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Diversity-oriented synthesis and antifungal activities of novel pimprinine derivative bearing a 1,3,4-oxadiazole-5-thioether moiety

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Abstract

Based on the strategy of diversity-oriented synthesis and the structures of natural product pimprinine and streptochlorin, two series of novel pimprinine derivatives containing 1,3,4-oxadiazole-5-thioether moieties were efficiently synthesized under the optimized reaction conditions. Biological assays conducted at Syngenta showed the designed derivatives displayed an altered pattern of biological activity, of which 5h was identified as the most promising compound with strong activity against Pythium dissimile and also a broad antifungal spectrum in primary screening. Further structural optimization of pimprinine and streptochlorin derivatives is well under way, aiming to discover synthetic analogues with improved antifungal activity.

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Two series of novel pimprinine derivatives containing 1,3,4-oxadiazole-5-thioether moieties were efficiently synthesized through diversity-oriented synthesis strategy under the optimized conditions. Biological assays showed the designed derivatives exhibited potential activity.

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Acknowledgements

We are grateful to the financial support for this work from the National Natural Science Foundation of China (21602110), National Key R&D Program of China (2018YFC1602804), Jiangsu Provincial Science Foundation for Youths (BK20160734) and the Fundamental Research Funds and for the Central Universities (KYTZ201604, KYLH201908). We thank the Biology Team at Syngenta for their kind help in screening the compounds for biological activity.

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Authors and Affiliations

  1. Jiangsu Key Laboratory of Pesticide Science, College of Sciences, Nanjing Agricultural University, Nanjing, 210095, China

    Zi-Long Song, Yun Zhu, Jing-Rui Liu, Shu-Ke Guo, Wei-Hua Zhang & Ming-Zhi Zhang

  2. Syngenta Jealott’s Hill International Research Centre, Bracknell, Berkshire, RG42 6EY, UK

    Yu-Cheng Gu

  3. School of Chemistry and Chemical Engineering, Anhui University of Technology, Ma’anshan, 243002, China

    Xinya Han

  4. College of Plant Science, Tarim University, Alaer, 843300, Xinjiang, China

    Hong-Qiang Dong

  5. Key Laboratory for Green Chemical Process of Ministry of Education, School of Chemistry and Environmental Engineering, Wuhan Institute of Technology, Wuhan, 430205, China

    Qi Sun

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Song, ZL., Zhu, Y., Liu, JR. et al. Diversity-oriented synthesis and antifungal activities of novel pimprinine derivative bearing a 1,3,4-oxadiazole-5-thioether moiety. Mol Divers 25, 205–221 (2021). https://doi.org/10.1007/s11030-020-10048-8

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