Synthesis and Bioactivities of Novel 1,2,4-triazolo[1,5-a]Pyrimidine Derivatives Containing 1,2,4-triazole-5-thione Schiff Base Unit

Abstract

Using 2-benzylthio-5-methyl-7-hydroxyl-1,2,4-triazolo[1,5-a]pyrimidine as starting compound, twenty novel 1,2,4-triazolo[1,5-a]pyrimidine derivatives containing 1,2,4-triazole-5-thione Schiff-base unit were synthesized through sequential reactions of etherification, hydrazinolysis, salification, cyclization and condensation. Target compounds were fully characterized by IR, 1 H NMR, MS techniques and elemental analysis. Preliminary bioassay indicated that some compounds exhibited certain fungicidal or good anti-TMV activities. At the concentration of 500 μg/mL, the inhibition rates of compounds 6b, 6f and 6p against tobacco mosaic virus (TMV) were 41%, 43% and 40%, respectively.

Synthesis and Bioactivities of Novel 1,2,4-Triazolo[1,5-a]pyrimidine Derivatives Containing 7-(1,3,4-Oxadiazolyl)thioether Moiety

“…[1～3] 、除草 [4,5] 、 抗烟草花叶病毒 [6] 和抗癌 [7] 等, 已上市的该类药物有除 草剂磺草唑胺和唑嘧磺草胺等. 1,3,4-噁二唑类杂环化 合物也具有多种生物活性, 如抗菌 [8] 、抗癌…”

“…我们 [6] 前期的研究工作表明: 在 1,2,4-三唑并[1,5-a]嘧啶 骨架的 7-位引入三唑硫酮席夫碱单元后, 部分化合物表 现出较好的抗烟草花叶病毒活性; 而在该骨架的 7-位用 不同的氧乙酰腙 [3] 和不同取代苄氧醚 [18] …”

Synthesis and antibacterial and antiviral activities of myricetin derivatives containing a 1,2,4-triazole Schiff base

“…Similarly, Schiff base compounds have attracted considerable attention because of their unique biological activities, e.g., 1,2,4-triazole Schiff base compounds have both a triazole ring and an imine active fragment of the Schiff base. Therefore, these compounds have a broad spectrum of biological activity such as antibacterial, 21,22 antitumor, 23 antiviral, 24,25 insecticidal, 26 and weeding. 27 Jin et al reported that 1,2,4-triazole Schiff bases could be used to inhibit plant pathogens.…”

Synthesis and Antimicrobial Activity of Novel 2‐Substituted Phenoxy‐N‐(4‐substituted Phenyl‐5‐(1H‐1,2,4‐triazol‐1‐yl)thiazol‐2‐yl)acetamide Derivatives

“…On the other hand, 1,2,4‐triazole derivatives exhibit broad‐spectrum bioactivity and are widely used in agrochemicals and pharmaceuticals . Fungicides containing triazoles, for example, flusilazole, triadimenol, and propiconazole, are the most effective plant protection agents against plant pathogens such as Xanthomonas oryzae pv.…”