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设计和合成小分子 2-氨基苯并恶唑类化合物作为潜在的抗植物病原真菌的杀菌剂。

Design and synthesis of small molecular 2-aminobenzoxazoles as potential antifungal agents against phytopathogenic fungi.

机构信息

State Key Laboratory of Functions and Applications of Medicinal Plants and College of Pharmacy, Guizhou Provincial Engineering Technology Research Center for Chemical Drug R&D, Guizhou Provincial Key Laboratory of Pathogenesis and Drug Research on Common Chronic Diseases, Guizhou Medical University, Guiyang, 550004, People's Republic of China.

Key Laboratory of Green Pesticide and Agricultural Bioengineering, Ministry of Education, Guizhou University, Guiyang, 550025, People's Republic of China.

出版信息

Mol Divers. 2022 Apr;26(2):981-992. doi: 10.1007/s11030-021-10213-7. Epub 2021 Apr 3.

DOI:10.1007/s11030-021-10213-7
PMID:33811571
原文链接:https://pmc.ncbi.nlm.nih.gov/articles/PMC8019306/
Abstract

In order to discover novel antifungal agents, three series of simple 2-aminobenzoxazole derivatives were designed, synthesized and evaluated for their antifungal activities against eight phytopathogenic fungi. The in vitro antifungal results showed that most of the target compounds exhibited excellent and broad-spectrum antifungal activities to all the tested fungi. Particularly, the six compounds 3a, 3b, 3c, 3e, 3m and 3v displayed the most potent antifungal activity, with EC value of 1.48-16.6 µg/mL, which were much superior to the positive control hymexazol. The in vivo study further confirmed that compounds 3a, 3c, 3e and 3m displayed good preventative effect against Botrytis cinerea at the concentration of 100 µg/mL. The structure-activity relationships research provides significant reference for the further structural optimization of 2-aminobenzoxazole as potential fungicides. Forty-four 2-aminobenzoxazole derivatives were designed and synthesized as agricultural antifungal agents, the in vitro and in vivo antifungal experiments showed that compounds 3a, 3b, 3c, 3e, 3m and 3v exhibited excellent and broad-spectrum antifungal activities compare with the commercial fungicide hymexazol.

摘要

为了发现新型抗真菌剂，设计、合成了三个系列的简单 2-氨基苯并恶唑衍生物，并评估了它们对 8 种植物病原真菌的抗真菌活性。体外抗真菌结果表明，大多数目标化合物对所有测试的真菌均表现出优异和广谱的抗真菌活性。特别是化合物 3a、3b、3c、3e、3m 和 3v 表现出最强的抗真菌活性，EC 值为 1.48-16.6µg/mL，优于阳性对照 hymexazol。体内研究进一步证实，化合物 3a、3c、3e 和 3m 在 100µg/mL 浓度下对灰葡萄孢具有良好的预防作用。构效关系研究为进一步对 2-氨基苯并恶唑进行结构优化作为潜在的杀菌剂提供了重要参考。设计并合成了 44 种 2-氨基苯并恶唑衍生物作为农用抗真菌剂，体外和体内抗真菌实验表明，化合物 3a、3b、3c、3e、3m 和 3v 与商品化杀菌剂 hymexazol 相比，表现出优异和广谱的抗真菌活性。

https://cdn.ncbi.nlm.nih.gov/pmc/blobs/e15a/8019306/eb61518d9d1e/11030_2021_10213_Fig6_HTML.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/e15a/8019306/856fff2b9767/11030_2021_10213_Fig1_HTML.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/e15a/8019306/a22e9b36a1f9/11030_2021_10213_Sch1_HTML.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/e15a/8019306/5571dd435f86/11030_2021_10213_Fig2_HTML.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/e15a/8019306/f8eff11312e2/11030_2021_10213_Fig3_HTML.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/e15a/8019306/97873c82a464/11030_2021_10213_Fig4_HTML.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/e15a/8019306/fb030555ccd5/11030_2021_10213_Fig5_HTML.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/e15a/8019306/eb61518d9d1e/11030_2021_10213_Fig6_HTML.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/e15a/8019306/856fff2b9767/11030_2021_10213_Fig1_HTML.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/e15a/8019306/a22e9b36a1f9/11030_2021_10213_Sch1_HTML.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/e15a/8019306/5571dd435f86/11030_2021_10213_Fig2_HTML.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/e15a/8019306/f8eff11312e2/11030_2021_10213_Fig3_HTML.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/e15a/8019306/97873c82a464/11030_2021_10213_Fig4_HTML.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/e15a/8019306/fb030555ccd5/11030_2021_10213_Fig5_HTML.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/e15a/8019306/eb61518d9d1e/11030_2021_10213_Fig6_HTML.jpg

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