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Synthesis and biological activity of novel Pyrazolo[3,4-d]pyrimidin-4-one derivatives as potent antifungal agent. 2021

Wei Wang, and Xiang Cheng, and Xue Cui, and Dongguo Xia, and Ziqing Wang, and Xianhai Lv
Department of Applied Chemistry, School of Science, Anhui Agricultural University, Hefei, China.

BACKGROUND To promote the discovery and development of new fungicide with novel scaffolds or modes of action, a series of novel 5-(2-chloroethyl)-1-phenyl-6-(pyridin-4-yl)-1,5-dihydro-4H-pyrazolo[3,4-d]pyrimidin-4-one derivatives were synthesized, and evaluated for their antifungal activities. RESULTS The bioassay data showed that compound 8IIId (EC50  = 1.93 mg L-1 ) is superior to boscalid (EC50  = 6.71 mg L-1 ) against Valsa mali. We introduced chiral groups on the structure of 8IIId, and two chiral configurations were respectively synthesized, which are 8Vc and 8Vd. Surprisingly, 8Vc showed significant antifungal activities against Valsa mali and Physalospora piricola with EC50 values of 0.22 and 0.55 mg L-1 . Physiological and biochemical studies showed that the primary action mechanism of compound 8Vc on Valsa mali may involve changing mycelial morphology and increasing cell membrane permeability. CONCLUSIONS These results demonstrated that 8Vc could be further modified as fungicide and provided a valuable reference for antifungal agents with pyrazolo[3,4-d]pyrimidin-4-one skeleton. © 2021 Society of Chemical Industry.

UI MeSH Term Description Entries
D005659 Fungicides, Industrial Chemicals that kill or inhibit the growth of fungi in agricultural applications, on wood, plastics, or other materials, in swimming pools, etc. Industrial Fungicides
D000935 Antifungal Agents Substances that destroy fungi by suppressing their ability to grow or reproduce. They differ from FUNGICIDES, INDUSTRIAL because they defend against fungi present in human or animal tissues. Anti-Fungal Agents,Antifungal Agent,Fungicides, Therapeutic,Antibiotics, Antifungal,Therapeutic Fungicides,Agent, Antifungal,Anti Fungal Agents,Antifungal Antibiotics
D001203 Ascomycota A phylum of fungi which have cross-walls or septa in the mycelium. The perfect state is characterized by the formation of a saclike cell (ascus) containing ascospores. Most pathogenic fungi with a known perfect state belong to this phylum. Ascomycetes,Cochliobolus,Sclerotinia,Ascomycete,Ascomycotas,Sclerotinias
D013329 Structure-Activity Relationship The relationship between the chemical structure of a compound and its biological or pharmacological activity. Compounds are often classed together because they have structural characteristics in common including shape, size, stereochemical arrangement, and distribution of functional groups. Relationship, Structure-Activity,Relationships, Structure-Activity,Structure Activity Relationship,Structure-Activity Relationships

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