Cytotoxicity and structure-activity relationships of four alpha-N-heterocyclic thiosemicarbazone derivatives crystal structure of 2-acetylpyrazine thiosemicarbazone.
A series of thiosemicarbazone ligands, HL(1) (2-acetylpyrazine thiosemicarbazone), HL(2) (2-acetylpyrazine N(4)-methylthiosemicarbazone), HL(3) (2-benzoylpyridine thiosemicarbazone) and HL(4) (2-benzoylpyridine N(4)-methylthiosemicarbazone), have been synthesized. The crystal structure of HL(1) 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, HL(4) with substitution at N(4) position in thiosemicarbazone along with 2-benzoylpyridine is the most active thiosemicarbazone ligand with IC(50)=0.002microm in the K562 leucocythemia cell line and 0.138microm in the BEL7402 liver cancer cell line, respectively.
Li
Ming-Xue
MX
Institute of Molecular and Crystal Engineering, Henan University, Kaifeng, PR China. limingxue@henu.edu.cn
Chen
Chun-Ling
CL
Ling
Chun-Sheng
CS
Zhou
Jing
J
Ji
Bian-Sheng
BS
Wu
Yan-Juan
YJ
Niu
Jing-Yang
JY
D000970:Antineoplastic Agents / Q000737:chemistry / Q000633:toxicity*; D045744:Cell Line, Tumor; D018360:Crystallography, X-Ray; D006801:Humans; D013329:Structure-Activity Relationship; D013882:Thiosemicarbazones / Q000138:chemical synthesis / Q000737:chemistry / Q000633:toxicity*
C541531:2-benzoylpyridine N(4)-methylthiosemicarbazone; D000970:Antineoplastic Agents; D013882:Thiosemicarbazones