Department of Chemical Technology of Drugs, Medical University of Gdańsk, Al. Gen. J. Hallera 107, 80-416 Gdańsk, Poland.
Department of Pharmaceutical and Medicinal Chemistry, Institute of Pharmacy, University of Greifswald, F.-L. Jahn Strasse 17, D-17489 Greifswald, Germany.
Molecules. 2018 Jun 20;23(6):1497. doi: 10.3390/molecules23061497.
A small library of novel quinoline-3-carbaldehyde hydrazones (Series 1), acylhydrazones (Series 2), and arylsulfonylhydrazones (Series 3) bearing either a 1,2,4-triazole or benzotriazole ring at position 2 was prepared, characterized by elemental analyses and IR, NMR, and MS spectra, and then subjected to in vitro cytotoxicity studies on three human tumor cell lines: DAN-G, LCLC-103H, and SISO. In general, compounds , , and substituted with a 1,2,4-triazole ring proved to be inactive, whereas the benzotriazole-containing quinolines , , and elicited pronounced cancer cell growth inhibitory effects with IC values in the range of 1.23⁻7.39 µM. The most potent 2-(1-benzotriazol-1-yl)-3-[2-(pyridin-2-yl)hydrazonomethyl]quinoline () showed a cytostatic effect on the cancer cell lines, whereas ′-[(2-(1-benzotriazol-1-yl)quinolin-3-yl)methylene]-benzohydrazide () and ′-[(2-1-benzotriazol-1-yl)quinolin-3-yl)methylene]-naphthalene-2-sulfonohydrazide () exhibited selective activity against the pancreas cancer DAN-G and cervical cancer SISO cell lines. Based on the determined IC values, the compound seems to be leading compound for further development as anticancer agent.
我们制备了一系列新型的喹啉-3-甲酰腙（系列 1）、酰腙（系列 2）和芳磺酰腙（系列 3），这些化合物在 2 位上都带有 1,2,4-三唑或苯并三唑环，通过元素分析、IR、NMR 和 MS 光谱对其进行了表征，然后对三种人肿瘤细胞系：DAN-G、LCLC-103H 和 SISO 进行了体外细胞毒性研究。一般来说，带有 1,2,4-三唑环的化合物 、 和 没有活性，而含有苯并三唑的喹啉 、 和 则表现出明显的癌细胞生长抑制作用，IC 值在 1.23⁻7.39 µM 范围内。最有效的 2-(1-苯并三唑-1-基)-3-[2-(吡啶-2-基)腙基甲基]喹啉 () 对癌细胞系表现出细胞抑制作用，而 ′-[(2-(1-苯并三唑-1-基)喹啉-3-基)亚甲基]-苯甲酰肼 () 和 ′-[(2-1-苯并三唑-1-基)喹啉-3-基)亚甲基]-萘-2-磺酰肼 () 对胰腺癌 DAN-G 和宫颈癌 SISO 细胞系表现出选择性活性。根据确定的 IC 值，化合物 似乎是作为抗癌剂进一步开发的先导化合物。
