Chinese Journal of Organic Chemistry >
Synthesis and Biological Activities of 1,3,4-Thiadiazole Triazene Compound
Received date: 2018-09-03
Revised date: 2018-10-27
Online published: 2018-12-21
Supported by
Project supported by the National Natural Science Foundation of China (No.J1210060),the Science and Technology Planning Project of Henan Province (No.0624420031) and the Basic Research Development Program of Henan Province (No.022463001).
Using the splicing principle of combining the pharmacological group triazene with 1,3,4-thiadiazole, 15 unreported 1,3,4-thiadiazole triazene derivatives were synthesized. The structures of the compounds were determined by nucleated magnetic resonance spectroscopy (NMR), infrared spectroscopy (IR) and high-resolution mass spectrometry (HRMS). By using the typical triazene drug dacarbazine (DTIC) and drug 5-fluorouracil (5-FU) as a reference, the activity detections of human esop-hageal cancer cells (EC109), human gastric cancer cells (MGC803), and human prostate cancer cells (PC-3) were carried out. The results showed that some compounds inhibited human gastric cancer cells (MGC803) more strongly than dacarbazine (DTIC), and the IC50 values of compounds 2-(3-methyanilino)-5-[4-(3,3-dimethyltriazol-1-yl) phenyl]-1,3,4-thiadiazole (8c), 2-(2-methoxyanilino)-5-[4-(3,3-dimethyltriazol-1-yl) phenyl]-1,3,4-thiadiazole (8f), and 2-(3,4-dichloroanilino)-5-[4-(3,3-di-methyltriazol-1-yl) phenyl]-1,3,4-thiadiazole (8l) were lower than those of 5-fluorouracil with 5.3, 6.5 and 6.3 μmol/L, respec-tively. Some compounds inhibited human prostate cancer cells (PC-3) more strongly than dacarbazine (DTIC), and the IC50 value of 8l is lower than that of 5-fluorouracil with 13.5 μmol/L.
Zhang Mingqian , Liu Binkai , Lei Qiang , Yan Jingdong , Zhao Zhongyu , Long Yue . Synthesis and Biological Activities of 1,3,4-Thiadiazole Triazene Compound[J]. Chinese Journal of Organic Chemistry, 2019 , 39(4) : 1064 -1069 . DOI: 10.6023/cjoc201809003
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