College of Chemistry, Jilin University, 2699 Qianjin Street, Changchun 130012, PR China.
College of Chemistry, Jilin University, 2699 Qianjin Street, Changchun 130012, PR China.
Ultrason Sonochem. 2017 May;36:343-353. doi: 10.1016/j.ultsonch.2016.12.011. Epub 2016 Dec 9.
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 β-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 NMR and C 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-HSL as a positive control. The compounds 8a, 8c and 8f exhibited considerable levels of inhibitory activity against violacein production, and IC values were 217±19, 223±20 and 42.8±4.5μM, respectively, which highlighted the potential of these compounds as lead structures for further research towards the development of novel QS inhibitors.
研究了 1,4-二取代 1,2,3-三唑衍生物的高效合成方法。以各种末端异恶唑醚炔烃和β-胸苷叠氮衍生物为原料，在超声辅助条件下，以醋酸铜和抗坏血酸钠为催化剂，通过 1,3-偶极环加成反应，以 84-96%的产率合成了含有异噁唑和胸苷结构的 1,4-二取代 1,2,3-三唑。所有目标化合物均通过高分辨质谱（HRMS）、傅里叶变换红外光谱（FT-IR）、核磁共振氢谱（H NMR）和核磁共振碳谱（C NMR）进行了表征。此外，根据它们对紫罗酮产生的抑制作用，用 Chromobacterium violaceum（C. Violaceum CV026）评估了合成化合物的群体感应抑制活性，以 C-HSL 化合物作为阳性对照。化合物 8a、8c 和 8f 对紫罗酮产生表现出相当水平的抑制活性，IC 值分别为 217±19、223±20 和 42.8±4.5μM，这突出了这些化合物作为进一步研究新型 QS 抑制剂的潜在先导结构。
