State Key Laboratory Breeding Base of Green Pesticide and Agricultural Bioengineering, Key Laboratory of Green Pesticide and Agricultural Bioengineering, Ministry of Education, Centre for Research and Development of Fine Chemicals, Guizhou University, Guiyang, 550025, China.
Mol Divers. 2018 Aug;22(3):657-667. doi: 10.1007/s11030-018-9821-8. Epub 2018 Mar 24.
A series of structurally novel 3-thioether-1-(quinazolin-4-yl)-1H-1,2,4-triazol-5-amine derivatives (7a-7r) were designed and synthesized based on a pharmacophore hybrid approach, and screened for their antibacterial and antifungal activities in vitro. All the target compounds were fully characterized through [Formula: see text]H NMR, [Formula: see text]C NMR and HRMS spectra. Among them, the structure of compound 7b was further confirmed via single-crystal X-ray diffraction analysis. The obtained results indicated that several target compounds demonstrated notable inhibition activities against tested phytopathogenic bacteria, using a turbidimetric method. For example, compounds 7d, 7g and 7i exhibited EC[Formula: see text] (half-maximal effective concentration) values of 46.9, 47.8 and 43.2 µg/mL, respectively, against the bacterium Xanthomonas axonopodis pv. citri (Xac), which were more potent than commercial agrobactericide Bismerthiazol (56.9 µg/mL). Moreover, EC[Formula: see text] values of compounds 7a and 7h were found to be 81.6 and 93.1 µg/mL, respectively, against the bacterium Ralstonia solanacearum (Rs), being over twofold more active than commercial agrobactericide Thiodiazole-copper (189.6 µg/mL). Finally, some compounds displayed a certain degree of inhibition activity against tested phytopathogenic fungi at 50 µg/mL.
基于药效团杂合方法,设计并合成了一系列结构新颖的 3-硫醚-1-(喹唑啉-4-基)-1H-1,2,4-三唑-5-胺衍生物(7a-7r),并对其进行了体外抗菌和抗真菌活性筛选。所有目标化合物均通过 [Formula: see text]H NMR、[Formula: see text]C NMR 和 HRMS 谱进行了充分表征。其中,化合物 7b 的结构通过单晶 X 射线衍射分析进一步证实。结果表明,采用浊度法,部分目标化合物对测试的植物病原菌表现出显著的抑制活性。例如,化合物 7d、7g 和 7i 对柑橘溃疡病菌(Xac)的 EC[Formula: see text](半最大有效浓度)值分别为 46.9、47.8 和 43.2 µg/mL,优于商品化杀细菌剂双噻唑锌(56.9 µg/mL)。此外,化合物 7a 和 7h 对青枯病菌(Rs)的 EC[Formula: see text]值分别为 81.6 和 93.1 µg/mL,活性优于商品化杀细菌剂噻菌铜(189.6 µg/mL),是其两倍多。最后,一些化合物在 50 µg/mL 时对测试的植物病原菌真菌显示出一定的抑制活性。