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Citation: ZHANG Chenglu, GUO Yang, WU Yifei, ZHU Chang'an, QU Ruifeng, SUN Lijie, WENG Xue, CHAI Jinhua. Synthesis and Biological Activities of 3-Aliphatic-1,2,4-Triazole[3,4-b]-1,3,4-Thiatriazole Derivatives Containing Pyridine Unit[J]. Chinese Journal of Applied Chemistry, ;2014, 31(12): 1419-1427. doi: 10.3724/SP.J.1095.2014.40096 shu

Synthesis and Biological Activities of 3-Aliphatic-1,2,4-Triazole[3,4-b]-1,3,4-Thiatriazole Derivatives Containing Pyridine Unit

1.
Liaoning Provincial key Laboratory of Biotechnology and Drug Discovery, School of Chemistry and Chemical Engineering, Liaoning Normal University, Dalian 116029, China

Corresponding author: ZHANG Chenglu,
Received Date: 27 March 2014
Available Online: 28 May 2014
Fund Project: 辽宁省教育厅科学技术项目资助(2009A426) (2009A426)

3-Aliphatic-1,2,4-triazole derivatives 1a~1f were synthesized through the reaction of six kinds of fatty acids with diaminothiourea,in which compounds 1e and 1f were first synthesized.In the presence of phosphorus oxychloride,compounds 1a~1f reacted with 4-pyridine carboxylic acid and 2,6-pyridine dicarboxylic acid,respectively.The 12 kinds of aliphatic triazoles,thiadiazoles 2a~2f and 3a~3f were synthesized in high yields for the first time.In order to study the influence of 3-aliphatic group and pyridine,compounds 5,6,7a~7c and 8a~8c without pyridine units were also synthesized.The target compounds were well characterized by IR,¹H NMR and HRMS.In the biotic screening test,the inhibitory properties of Cdc25B and PTP1B were explored.The results show that compounds 3b,3d,3e and 3f have good inhibition activity against Cdc25B with IC₅₀ values of(1.12±0.27),(2.72±1.07),(0.72±0.05) and(4.97±0.93) mg/L,respectively;compounds 2b,3d,and 5 exhibit higher inhibition activity against PTP1B with IC₅₀ values of(0.98±0.13),(1.33±0.11),(2.18±0.20) mg/L,respectively.
- aliphatic-triazole,
- pyridine unit,
- biotic screening test,
- Cdc25B
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