Synthesis and biological activity of novel Pyrazolo[3, 4‐d]pyrimidin‐4‐one derivatives as potent antifungal agent. Issue 7 (12th May 2021)

• Record Type: Journal Article
• Authors: Wang, Wei; Cheng, Xiang; Cui, Xue; Xia, Dongguo; Wang, Ziqing; Lv, Xianhai
• Is Part Of: Pest management science. Volume 77:Issue 7(2021)
• Page Start: 3529
• Page End: 3537
• Publication Date: 2021-05-12
• Subjects: fungicide -- pyrazole -- pyrimidinone -- structure–activity relationships; Pests -- Control -- Periodicals; Pesticides -- Periodicals; 632.9
• DOI: 10.1002/ps.6406
• Languages: English
• ISSNs: 1526-498X

Abstract

Abstract: 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. CONCLUSION: 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. Abstract : Our study indicated 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.