Lin Ding, Wang Long, Yan Zhongzhong, Ye Jiao, Hu Aixi, Liao Hongdong, Liu Juan, Peng Junmei
College of Chemistry and Chemical Engineering, Hunan University Changsha 410082 China
College of Biology, Hunan University Changsha 410082 China
RSC Adv. 2018 Oct 5;8(60):34331-34342. doi: 10.1039/c8ra04773a. eCollection 2018 Oct 4.
5-Arylbenzofuran neolignans, a newfound class of natural products, were reported to possess several kinds of pharmacological activities. To solve the lack of natural sources and promote the research of 5-arylbenzofuran neolignans in all fields, an available semi-synthesis methodology of 5-arylbenzofuran neolignans was developed, and a detailed structural modification was conducted. In the meantime, a one-pot process of Waker-type cyclization and Wacker-type oxidation was developed. To explore the potential of 5-arylbenzofuran neolignans as bioactive substances, 5-arylbenzofuran neolignans and their derivatives were evaluated for their cytotoxicity. As a result, a preliminary structure-activity relationship was obtained. Most derivatives revealed low cytotoxic effects suggesting that they were relatively safer than the natural 5-arylbenzofuran neolignan. Several derivatives showed high cytotoxicities which were found to be closely associated with apoptosis-inducing. The selectivity assay for cytotoxicity showed tumor cells were more sensitive to the promising compounds than normal cells.
5-芳基苯并呋喃新木脂素是一类新发现的天然产物，据报道具有多种药理活性。为了解决天然来源不足的问题并推动5-芳基苯并呋喃新木脂素在各个领域的研究，开发了一种可行的5-芳基苯并呋喃新木脂素半合成方法，并进行了详细的结构修饰。同时，开发了一种Waker型环化和Wacker型氧化的一锅法。为了探索5-芳基苯并呋喃新木脂素作为生物活性物质的潜力，对5-芳基苯并呋喃新木脂素及其衍生物进行了细胞毒性评估。结果，获得了初步的构效关系。大多数衍生物显示出低细胞毒性作用，表明它们比天然的5-芳基苯并呋喃新木脂素相对更安全。几种衍生物表现出高细胞毒性，发现它们与诱导凋亡密切相关。细胞毒性的选择性测定表明，肿瘤细胞对有前景的化合物比正常细胞更敏感。
