Synthesis and biological activity of novel Pyrazolo[3,4‐d]pyrimidin‐4‐one derivatives as potent antifungal agent

Wang, Wei; Cheng, Xiang; Cui, Xue; Xia, Dong-Guo; Wang, Ziqing; Lv, Xian-Hai

doi:10.1002/ps.6406

Cited by 14 publications

(12 citation statements)

References 20 publications

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“…mali, and S. sclerotiorum at a concentration of 20 mg/L for the preliminary screening according to the mycelia growth inhibition method. , The detailed experimental method is given in the Supporting information.…”

Section: Materials and Methodsmentioning

confidence: 99%

Rational Design, Synthesis, and Biological Evaluation of Fluorine- and Chlorine-Substituted Pyrazol-5-yl-benzamide Derivatives as Potential Succinate Dehydrogenase Inhibitors

Wang

et al. 2022

J. Agric. Food Chem.

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To develop novel succinate dehydrogenase inhibitors (SDHIs), two series of novel N-4-fluoro-pyrazol-5-ylbenzamide and N-4-chloro-pyrazol-5-yl-benzamide derivatives were designed and synthesized, and their antifungal activities were evaluated against Valsa mali, Sclerotinia sclerotiorum, FusaHum graminearum Sehw, Physalospora piricola, and Botrytis cinerea. The bioassay results showed that some of the target compounds exhibited good antifungal activities in vitro against V. mali and S. sclerotiorum. Remarkably, compound 9Ip displayed good in vitro activity against V. mali with an EC 50 value of 0.58 mg/L. This outcome was 21-fold greater than that of fluxapyroxad (12.45 mg/L) and close to that of the commercial fungicide tebuconazole (EC 50 = 0.36 mg/L). In addition, in vivo experiments proved that compound 9Ip has good protective fungicidal activity with an inhibitory rate of 93.2% against V. mali at 50 mg/L, which was equivalent to that of the positive control tebuconazole (95.5%). The results of molecular docking indicated that there were obvious hydrogen bonds and p−π interactions between compound 9Ip and succinate dehydrogenase (SDH), which could explain the probable action mechanism. In addition, the SDH enzymatic inhibition assay was carried out to further prove its mode of action. Our studies suggest that compound 9Ip could be a fungicidal lead to discover more potent SDHIs for crop protection.

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Section: Materials and Methodsmentioning

confidence: 99%

Rational Design, Synthesis, and Biological Evaluation of Fluorine- and Chlorine-Substituted Pyrazol-5-yl-benzamide Derivatives as Potential Succinate Dehydrogenase Inhibitors

Wang

et al. 2022

J. Agric. Food Chem.

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“…Freshly cultured mycelia were inoculated on PDA plates containing no compound, compounds 3a , 4a , or 5k and incubated at 26 °C, for 7 days, placed on a glass slide and dehydrated [ 29 ]. The morphology of the mycelia was observed by SEM.…”

Section: Methodsmentioning

confidence: 99%

Synthesis, Antifungal Activity, Cytotoxicity and QSAR Study of Camphor Derivatives

Duan

Zhang

et al. 2022

JoF

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Control of fungal phytopathogens affecting crops and woodlands is an important goal in environmental management and the maintenance of food security. This work describes the synthesis of 37 camphor derivatives, of which 27 were new compounds. Their antifungal effects on six fungi were evaluated in vitro. Compounds 3a, 4a and 5k showed strong antifungal activity against Trametes versicolor, with EC50 values of 0.43, 6.80 and 4.86 mg/L, respectively, which were better than that of tricyclazole (EC50 118.20 mg/L) and close to or better than that of carbendazim (EC50 1.20 mg/L). The most potent compound, 3a, exhibited broad-spectrum antifungal activity towards six fungi with EC50 values within the range of 0.43–40.18 mg/L. Scanning electron microscopy demonstrated that compounds 3a, 4a and 5k gave irregular growth and shriveling of the mycelia. In vitro cytotoxicity evaluation revealed that the tested camphor derivatives had mild or no cytotoxicity for LO2 and HEK293T cell lines. Quantitative structure−activity relationship (QSAR) analysis revealed that the number of F atoms, relative molecular weight, the atomic orbital electronic population and total charge on the positively charged surfaces of the molecules of camphor derivatives have effects on antifungal activity. The present study may provide a theoretical basis for a high-value use of camphor and could be helpful for the development of novel potential antifungals.

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“…The antifungal activities against Botryosphaeria dothidea (B. dothidea), Phompsis sp., Botrytis cinereal (B. cinerea), Colletotrichum gloeosporioides (C. gloeosporioides), Pyricutaria oryzae (P. oryzae), and Sclerotinia sclerotiorum (S. sclerotiorum) of compounds 5a-5w at 50 μg/ml were determined by the typical mycelium growth rate method (Du et al, 2021;Wang W. et al, 2021), and tebuconazole was used as a positive control.…”

Section: In Vitro Antifungal Activity Testmentioning

confidence: 99%

Design, Synthesis, and Bioactivities of Novel Trifluoromethyl Pyrimidine Derivatives Bearing an Amide Moiety

Lan

Tang

et al. 2022

Front. Chem.

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Twenty-three novel trifluoromethyl pyrimidine derivatives containing an amide moiety were designed and synthesized through four-step reactions and evaluated for their antifungal, insecticidal, and anticancer properties. Bioassay results indicated that some of the title compounds exhibited good in vitro antifungal activities against Botryosphaeria dothidea (B. dothidea), Phompsis sp., Botrytis cinereal (B. cinerea), Colletotrichum gloeosporioides (C. gloeosporioides), Pyricutaria oryzae (P. oryzae), and Sclerotinia sclerotiorum (S. sclerotiorum) at 50 μg/ml. Meanwhile, the synthesized compounds showed moderate insecticidal activities against Mythimna separata (M. separata) and Spdoptera frugiperda (S. frugiperda) at 500 μg/ml, which were lower than those of chlorantraniliprole. In addition, the synthesized compounds indicated certain anticancer activities against PC3, K562, Hela, and A549 at 5 μg/ml, which were lower than those of doxorubicin. Notably, this work is the first report on the antifungal, insecticidal, and anticancer activities of trifluoromethyl pyrimidine derivatives bearing an amide moiety.

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Synthesis and biological activity of novel Pyrazolo[3,4‐d]pyrimidin‐4‐one derivatives as potent antifungal agent

Cited by 14 publications

References 20 publications

Rational Design, Synthesis, and Biological Evaluation of Fluorine- and Chlorine-Substituted Pyrazol-5-yl-benzamide Derivatives as Potential Succinate Dehydrogenase Inhibitors

Rational Design, Synthesis, and Biological Evaluation of Fluorine- and Chlorine-Substituted Pyrazol-5-yl-benzamide Derivatives as Potential Succinate Dehydrogenase Inhibitors

Synthesis, Antifungal Activity, Cytotoxicity and QSAR Study of Camphor Derivatives

Design, Synthesis, and Bioactivities of Novel Trifluoromethyl Pyrimidine Derivatives Bearing an Amide Moiety

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