Dilović Ivica, Rubcić Mirta, Vrdoljak Visnja, Kraljević Pavelić Sandra, Kralj Marijeta, Piantanida Ivo, Cindrić Marina
Faculty of Science, Chemistry Department, Horvatovac 102(a), 10000 Zagreb, Croatia.
Bioorg Med Chem. 2008 May 1;16(9):5189-98. doi: 10.1016/j.bmc.2008.03.006. Epub 2008 Mar 6.
The paper describes synthesis of several novel thiosemicarbazone derivatives. Furthermore, crystal and molecular structure of 4-diethylamino-salicylaldehyde 4-phenylthiosemicarbazone revealed planarity of conjugated aromatic system, which suggested the possibility of DNA binding by intercalation, especially for here studied naphthalene derivatives. However, here presented DNA binding studies excluded this mode of action. Physicochemical and structural properties of novel derivatives were compared with previously studied analogues, taken as reference compounds, revealing distinctive differences. In addition, novel thiosemicarbazone derivatives (1, 2 and 5-8) clearly display stronger antiproliferative activity on five tumor cell lines than the reference compounds 3 and 4, which supports their further investigation as potential antitumor agents.
该论文描述了几种新型硫代氨基脲衍生物的合成。此外，4-二乙氨基水杨醛4-苯基硫代氨基脲的晶体和分子结构揭示了共轭芳香体系的平面性，这表明通过嵌入作用与DNA结合的可能性，特别是对于此处研究的萘衍生物。然而，此处呈现的DNA结合研究排除了这种作用模式。将新型衍生物的物理化学和结构性质与先前研究的类似物（作为参考化合物）进行比较，发现了明显的差异。此外，新型硫代氨基脲衍生物（1、2和5-8）在五种肿瘤细胞系上显示出比参考化合物3和4更强的抗增殖活性，这支持将它们作为潜在抗肿瘤药物进行进一步研究。
