Synthesis and antifungal activity of imidazo[1,2-b]pyridazine derivatives against phytopathogenic fungi

Fan, Lingling; Luo, Zhongfu; Li, Yang; Liu, Xinyun; Fan, Jing; Xue, Wei; Tang, Lei; Li, Yong

doi:10.1016/j.bmcl.2020.127139

Cited by 33 publications

(18 citation statements)

References 22 publications

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“…Currently, the enormous losses to crop yield and quality caused by a variety of phytopathogenic fungi have always been a big issue worldwide during the growth and postharvest of crops [1]. Therefore, chemical synthetic fungicides with great antifungal activity and broad antifungal spectrum have long been extensively employed to manage and control fungal plant diseases to ensure agricultural production [2]. However, the excessive use of commercial fungicides in agriculture has led to the increasing resistance of phytopathogenic fungi to fungicides and side effects, such as toxic residues in food and the potentially harmful effects on the environment [3,4].…”

Section: Introductionmentioning

confidence: 99%

Enhanced antifungal activity of novel cationic chitosan derivative bearing triphenylphosphonium salt via azide-alkyne click reaction

Tan

Zhang

et al. 2020

International Journal of Biological Macromolecules

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Section: Introductionmentioning

confidence: 99%

Enhanced antifungal activity of novel cationic chitosan derivative bearing triphenylphosphonium salt via azide-alkyne click reaction

Tan

Zhang

et al. 2020

International Journal of Biological Macromolecules

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“…On the other hand, the widespread presence of fungi in nature poses a universal threat to plants, animals, and humans. The fungi cause crops yield reduction and induce allergies and respiratory diseases in human [18,19] . Therefore, it is necessary to prepare a green and efficient antifungal agent.…”

Section: Introductionmentioning

confidence: 99%

Synthesis, Crystal Structure, Biological Evaluation and in Silico Studies on Novel (E)‐1‐(Substituted Benzylidene)‐4‐(3‐isopropylphenyl)thiosemicarbazone Derivatives

Fan

Qi²,

Song

et al. 2021

Chemistry & Biodiversity

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A series of (E)‐1‐(substituted benzylidene)‐4‐(3‐isopropylphenyl)thiosemicarbazone derivatives were synthesized and characterized by FT‐IR spectrum, elemental analysis, NMR spectrum, HR‐MS spectrum, and X‐ray single crystal diffraction technology. The crystal structures and packing of (E)‐1‐(4‐fluorobenzylidene)‐4‐(3‐isopropylphenyl)thiosemicarbazone and (E)‐1‐(3‐fluorobenzylidene)‐4‐(3‐isopropylphenyl)thiosemicarbazone were maintained through the intramolecular hydrogen bond (N3‐H6⋅⋅⋅N1) and intermolecular hydrogen bonds (N2‐H4⋅⋅⋅S1, C14‐H14⋅⋅⋅F1 and C7‐H7⋅⋅⋅S1). The results obtained by employing the DPPH free radicals scavenging assay indicated that (E)‐1‐(4‐methoxylbenzylidene)‐4‐(3‐isopropylphenyl)thiosemicarbazone had a more significant antioxidant activity compared with other compounds. The results measured by adopting the disc diffusion method elucidated that (E)‐1‐(4‐trifluoromethylbenzylidene)‐4‐(3‐isopropylphenyl)thiosemicarbazone possessed a more prominent antifungal activity than other compounds. Molecular docking showed that (E)‐1‐(4‐chlorobenzylidene)‐4‐(3‐isopropylphenyl)thiosemicarbazone had the highest affinity with receptor protein (1NMT). Moreover, the drug‐likeness characteristic, physicochemical properties, pharmacokinetic profiles, and bioactivity scores of all the compounds were predicted through in silico studies. The results illustrated that (E)‐1‐(4‐fluorobenzylidene)‐4‐(3‐isopropylphenyl)thiosemicarbazone had the drug‐likeness characteristic and all the compounds were considered as moderately biological active molecules.

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“…Natural products represent a rich source for the discovery and development of novel fungicides either for direct application or structure modification [9] . In continuation of our work on the discovery and development of compounds with superior antifungal activity, [10–14] and in consideration of NBP has the similar structural skeleton to ( Z )‐ligustilide and ( Z )‐butylidenephthalide, herein we selected the natural product of 3‐butylphthalide (NBP) as the lead compound, a series of 6‐substitued NBP derivatives were designed, synthesized and evaluated for their antifungal activities against nine phytopathogenic fungi in vitro .…”

Section: Introductionmentioning

confidence: 99%

Design, Synthesis and Antifungal Activities of 6‐Substituted 3‐Butylphthalide Derivatives against Phytopathogenic Fungi

Luo

et al. 2020

Chemistry & Biodiversity

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In order to discover novel potential antifungal agents, a series of 6-substituted 3-butylphthalide derivatives were designed, synthesized and evaluated for their antifungal activities against nine phytopathogenic fungi. Preliminary bioassay tests showed that five 3-butylphthalide derivatives exhibited more potent antifungal activities than hymexazol at the concentration of 50 μg/mL. Especially, 3-butyl-6-nitro-2-benzofuran-1(3H)-one and 3-butyl-6-hydroxy-5-nitro-2-benzofuran-1(3H)-one had significant fungicidal activity against some phytopathogenic fungi. The EC 50 of 3-butyl-6-nitro-2-benzofuran-1(3H)-one against FS, FO and FG were 6.6, 9.6 and 16.0 μg/mL, respectively. The EC 50 of 3-butyl-6-hydroxy-5-nitro-2-benzofuran-1(3H)-one against BC, PO, VM, SS and AS were 6.3, 5.9, 10.0, 4.5 and 8.4 μg/mL, respectively. The preliminary structure-activity relationships (SARs) of all target compounds were also investigated.

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Synthesis and antifungal activity of imidazo[1,2-b]pyridazine derivatives against phytopathogenic fungi

Cited by 33 publications

References 22 publications

Enhanced antifungal activity of novel cationic chitosan derivative bearing triphenylphosphonium salt via azide-alkyne click reaction

Enhanced antifungal activity of novel cationic chitosan derivative bearing triphenylphosphonium salt via azide-alkyne click reaction

Synthesis, Crystal Structure, Biological Evaluation and in Silico Studies on Novel (E)‐1‐(Substituted Benzylidene)‐4‐(3‐isopropylphenyl)thiosemicarbazone Derivatives

Design, Synthesis and Antifungal Activities of 6‐Substituted 3‐Butylphthalide Derivatives against Phytopathogenic Fungi

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