Design and synthesis of novel 2,2-dimethylchromene derivatives as potential antifungal agents

Li, Yong; Luo, Bilan; Luo, Zhongfu; Ma, Taigui; Fan, Lingling; Liu, Wenjing; Fan, Jing; Guo, Bing; Xue, Wei; Tang, Lei

doi:10.1007/s11030-022-10421-9

Cited by 7 publications

(6 citation statements)

References 33 publications

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“…The antifungal activities of the target compounds were tested by poisoned food technique as the methods reported in our previous work [8,11] . ( Supporting Information )…”

Section: Methodsmentioning

confidence: 99%

“…The antifungal activities of the target compounds were tested by poisoned food technique as the methods reported in our previous work. [8,11] (Supporting Information) tion, Judi fan performed the data analysis, Wei Xue provided the phytopathogenic fungi samples, Lingling Fan, Bing Guo and Lei Tang jointly conceived and supervised this work, Lingling Fan is responsible for manuscript writing.…”

Section: Antifungal Assaymentioning

confidence: 99%

“…Demethoxyencecalin and methylencecalin were isolated from the sunflower receptacle, which displayed antimicrobial activity against bacteria, yeasts and fungi [7] . Furthermore, previous studies of our working group found that glabridin (separated from Glycyrrhiza glabra L.) and its derivatives could be used as a potential antifungal agents, and the structure–activity relationship study showed that 2 H ‐chromene skeleton played a key role in their antifungal potency [8] . Nevertheless, to our best knowledge, the structural modification and antifungal activity of 2 H ‐chromenes were less reported.…”

Section: Introductionmentioning

confidence: 99%

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Natural Products‐Based Fungicides: Synthesis and Antifungal Activity against Plant Pathogens of 2H‐Chromene Derivatives

Liu

Fan

et al. 2022

Chemistry & Biodiversity

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Aiming to search for novel potential antifungal agents, forty 2H‐chromene analogs were designed, synthesized and their antifungal activity against some typical plant pathogenic fungi were firstly evaluated. The in vitro antifungal bioassays showed that some of the target compounds exhibited comparable or better inhibition activities than the commercial agricultural fungicide hymexazol. Especially compound 1m displayed more promising fungicidal effect against Alternaria alternate (EC50=9.9 μg/mL) and Botrytis cinerea (EC50=9.4 μg/mL), which was significantly superior to hymexazol. Moreover, in vivo protective effects results also indicated that compound 1m had an excellent potential for further development as a new botanical pesticide.

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“…The antifungal activities of the target compounds were tested by poisoned food technique as the methods reported in our previous work [8,11] . ( Supporting Information )…”

Section: Methodsmentioning

confidence: 99%

Section: Antifungal Assaymentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

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Natural Products‐Based Fungicides: Synthesis and Antifungal Activity against Plant Pathogens of 2H‐Chromene Derivatives

Liu

Fan

et al. 2022

Chemistry & Biodiversity

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“…These compounds have excellent and broad-spectrum antibacterial, antifungal, antiviral, and insecticidal activities. Additionally, they have pharmacological properties, such as anti-inflammatory, anticancer, and antioxidant activities [ 7 , 8 ].…”

Section: Introductionmentioning

confidence: 99%

“…To the best of our knowledge, 2 H -1-chromene compounds (precocenes I, II, and III), and their regioisomers, which aimed to achieve antifungal activity, have rarely been reported [ 8 , 26 ]. The selective fungitoxic effect of natural chromene, precocene II (6,7-dimethoxy-2,2-dimethyl-2 H -1-chromene), isolated from the volatile fraction of Ageratum hostoIianum plants against the soil-born fungi R. solani and Phytophthra megasperma , triggered the idea behind this article [ 16 ].…”

Section: Introductionmentioning

confidence: 99%

The Synthesis, Fungicidal Activity, and in Silico Study of Alkoxy Analogues of Natural Precocenes I, II, and III

et al. 2022

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This study aimed to synthesize, characterize, and explore the eco-friendly and antifungal potential of precocenes and their derivatives. The organic synthesis of the mono-O-alkyl-2,2-dimethyl 2H-1-chromene series, including the natural product precocene I, and the di-O-alkyl 2,2-dimethyl-2H-1-chromene series, including the natural 2H-1-chromenes precocenes II and III, was achieved. The synthetic compounds were subjected to spectroscopic analysis, 1HNMR,13CNMR, and mass characterization. The antifungal activity of synthesized precocenes I, II, and III, as well as their synthetic intermediates, was evaluated by the poison food technique. Precocene II (EC50 106.8 µg × mL−1 and 4.94 µg mL−1), and its regioisomers 7a (EC50 97.18 µg × mL−1 and 35.30 µg × mL−1) and 7d (EC50 170.58 × µg mL−1), exhibited strong fungitoxic activity against Aspergillus niger and Rhizoctonia solani. Some of the novel chromenes, 11a and 11b, which had never been evaluated before, yielded stronger fungitoxic effects. Finally, docking simulations for compounds with promising fungitoxic activity were subjected to structure–activity relationship analyses against the polygalactouronases and voltage-dependent anion channels. Conclusively, precocenes and their regioisomers demonstrated promising fungitoxic activity; such compounds can be subjected to minor structural modifications to yield promising and novel fungicides.

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Design and Synthesis of Novel Phthalide Derivatives containing 1,3,4‐Oxadiazole/1,2,4‐Triazole Units as Potential Antifungal Agents

Li,

Luo,

Liu

et al. 2024

Chemistry & Biodiversity

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Four series of novel 1,3,4‐oxadiazole/1,2,4‐triazole hybrids of phthalide derivatives were designed and synthesized to search for novel potential antifungal agents. Preliminary antifungal activity assay results showed that compounds 4a, 4b, 4m, 5b, 5f, 5h, and 7h exhibited moderate to excellent inhibitory activity against some phytopathogenic fungi. Among them, compound 5b displayed the most outstanding antifungal effects against V. mali and S. sclerotiorum, with the EC50 mean of 3.96 μg/mL and 5.60 μg/mL, respectively, which was superior to those of commercial fungicides hymexazol and chlorothalonil. Furthermore, compound 5b could completely suppress the spore germination of V. mali at a concentration of 10 μg/mL. Finally, molecular docking revealed that the potential target for the antifungal activity of compound 5b was succinate dehydrogenase (SDH). This research provides novel candidate compounds for the prevention of phytopathogenic fungi.

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Design and synthesis of novel 2,2-dimethylchromene derivatives as potential antifungal agents

Cited by 7 publications

References 33 publications

Natural Products‐Based Fungicides: Synthesis and Antifungal Activity against Plant Pathogens of 2H‐Chromene Derivatives

Natural Products‐Based Fungicides: Synthesis and Antifungal Activity against Plant Pathogens of 2H‐Chromene Derivatives

The Synthesis, Fungicidal Activity, and in Silico Study of Alkoxy Analogues of Natural Precocenes I, II, and III

Design and Synthesis of Novel Phthalide Derivatives containing 1,3,4‐Oxadiazole/1,2,4‐Triazole Units as Potential Antifungal Agents

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