Zhu Jing-Jing, Jiang Jian-Guo
Department of Sugar Engineering, College of Food and Bioengineering, South China University of Technology, Guangzhou, 510640, China.
Mol Nutr Food Res. 2018 Jul;62(14):e1701073. doi: 10.1002/mnfr.201701073. Epub 2018 Jun 19.
Coumarins are fused benzene and pyrone ring systems with a wide spectrum of bioactivities, including antitumor, anti-inflammation, antiviral, and antibacterial effects. In this paper, the current development of coumarin-based drugs is introduced, and their structure-activity relationship is discussed by reviewing the relevant literature published in the past 20 years. Coumarin molecules can be customized by the target site to prevent systemic side effects by virtue of structural modification. The ortho-phenolic hydroxyl on the benzene ring has remarkable antioxidant and antitumor activities. Coumarins with aryl groups at the C-4 position have good activities in anti-HIV, antitumor, anti-inflammation, and analgesia. C-3 phenylcoumarins have strong anti-HIV and antioxidant effects. Tetracycline pyranocoumarins can significantly inhibit HIV; osthol structural analogues have antimicrobial activity. Praeruptorin C and its derivatives play an important role in lowering blood pressure and dilating coronary arteries, and khellactone derivatives have significant inhibitory effects on AIDS, cancer, and cardiovascular diseases. It is concluded that the specific site on the core structure of coumarin exhibits one or more activities due to the electronic or steric effects of the substituents. This review is intended to be conducive to rational design and development of more active and less toxic agents with a coumarin scaffold.
香豆素是由苯环和吡喃酮环稠合而成的体系，具有广泛的生物活性，包括抗肿瘤、抗炎、抗病毒和抗菌作用。本文介绍了基于香豆素的药物的当前发展情况，并通过回顾过去20年发表的相关文献来讨论它们的构效关系。香豆素分子可以根据靶点进行定制，通过结构修饰来防止全身副作用。苯环上的邻位酚羟基具有显著的抗氧化和抗肿瘤活性。在C-4位带有芳基的香豆素在抗HIV、抗肿瘤、抗炎和镇痛方面具有良好的活性。C-3苯基香豆素具有很强的抗HIV和抗氧化作用。四环吡喃香豆素能显著抑制HIV；蛇床子素结构类似物具有抗菌活性。前胡丙素及其衍生物在降低血压和扩张冠状动脉方面发挥重要作用，而凯林内酯衍生物对艾滋病、癌症和心血管疾病具有显著的抑制作用。得出的结论是，由于取代基的电子或空间效应，香豆素核心结构上的特定位点表现出一种或多种活性。本综述旨在有助于合理设计和开发更多具有香豆素骨架的活性更高、毒性更小的药物。
