Guangxi Key Laboratory of Electrochemical and Magnetochemical Functional Materials, Collaborative Innovation Center for Exploration of Hidden Nonferrous Metal Deposits and Development of New Materials in Guangxi (College of Chemistry and Bioengineering), Guilin University of Technology, Guilin 541004, China.
College of Chemistry and Engineering, Guangxi Normal University for Nationalities, Chongzuo 532200, China.
Molecules. 2017 Oct 25;22(11):1813. doi: 10.3390/molecules22111813.
Five novel compounds, methyl 5-(acetyloxy)-1-(6-bromo-2-pyridinyl)-1-pyrazole-3-carboxylate (), methyl 1-(6-bromo-2-pyridinyl)-5-hydroxy-1H-pyrazole-3-carboxylate (), Trimethyl 1,1',1''-tris(6-bromo-2-pyridinyl)-5,5''-dihydroxy-5'-oxo-1',5'-dihydro-1H,1''H-4,4': 4',4''-terpyrazole-3,3',3''-tricarboxylate (H₂L¹, ), [Cu₂(L²)₂]·CH₃OH (), H₂L·CH₃CN () were synthesized. Compounds - characterized by elemental analysis, IR, and X-ray single-crystal diffraction. And - were also characterized by ¹H NMR, C NMR and ESI-MS. The H₂L¹, H₂L² were formed by in-situ reaction. H₂L² and H₂L are mesomer compounds which have two chiral carbons. The antitumor activity of compounds - against BEL-7404, HepG2, NCI-H460, T-24, A549 tumor cell lines were screened by methylthiazolyl tetrozolium (MTT) assay. The compounds , showed weakly growth inhibition on the HepG2 cell lines. The HepG2 and A549 cell lines showed higher sensitivity to compound , while the IC values are 10.66, 28.09 μM, respectively. It is worth noting that compounds - did not show cytotoxicity to human normal liver cell line HL-7702, suggesting its cytotoxic selectivity on these tumor cell lines.
合成了五个新化合物，分别为 5-(乙酰氧基)-1-(6-溴吡啶-2-基)-1-吡唑-3-羧酸甲酯 ()、1-(6-溴吡啶-2-基)-5-羟基-1H-吡唑-3-羧酸甲酯 ()、1,1',1''-三(6-溴吡啶-2-基)-5,5''-二羟基-5'-氧代-1',5'-二氢-1H,1''H-4,4':4',4''-三联吡唑-3,3',3''-三羧酸甲酯 (H₂L¹, )、[Cu₂(L²)₂]·CH₃OH ()、H₂L·CH₃CN ()。通过元素分析、红外光谱和 X 射线单晶衍射对化合物 - 进行了表征。通过 ¹H NMR、C NMR 和 ESI-MS 对化合物 - 进行了表征。H₂L¹、H₂L²是通过原位反应形成的。H₂L²和 H₂L 是具有两个手性碳原子的mesomer 化合物。通过甲基噻唑基四唑 (MTT) 法筛选了化合物 - 对 BEL-7404、HepG2、NCI-H460、T-24、A549 肿瘤细胞系的抗肿瘤活性。化合物 、 对 HepG2 细胞系表现出较弱的生长抑制作用。HepG2 和 A549 细胞系对化合物 表现出较高的敏感性，IC 值分别为 10.66、28.09 μM。值得注意的是，化合物 - 对人正常肝细胞系 HL-7702 没有表现出细胞毒性，表明其对这些肿瘤细胞系具有细胞毒性选择性。
