Synthesis, antifungal activity and mechanism of action of novel chalcone derivatives containing 1,2,4-triazolo-[3,4-b]-1,3,4-thiadiazole

Zhan, Wenliang; Zhou, Ran; Mao, Piao; Yuan, Chunmei; Zhang, Tao; Liu, Yi; Tian, Jiao; Wang, Hua; Xue, Wei

doi:10.1007/s11030-022-10593-4

Cited by 10 publications

(1 citation statement)

References 41 publications

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“…Thiadiazoles and their derivatives are increasingly used as fungicides worldwide [1,2]. Etridiazole (5-ethoxy-3-trichloromethyl-1,2,4-thiadiazole; EDZ) is a thiadiazole fungicide applied to control Pythium and Phytophthora spp.…”

Section: Introductionmentioning

confidence: 99%

Transcriptome Profiling of Etridiazole-Exposed Zebrafish (Danio rerio) Embryos Reveals Pathways Associated with Cardiac and Ocular Toxicities

Vasamsetti,

Chon,

Yoon

et al. 2023

IJMS

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Etridiazole (EDZ) is a thiadiazole-containing fungicide commonly used to control Pythium and Phytophthora spp. Although previous studies have shown that EDZ is teratogenic, the exact molecular mechanisms underlying its toxicity remain unknown. In this study, a zebrafish (Danio rerio; ZF) model was used to explore the molecular pathways associated with EDZ toxicity. The whole transcriptome of ZF embryos exposed to 96 h of EDZ was analyzed, along with developmental abnormalities. EDZ-induced malformations were primarily related to the eyes, heart, and growth of the ZF. Compared to untreated ZF, etridiazole-treated ZF had 2882 differentially expressed genes (DEGs), consisting of 1651 downregulated genes and 1231 upregulated genes. Gene ontology enrichment analysis showed that DEGs were involved in biological processes, such as sensory perception, visual perception, sensory organ development, and visual system development, and showed transmembrane transporter and peptidase regulator activities. Metabolism, phototransduction, aminoacyl-tRNA biosynthesis, MAPK signaling pathway, calcium signaling pathway, and vascular smooth muscle contraction were among the most enriched KEGG pathways. The qPCR analyses of the eight random genes were in good agreement with the transcriptome data. These results suggest several putative mechanisms underlying EDZ-induced developmental deformities in ZF.

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Section: Introductionmentioning

confidence: 99%

Transcriptome Profiling of Etridiazole-Exposed Zebrafish (Danio rerio) Embryos Reveals Pathways Associated with Cardiac and Ocular Toxicities

Vasamsetti,

Chon,

Yoon

et al. 2023

IJMS

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Methoxy Chalcone Derivatives: Promising Antimicrobial Agents Against Phytopathogens

Santos,

Sousa Ferreira,

Barreto Alves

et al. 2024

Chemistry & Biodiversity

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Chalcone (E)‐1,3‐diphenyl‐prop‐2‐en‐1‐one and a series of 14 methoxylated derivatives have been synthesized via Claisen–Schmidt aldol condensation and characterized by FTIR, CG/MS/DIC, 1D (1H and 13C), 2D (COSY, HSQC, and HMBC) NMR, and EMAR techniques. All molecules were tested at 1mM concentration for antifungal (Sclerotium sp., Macrophomina phaesolina and Colletotrichum gloeosporioides), antibacterial (Acidovorax citrulli two strains), and antiprotozoal (Phytomonas serpens) activities. Unmodified chalcone (CH0) and derivatives CH1, CH2, CH8 stood out in terms of antifungal activity. CH0 presented IC50 values of 47.3 µM (9.8 µg/mL) for the fungus C. gloeosporioides. In addition, fluorescence microscopy indicated that CH0 promoted loss of hyphal cell membrane integrity. The CH1 and CH2 derivatives promoted the inhibition of Sclerotium sp. with IC50 of 127.5 µM (32.9 µg/mL) and 110.4 µM (29.6 µg/mL), respectively. All molecules showed high activity against the phytoparasite P. serpens with IC50 values of 0.98, 2.40, 10.25, and 3.11 µM for the derivatives CH2, CH3, CH5 and CH14 respectively. The results demonstrated that derivatives methoxylated in both rings (CH2) as well as derivatives with a furan ring associated with the methoxy group in ring A, as well as unmodified chalcone can be promising agricultural fungicides for controlling the fungi studied.

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Antifungal activity of chalcone derivatives containing 1,2,3,4‐tetrahydroquinoline and studies on them as potential SDH inhibitors

Deng,

Xin,

Luo

et al. 2024

Pest Management Science

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BackgroundA large number of pathogenic fungi have caused serious damage to the global crop yield, and drug resistance is always a topic that cannot be avoided for traditional fungicides. Therefore, finding efficient, green, and low‐toxic fungicides is our primary task, which brings opportunities for the development of natural product green pesticides.ResultsTwenty chalcone derivatives containing 1,2,3,4‐tetrahydroquinoline were designed and synthesized, and the compounds were tested for their fungicidal effects against eight plant pathogenic fungi in vitro. The results demonstrate that the original splicing did not have fungicidal activity, so a piperazine fragment was introduced; the test results revealed that H1–H10 all had good antifungal activity. Among them, H4 showed the highest inhibitory activity against Phytophthora capsici (Pc) with a median effect concentration (EC50) value of 5.2 μg/mL, which was higher than that of the control drugs Azoxystrobin (EC50 = 80.2 μg/mL) and Fluopyram (EC50 = 146.8 μg/mL). After the study, it was demonstrated that H4 mainly acted on the cell membrane against Phytophthora capsici and inhibited the activity of the marker enzyme of mitochondria (SDH) in the fungus.ConclusionH4 has significant resistance to Phytophthora capsici and also plays a significant role in inhibiting SDH activity, providing a new direction for the development of green pesticides. © 2024 Society of Chemical Industry.

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Synthesis, antifungal activity and mechanism of action of novel chalcone derivatives containing 1,2,4-triazolo-[3,4-b]-1,3,4-thiadiazole

Cited by 10 publications

References 41 publications

Transcriptome Profiling of Etridiazole-Exposed Zebrafish (Danio rerio) Embryos Reveals Pathways Associated with Cardiac and Ocular Toxicities

Transcriptome Profiling of Etridiazole-Exposed Zebrafish (Danio rerio) Embryos Reveals Pathways Associated with Cardiac and Ocular Toxicities

Methoxy Chalcone Derivatives: Promising Antimicrobial Agents Against Phytopathogens

Antifungal activity of chalcone derivatives containing 1,2,3,4‐tetrahydroquinoline and studies on them as potential SDH inhibitors

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