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.
Institute of Molecular and Crystal Engineering, Henan University, Kaifeng, PR China. limingxue@henu.edu.cn
Ming-Xue
MX
Li
Chun-Ling
CL
Chen
Chun-Sheng
CS
Ling
Jing
J
Zhou
Bian-Sheng
BS
Ji
Yan-Juan
YJ
Wu
Jing-Yang
JY
Niu
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