新型双（香豆素-1,2,3-三唑基）苯并化合物和香豆素-1,2,3-三唑基-芳基杂化衍生物的设计、合成、光谱特性和体外细胞抑制评估。
Design, Synthesis, Spectroscopic Characterisation and In Vitro Cytostatic Evaluation of Novel Bis(coumarin-1,2,3-triazolyl)benzenes and Hybrid Coumarin-1,2,3-triazolyl-aryl Derivatives.
机构信息
Department of General and Inorganic Chemistry, Faculty of Chemical Engineering and Technology, University of Zagreb, Marulićev trg 19, 10000 Zagreb, Croatia.
Fidelta Ltd., Prilaz baruna Filipovića 29, 10000 Zagreb, Croatia.
出版信息
Molecules. 2022 Jan 19;27(3):637. doi: 10.3390/molecules27030637.
In this work, a series of novel 1,2,3-triazolyl-coumarin hybrid systems were designed as potential antitumour agents. The structural modification of the coumarin ring was carried out by Cu(I)-catalysed Huisgen 1,3-dipolar cycloaddition of 7-azido-4-methylcoumarin and terminal aromatic alkynes to obtain 1,4-disubstituted 1,2,3-triazolyl-coumarin conjugates -, bis(1,2,3-triazolyl-coumarin)benzenes - and coumarin-1,2,3-triazolyl-benzazole hybrids -. The newly synthesised hybrid molecules were investigated for in vitro antitumour activity against five human cancer cell lines, colon carcinoma HCT116, breast carcinoma MCF-7, lung carcinoma H 460, human T-lymphocyte cells CEM, cervix carcinoma cells HeLa, as well as human dermal microvascular endothelial cells (HMEC-1). Most of these compounds showed moderate to pronounced cytotoxic activity, especially towards MCF-7 cell lines with IC = 0.3-32 μM. In addition, compounds - and - were studied by UV-Vis absorption and fluorescence spectroscopy and their basic photophysical parameters were determined.
在这项工作中，设计了一系列新型的 1,2,3-三唑基香豆素杂合体系作为潜在的抗肿瘤剂。通过 Cu(I)催化的 7-叠氮基-4-甲基香豆素和末端芳香炔的 Huisgen 1,3-偶极环加成反应对香豆素环进行结构修饰，得到 1,4-二取代 1,2,3-三唑基香豆素共轭物 -、双（1,2,3-三唑基香豆素）苯 - 和香豆素-1,2,3-三唑基苯并唑杂合体 -。对新合成的杂合分子进行了体外抗肿瘤活性研究，针对五种人癌细胞系，结肠癌细胞 HCT116、乳腺癌 MCF-7、肺癌 H460、人 T 淋巴细胞 CEM、宫颈癌 HeLa 以及人皮肤微血管内皮细胞（HMEC-1）进行了检测。这些化合物大多数表现出中等至显著的细胞毒性活性，尤其是对 MCF-7 细胞系的 IC = 0.3-32 μM。此外，还通过紫外可见吸收和荧光光谱研究了化合物 - 和 -，并确定了它们的基本光物理参数。
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