Cytotoxicity and structure-activity relationships of four α-N-heterocyclic thiosemicarbazone derivatives crystal structure of 2-acetylpyrazine thiosemicarbazone
Cytotoxicity and structure-activity relationships of four α-N-heterocyclic thiosemicarbazone derivatives crystal structure of 2-acetylpyrazine thiosemicarbazone
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DOI：
10.1016/j.bmcl.2009.03.135
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发表时间：
2009-05-15
影响因子：
2.7
通讯作者：
Niu, Jing-Yang
中科院分区：
文献类型：
--
作者：
Li, Ming-Xue;Chen, Chun-Ling;Niu, Jing-Yang
合成了一系列缩氨基硫脲配体HL 1（2-乙酰基吡嗪缩氨基硫脲）、HL 2（2-乙酰基吡嗪N（4）-甲基缩氨基硫脲）、HL 3（2-苯甲酰基吡啶缩氨基硫脲）和HL 4（2-苯甲酰基吡啶N（4）-甲基缩氨基硫脲）。用单晶X射线衍射法测定了HL-1的晶体结构。氢键将不同的组分连接起来以稳定晶体结构。用K562白血病细胞株和BEL 7402肝癌细胞株检测了4种配体的抗肿瘤活性。所有缩氨基硫脲类化合物均具有明显的抗肿瘤活性。配体上不同的取代基表现出不同的抗肿瘤活性。通过与其它缩氨基硫脲类化合物的比较，发现N（4）位沿着被2-苯甲酰基吡啶取代的HL 4是活性最高的缩氨基硫脲配体，其对白血病细胞系K 562和肝癌细胞系BEL 7402的IC_（50）分别为0.002 μ m和0.138 μ m。(C)2009爱思唯尔有限公司版权所有。
A series of thiosemicarbazone ligands, HL1 (2-acetylpyrazine thiosemicarbazone), HL2 (2-acetylpyrazine N(4)-methylthiosemicarbazone), HL3 (2-benzoylpyridine thiosemicarbazone) and HL4 (2-benzoylpyridine N(4)-methylthiosemicarbazone), have been synthesized. The crystal structure of HL1 has been determined by single-crystal X-ray diffraction. Hydrogen bonds link the different components to stabilize the crystal structure. The antitumor activity of the four ligands were tested against K562 leucocythemia and BEL7402 liver cancer cell lines. All the thiosemicarbazones showed significant antitumor activity. Different substituents on the ligands show different levels of antitumor activity. By comparison with the other thiosemicarbazone species studied, HL4 with substitution at N(4) position in thiosemicarbazone along with 2-benzoylpyridine is the most active thiosemicarbazone ligand with IC50 = 0.002 mu m in the K562 leucocythemia cell line and 0.138 mu m in the BEL7402 liver cancer cell line, respectively. (C) 2009 Elsevier Ltd. All rights reserved.