Synthesis, Antibacterial Activity, and Mechanisms of Novel 6-Sulfonyl-1,2,4-triazolo[3,4-b][1,3,4]thiadiazole Derivatives

Abstract

A series of novel 6-sulfonyl-1,2,4-triazolo [3,4-b][1,3,4]thiadiazole derivatives were designed and synthesized. CoMFA models were established to analyze the quantitative structure−activity relationships on the basis of the EC 50 values of the compounds. The models were used to design and synthesize compounds 32 and 33 with higher activities. The EC 50 values of compound 33 against Xanthomonas oryzae pv. oryzae (Xoo) and Xanthomonas oryzae pv. oryzicola (Xoc) were 0.59 and 1.63 mg/L, respectively, which were higher than those of thiodiazole copper (90.43 and 97.93 mg/L) and bismerthiazol (68.37 and 75.59 mg/ L). Moreover, protective activities of compound 33 against bacterial leaf streak (BLS) and bacterial leaf blight (BLB) were 49.65% and 49.42%, respectively, which were superior to those of thiodiazole copper (44.28% and 41.51%) and bismerthiazol (38.89% and 40.09%). Protective activity of compound 33 against BLS was closely related to the improvement of defense-related enzyme activities, chlorophyll content, and photosynthesis activation. This is consistent with the upregulated expression of defense responses and photosynthesis-related proteins.

Design and synthesis novel amide derivatives containing an 1,3,4‐oxadiazole moiety as potential antibacterial agents

“…The antibacterial activities in vitro of compounds 1-25 against Xoo and Xoc were determined by the methods reported in previous literatures [3,7]. Compounds were dissolved in DMSO, and the solution was diluted with 0.1% tween 20 to the needed concentration.…”

“…oryzicola ( Xoc ) and Xanthomonas oryzae pv. oryzae ( Xoo ), respectively, which mainly affects the growth of rice in rice, causing rice to reduce production by 20%–50% [2,3]. Rice infected bacterial diseases mainly rely on chemical antibacterial agents to achieve rapid control, thereby reducing production and quality loss [4].…”

Design, synthesis, and bioassay of novel 1‐(3‐chloropyridin‐2‐yl)‐5‐amino‐4‐pyrazole derivatives containing a 1,3,4‐thiadiazole thioether or sulfone moiety

“…Pyrazole and 1,3,4-thiadiazole derivatives are an important class of nitrogen-containing heterocycles with a variety of biological activities (Figure 1) that contain antibacterial [5][6][7][8], anticancer [9,10], antifungal [11][12][13][14][15][16], insecticidal [17], and antiviral [18][19][20] properties and can be applied for active molecular design. In previous work [21,22], we found a series of 1,3,4-oxadiazole sulfide compounds with moderate to excellent antiviral activity.…”

Synthesis and Bioactivities of Novel Galactoside Derivatives Containing 1,3,4-Thiadiazole Moiety

“…It is known that nitrogen-containing heterocyclic compounds have not only a broad spectrum of biological activity and diversity of structure changes but also low toxicity to most warm-blooded animals, birds, fish, and bees ( Mermer et al, 2021 ). 1,3,4-Thiadiazole derivatives, important nitrogen-containing heterocyclic compounds, showed a wide range of bioactivities, such as antifungal ( Bhinge et al, 2015 ; Chudzik et al, 2019 ), antibacterial ( Wu et al, 2021 ), anticancer ( Abas et al, 2021 ; Avvaru et al, 2021 ), and antiviral ( Yu et al, 2017 ) activities. In our previous working, 1,3,4-thiadiazole derivatives of glucosides showed good antibacterial and antifungal activities ( Chen M. et al, 2021 ).…”