Ultrasonic-assisted synthesis of 1,4-disubstituted 1,2,3-triazoles via various terminal acetylenes and azide and their quorum sensing inhibition

作者：Zhang, Da-wei; Zhang, Yu-min; Li, Jing; Zhao, Tian-qi; Gu, Qiang^*; Lin, Feng^*

来源：Ultrasonics Sonochemistry, 2017, 36: 343-353.

DOI：10.1016/j.ultsonch.2016.12.011

• 1,2,3-Triazole
• Isoxazole
• Thymidine
• 1,3-Dispolar cycloaddition
• Ultrasonic heating
• Quorum sensing

An efficient synthesis of 1,4-disubstituted 1,2,3-triazole derivatives was studied. 1,4-Disubstituted 1,2, 3-triazoles containing isoxazole and thymidine structures were synthesized in 84-96% yields starting from various terminal isoxazole ether alkynes and beta-thymidine azide derivatives via a 1,3-dispolar cycloaddition using copper acetate, sodium ascorbate as the catalyst under ultrasonic assisted condition. All the target compounds were characterized by HRMS, FT-IR, H-1 NMR and C-13 NMR spectroscopy. Furthermore, the quorum sensing inhibitory activities of synthesized compounds were evaluated with Chromobacterium violaceum (C. Violaceum CV026) based on their inhibition of violacein production, with compound C-10-HSL as a positive control. The compounds 8a, 8c and 8f exhibited considerable levels of inhibitory activity against violacein production, and IC50 values were 217 +/- 19, 223 +/- 20 and 42.8 +/- 4.5 mu M, respectively, which highlighted the potential of these compounds as lead structures for further research towards the development of novel QS inhibitors.

• 出版日期2017-5
• 单位吉林大学