Synthesis, Biological Evaluation, and Structure–Activity Relationship Study of Novel Stilbene Derivatives as Potential Fungicidal Agents

He, Daohang; Jian, Weilin; Liu, Xianping; Shen, Huolin; Song, Shuang

doi:10.1021/jf5052893

Cited by 26 publications

(34 citation statements)

References 34 publications

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“…Inner vacuoles were found in 5j ‐treated hyphae, whereas this was rarely seen in the control mycelium. Similar results were observed in our previous study in which the mycelial cell membrane system was significantly damaged by the membrane permeability assay …”

Section: Resultssupporting

confidence: 92%

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Synthesis and antifungal activities of novel thiophene‐based stilbene derivatives bearing an 1,3,4‐oxadiazole unit

Wen

Jian

Shang

et al. 2018

Pest Management Science

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BACKGROUND Natural stilbenes (especially resveratrol and its derivatives) are well‐known phytoalexins that are active against many plant diseases. However, oxidative degradation and low bioavailability limit their exogenous application as fungicides on crops. In this study, a new class of resveratrol‐inspired thiophene‐based stilbene derivatives bearing an 1,3,4‐oxadiazole unit was synthesized and the derivatives' antifungal activities against phytopathogenic fungi were investigated. RESULTS The results revealed that compounds 5h and 5j exhibited improved antifungal activity against Botrytis cinerea with median effective concentrations (EC50) of 168.5 and 155.4 µg mL−1, respectively, which were superior to the EC50 of resveratrol (263.1 µg mL−1). Compound 5j was shown to effectively control disease development in B. cinerea‐infected tomatoes in vivo. Notably, considerably abnormal mycelial morphology and increased cell membrane conductivity were observed in the presence of compound 5j. CONCLUSION A new class of thiophene‐containing stilbene derivatives was designed and synthesized. Bioassay results showed that compound 5j exhibited promising antifungal activity, suggesting practical potential for fungal disease control. © 2018 Society of Chemical Industry

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Section: Resultssupporting

confidence: 92%

“…Similar results were observed in our previous study in which the mycelial cell membrane system was significantly damaged by the membrane permeability assay. 17,39…”

Section: Effect On Hyphal Morphology Of B Cinereamentioning

confidence: 99%

Synthesis and antifungal activities of novel thiophene‐based stilbene derivatives bearing an 1,3,4‐oxadiazole unit

Wen

Jian

Shang

et al. 2018

Pest Management Science

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“…14,16 The main objective of adding a terminal styrene moiety to the carborane cluster was to have a suitable group for further functionalization to develop conceptually different light-dependent macromolecules, like dendrimers or octasilsesquioxanes, 17,18 as well as small fluorescent molecules. 16 Due to the interest generated by the application of stilbene derivatives [19][20][21] in fields such as biomedicine, [22][23][24][25] electro-optic materials, 26 LEDs, 27 non-linear optics 28 among others; we aimed to develop new carborane-stilbene compounds from our previous styrene derivatives to study the influence of the C c -substituted cluster on their photophysical properties. In a previous work, we synthesized stilbene-carborane triads in which o-or m-carborane clusters are linked to two stilbene units through a methylene spacer.…”

Section: Introductionmentioning

confidence: 99%

Carborane–stilbene dyads: the influence of substituents and cluster isomers on photoluminescence properties

