由 2,4-二氨基-1,3,5-三嗪和 2-亚氨基香豆素和香豆素组成的杂化分子。合成与细胞毒性性质。
Hybrid Molecules Composed of 2,4-Diamino-1,3,5-triazines and 2-Imino-Coumarins and Coumarins. Synthesis and Cytotoxic Properties.
机构信息
Department of Chemical Technology of Drugs, Faculty of Pharmacy, Medical University of Gdańsk, 80-416 Gdańsk, Poland.
Department of Pharmaceutical and Medicinal Chemistry, Institute of Pharmacy, University of Greifswald, L.-F.-Jahn Str., D-17489 Greifswald, Germany.
出版信息
Molecules. 2018 Jul 3;23(7):1616. doi: 10.3390/molecules23071616.
A series of 2-imino-2-chromen-3-yl-1,3,5-triazine compounds ⁻, which are namely hybrids of 2,4-diamino-1,3,5-triazines and 2-imino-coumarins, was synthesized by reacting 2-(4,6-diamine-1,3,5-triazin-2-yl)acetonitriles ⁻ with 2-hydroxybenzaldehydes. After this, upon heating in aqueous DMF, 2-imino-2-chromen-3-yl-1,3,5-triazines and were converted into the corresponding 2-chromen-3-yl-1,3,5-triazines and , which are essentially hybrids of 2,4-diamino-1,3,5-triazines and coumarins. The in vitro anticancer activity of the newly prepared compounds was evaluated against five human cancer cell lines: DAN-G, A-427, LCLC-103H, SISO and RT-4. The greatest cytotoxic activity displayed 4-[7-(diethylamino)-2-imino-2-chromen-3-yl]-6-(4-phenylpiperazin-1-yl)-1,3,5-triazin-2-amine (11, IC in the range of 1.51⁻2.60 μM).
一系列 2-亚氨基-2-色烯基-1,3,5-三嗪化合物⁻，它们是 2,4-二氨基-1,3,5-三嗪和 2-亚氨基香豆素的混合物，通过将 2-(4,6-二氨基-1,3,5-三嗪-2-基)乙腈⁻与 2-羟基苯甲醛反应合成。之后，在水合 DMF 中加热，2-亚氨基-2-色烯基-1,3,5-三嗪⁻和⁻转化为相应的 2-色烯基-1,3,5-三嗪⁻和⁻，它们实质上是 2,4-二氨基-1,3,5-三嗪和香豆素的混合物。新制备的化合物的体外抗癌活性针对五种人癌细胞系进行了评估：DAN-G、A-427、LCLC-103H、SISO 和 RT-4。显示最大细胞毒性活性的是 4-[7-(二乙氨基)-2-亚氨基-2-色烯基]-6-(4-苯哌嗪-1-基)-1,3,5-三嗪-2-胺（11，IC 在 1.51⁻2.60 μM 范围内）。
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