This study deals with the design of original benzofuran–chalcone hybrids as anticancer agents. First, the reaction of 6-methoxysaliciylaldehyde with chloroacetone and potassium carbonate was used to prepare 1-(6-methoxy-1-benzofuran-2-yl) ethanone (1) as a starting reagent. A novel series of chalcone derivatives 3a–h, obtained through Claisen–Schmidt condensation with aromatic aldehydes 2a–h containing 6-methoxy benzofuran moiety, was designed, synthesized, and evaluated in terms of anticancer activities. The synthesized compounds 3a–h were tested against two MDA-MB-231 (human breast cancer cell line) and A549 (human lung cancer cell line) in order to detect anticancer activity by MTT Assay. The results revealed that 2-acetylbenzofuran-chalcone hybrids have an anticancer effect, especially with the phenolate salt of chalcone derivative 3e which shows cytotoxic effects on lung cancer cells. These observations showed that novel hybrid chalcone derivatives with a phenolate and methoxy linked 2-acetylbenzofuran prodrug strategy would be an important and easy method to increase water solubility and anticancer activity.

本研究涉及作为抗癌剂的原始苯并呋喃-查耳酮杂化物的设计。首先，6-甲氧基水杨醛与氯丙酮和碳酸钾反应制备1-(6-甲氧基-1-苯并呋喃-2-基)乙酮(1)作为起始试剂。设计、合成了一系列新型查耳酮衍生物 3a-h，通过克莱森-施密特与含有 6-甲氧基苯并呋喃部分的芳香醛 2a-h 缩合获得，并在抗癌活性方面进行了评估。合成的化合物 3a-h 针对两种 MDA-MB-231（人乳腺癌细胞系）和 A549（人肺癌细胞系）进行了测试，以通过 MTT 分析检测抗癌活性。结果表明，2-乙酰苯并呋喃-查耳酮杂化物具有抗癌作用，尤其是查尔酮衍生物 3e 的酚盐对肺癌细胞显示出细胞毒性作用。这些观察结果表明，具有酚盐和甲氧基连接的 2-乙酰苯并呋喃前药策略的新型杂化查尔酮衍生物将是提高水溶性和抗癌活性的重要且简单的方法。