et al. 2017

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Two novel styrene-containing meta-carborane derivatives substituted at the second carbon cluster atom (C) with either a methyl (Me) or a phenyl (Ph) group are introduced herein along with a new set of stilbene-containing ortho- (o-) and meta- (m-) carborane dyads. The latter set of compounds have been prepared from styrene-containing carborane derivatives via a Heck coupling reaction. High regioselectivity has been achieved for these compounds by using a combination of palladium complexes [Pd(dba)]/[Pd(t-BuP)] as a catalytic system, yielding exclusively E isomers. All compounds have been fully characterised and the crystal structures of seven of them were analysed by X-ray diffraction. The absorption spectra of these compounds are similar to those of their respective fluorophore groups (styrene or stilbene), showing a very small influence of the substituent (Me or Ph) linked to the second C atom or the cluster isomer (o- or m-). On the other hand, fluorescence spectroscopy revealed high emission intensities for Me-o-carborane derivatives, whereas their Ph-o-carborane analogues evidenced an almost total lack of fluorescence, confirming the significant role of the substituent bound to the adjacent C in o-carboranes. In contrast, all the m-carborane derivatives display similar photoluminescence (PL) behavior regardless of the substituent attached to the second C, demonstrating its small influence on emission properties. Additionally, m-carborane derivatives are significantly more fluorescent than their o-counterparts, reaching quantum yield values as high as 30.2%. Regarding solid state emission, only stilbene-containing Ph-o-carborane derivatives, which showed very low fluorescence in solution, exhibited notable PL emission in films attributed to aggregation-induced emission. DFT calculations were performed to successfully complement the photoluminescence studies, supporting the experimentally observed photophysical behavior of the styrene and stilbene-containing carborane derivatives. In conclusion, in this work it is proved that it is possible to tailor the PL properties of carborane-stilbene dyads by changing the C substituent and the carborane isomer.

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“…The antimicrobial activity is linked to the presence of strongly electron-withdrawing substituents on the stilbene skeleton. 29 This may result in the formation of charge transfer complexes, which play an important role in enhancing affinity with the membrane proteins. 30 A decrease in activity has been observed for the electron-rich hydroxylated stilbenes, especially against gram-negative bacteria.…”

Section: Antimicrobial Activitymentioning

confidence: 99%

Synthesis of E -stilbene azomethines as potent antimicrobial and antioxidant agents

Iqbal¹,

Khan²,

Shahzad³

et al. 2018

Turk J Chem

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A series of new extensively conjugated E-stilbene azomethines (5a-5h) were synthesized and screened for their antioxidant and antimicrobial activity. The compounds were tested against bacterial (Escherichia coli, Staphylococcus aureus, Klebsiella pneumoniae, and Bacillus subtilis) and fungal strains (Aspergillus niger, A. flavus, and Trichoderma harzianum) using the agar well diffusion method. Among the tested compounds, N '-(4-nitrobenzylidene)-2-((E)-styryl)benzohydrazide (5g) was found to possess potent antimicrobial activity higher than some drugs with significant activity reported in the literature, e.g., cefradine and terbinafine hydrochloride. Additionally, compounds 5a-5h were also evaluated for antioxidant potential using DPPH free radical scavenging and ferric thiocyanate (FTC) assays. Among these, N '-(4-hydroxybenzylidene)-2-((E)-styryl)benzohydrazide (5e) exhibited significant antioxidant potential by both assays. Compound 5e demonstrated higher DPPH free radical scavenging activity (IC 50 = 22 ± 0.19 µ g/mL) than the standard, butylated hydroxytoluene (BHT; IC 50 = 28 ± 0.10 µ g/mL). A similar trend was observed for compound 5e in FTC assay, which exhibited 86 ± 0.19% inhibition, whereas the BHT control showed 81 ± 0.21% inhibition of linoleic acid peroxidase. The structure elucidation of the synthesized compounds was carried out by UV-Vis, FT-IR, 1 H NMR, 13 C NMR, and elemental analysis and mass spectrometry. These results suggest possible use of these compounds for the rational design of new antimicrobial and antioxidant agents.

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Synthesis, Biological Evaluation, and Structure–Activity Relationship Study of Novel Stilbene Derivatives as Potential Fungicidal Agents

Cited by 26 publications

References 34 publications

Synthesis and antifungal activities of novel thiophene‐based stilbene derivatives bearing an 1,3,4‐oxadiazole unit

Synthesis and antifungal activities of novel thiophene‐based stilbene derivatives bearing an 1,3,4‐oxadiazole unit

Carborane–stilbene dyads: the influence of substituents and cluster isomers on photoluminescence properties

Synthesis of E -stilbene azomethines as potent antimicrobial and antioxidant agents

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