catalyzed one-pot three-component reaction (A³-coupling) of the new 1-ethynyl-4-hydroxyanthraquinone with secondary amines and formaldehyde was the main approach for the synthesis of nitrogen-substituted 1-[3-(amino)prop-1-ynyl]-4-hydroxyanthraquinones. The influence of different substituents in the amine on reaction rate and yield has been evaluated. The cytotoxicity of 1-ethynyl-4-hydroxyanthraquinones was assessed using the conventional MTT assay. Among all compounds synthesized, anthraquinone-propargylamine derivatives 28, 29, 30, and 34 possess the most promising cytotoxic potential towards glioblastoma cancer cells; compounds 14 and 19 shown selectivity towards the prostate cancer cells DU-145, and 18, 24 — on breast cancer cell line MCF-7. The grown inhibition on these cancer cells by compounds 18 and 24 was comparable to those of standard drug Doxorubicin. Molecular modeling of new anthraquinone derivatives in DNA G-quadruplex binding sites was performed to help understand the observed SAR trends.

蒽醌类化合物因其生物活性、着色特性和合成应用而备受关注。在这里，我们描述了一种温和方便的方法来修饰 1-乙炔基-4-羟基蒽醌，该方法是从1-羟基-4-碘蒽醌与炔烃的Sonogashira交叉偶联反应中获得的。铜(I)催化的一锅三组分反应(A ³-偶联）新的 1-乙炔基-4-羟基蒽醌与仲胺和甲醛是合成氮取代的 1-[3-（氨基）丙-1-炔基]-4-羟基蒽醌的主要方法。已评估胺中不同取代基对反应速率和产率的影响。1-ethynyl-4-hydroxyanthraquinones 的细胞毒性使用常规 MTT 测定法进行评估。中合成的所有化合物，蒽醌衍生物炔丙胺28，29，30，和34具有朝向成胶质细胞瘤肿瘤细胞的最有希望的细胞毒性潜力; 化合物14和19显示出对前列腺癌细胞 DU-145 和18 的选择性, 24 — 在乳腺癌细胞系 MCF-7 上。化合物18和24对这些癌细胞的生长抑制与标准药物多柔比星的抑制相当。对 DNA G-四链体结合位点中的新型蒽醌衍生物进行了分子建模，以帮助了解观察到的 SAR 趋势。