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Synthesis, Antifungal Activity, and QSAR Studies of Benzbutyrolactone Derivatives Based on α-Methylene-γ-butyrolactone Scaffold

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Abstract

α-Methylene-γ-butyrolactone scaffold and benzofuran pharmacophore demonstrate a number of valuable medicinal properties. Based on bioactivity-guided mixed synthesis principle, we have designed and synthesized a series of new derivatives combining these two substructures. Antifungal activity of the products against some pathogenic fungi and cytotoxicity has been tested. QSAR has been performed. All зкщвгсеы demonstrate high activity against B. cinerea and G. graminis. Compounds with the 4-fluorophenyl group and compound connected with the cinnamic aldehyde structure demonstrate superior in vitro and in vivo activity. Results of SARs and QSAR studies exhibit that the lower electron density around the α-methylene-γ-butyrolactone backbone structure and smaller steric hindrance on the exocyclic carbon-carbon double bond are beneficial for antifungal activity. The results indicate benzbutyrolactone derivatives with α-methylene-γ-butyrolactone and benzofuran pharmacophore as highly active low-toxic compounds with the fungicide potential potential.

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Funding

We greatly appreciate the funding support for this research provided by the Natural Science Foundation of Shaanxi Province (no. 2021JQ-842), Shengyong Zhang Academician Project of Shangluo University (no. 18YSZX005) and Introduction of Talent Research Start-up Fund of Shangluo University (no. 18SKY004). We also thank Northwest A&F University for the 1H NMR, 13C NMR, and HR-ESI-MS spectral data.

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Authors and Affiliations

  1. College of Biology Pharmacy and Food Engineering, Shangluo University, Shangluo, 726000, Shaanxi, China

    Yong-Ling Wu, Jin Wei, Yin-Feng Meng & Tian-Tian Yu

  2. Shaanxi Qinling Industrial Technology Research Institute of Special Biological Resources, Shangluo, 726000, Shaanxi, China

    Yong-Ling Wu, Jin Wei & Yin-Feng Meng

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  1. Yong-Ling Wu
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  2. Jin Wei
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Correspondence to Yong-Ling Wu.

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Wu, YL., Wei, J., Meng, YF. et al. Synthesis, Antifungal Activity, and QSAR Studies of Benzbutyrolactone Derivatives Based on α-Methylene-γ-butyrolactone Scaffold. Russ J Gen Chem 92, 1085–1097 (2022). https://doi.org/10.1134/S1070363222060214

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