Novel Phosphorylated Penta-1,4-dien-3-one Derivatives: Design, Synthesis, and Biological Activity

Chen, Lijuan; Guo, Tao; Xia, Rongjiao; Xu, Tao; Chen, Ying; Zhang, Cheng; Xue, Wei

doi:10.3390/molecules24050925

Cited by 17 publications

(13 citation statements)

References 35 publications

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“…After 2 to 3 days, obvious spots appear on the leaves, record the number of spots on the left and right sides, and bring them into the formula to calculate the inhibition rate. Each compound is performed 2 to 3 times in parallel …”

Section: Methodsmentioning

confidence: 99%

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Synthesis, Biological Activity and Action Mechanism Study of Novel Chalcone Derivatives Containing Malonate

Guo

Xia

Liu

et al. 2020

Chemistry & Biodiversity

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A series of novel chalcone malonate derivatives were synthesized and their antibacterial and antiviral activities were evaluated. All target compounds were characterized by spectral data. The results of antimicrobial bioassay showed that one compound (diethyl [3-(naphthalen-2-yl)-1-(3-nitrophenyl)-3-oxopropyl]propanedioate) showed excellent antibacterial activity against Xanthomonas oryzae pv. oryzae (Xoo), with an EC 50 value of 10.2 μg/mL, which is significantly superior to bismerthiazol (71.7 μg/mL) and thiodiazole copper (97.8 μg/mL). At the same time, the mechanism of two compounds was confirmed by scanning electron microscopy. In addition, another compound (diethyl [3-(naphthalen-2-yl)-1-(4-nitrophenyl)-3-oxopropyl]propanedioate) showed significant curative activity to tobacco mosaic virus, with a value of 74.3 %, which was superior to 53.3 % of ningnanmycin. The results of microscale thermophoresis also showed that the Kd value of the combination of two compounds with the coat protein of tobacco mosaic virus was 0.211 and 0.166 μmol/L, which was better than 0.596 μmol/L of ningnanmycin. At the same time, the molecular docking of two compounds with tobacco mosaic virus-coat protein shows that the compound is well embedded in the pocket between the two subunits of tobacco mosaic virus-coat protein. These results show that chalcone derivatives containing malonate group can be considered as activators in the design of antibacterial and antiviral agents.

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Section: Methodsmentioning

confidence: 99%

“…Molecule docking study was performed by using DS‐CDoking implemented in Discovery Studio (version 4.5) . First, the target protein molecule PDB file was obtained, which can be searched from the PDB database website.…”

Section: Methodsmentioning

confidence: 99%

Synthesis, Biological Activity and Action Mechanism Study of Novel Chalcone Derivatives Containing Malonate

Guo

Xia

Liu

et al. 2020

Chemistry & Biodiversity

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“…[10] As an important curcumin analogue, penta-1,4-dien-3-ones put up better stability than curcumin, as well as indicating low toxic effects on plants and human health. Penta-1,4-dien-3-ones have contributed greatly to drug discovery over the years, which possess antimicrobial, [19][20][21][22][23][24] antiviral, [25][26][27][28] anticancer, [29][30][31] and anti-inflammatory properties. [32,33] There were various penta-1,4-dien-3-ones derivatives were reported by us recently, and which exhibited remarkable antibacterial activities.…”

Section: Introductionmentioning

confidence: 99%

Synthesis and antibacterial activity of novel 1,4‐pentadien‐3‐one derivatives bearing a benzothiazole moiety

Wang

Zhou

Sun

et al. 2021

Journal of Heterocyclic Chem

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In search of novel and efficient pesticides to combat increasingly resistant plant bacteria, in this work, 17 novel benzothiazole decorated penta-1,4-diene-3-one derivatives were designed and synthesized, the structures of all new compounds were systematically characterized via 1 H-NMR, 13 C-NMR, and HRMS. The results of the bioactivity study indicated that some compounds presented efficient antibacterial activity against Xanthomonas oryzae pv. Oryzae (Xoo) and Xanthomonas axonopodis pv. Citri (Xac). Among them, compounds 3i and 3q exhibited the lowest EC 50 values of 11.9 and 28.5 μg ml À1 toward Xoo and Xac, respectively, both of them did better than those of thiodiazole copper (109.3 and 87.6 μg ml À1 , respectively) and bismerthiazol (73.5 and 55.4 μg ml À1 , respectively). Furthermore, SEM images further validated that the target compound 3i could distinctly make cell membrane destruction of Xoo.

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“…citri (Xac), can severely affect citrus production [6,7]. Bismerthiazol (BT) and thiodiazole copper (TC) are traditional systemic fungicides, which are commonly used to treat rice bacterial leaf blight and citrus canker [8,9]. However, the long-term frequent application of them has led to bactericide-resistant, therefore the phenomenon that rice bacterial leaf blight and citrus canker cannot be effectively controlled has emerged [10].…”

Section: Introductionmentioning

confidence: 99%

Synthesis and Antibacterial Evaluation of Novel 1,3,4-Oxadiazole Derivatives Containing Sulfonate/Carboxylate Moiety

Wang

Zhou

et al. 2020

Molecules

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In order to discover new lead compounds with high antibacterial activity, a series of new derivatives were designed and synthesized by introducing a sulfonate or carboxylate moiety into the 1,3,4-oxadiazole structure. Antibacterial activity against two phytopathogens, Xanthomonas oryzae pv. oryzae (Xoo) and Xanthomonas axonopodis pv. citri (Xac), was assayed in vitro. The preliminary results indicated that ten compounds including 4a-1-4a-4 and 4a-11-4a-16 had good antibacterial activity against Xoo, with EC50 values ranging from 50.1-112.5 µM, which was better than those of Bismerthiazol (253.5 µM) and Thiodiazole copper (467.4 µM). Meanwhile, 4a-1, 4a-2, 4a-3 and 4a-4 demonstrated good inhibitory effect against Xanthomonas axonopodis pv. citri with EC50 values around 95.8-155.2 µM which were better than those of bismerthiazol (274.3 µM) and thiodiazole copper (406.3 µM). In addition, in vivo protection activity of compound 4a-2 and 4a-3 against rice bacterial leaf blight was 68.6% and 62.3%, respectively, which were better than bismerthiazol (49.6%) and thiodiazole copper (42.2%). Curative activity of compound 4a-2 and 4a-3 against rice bacterial leaf blight was 62.3% and 56.0%, which were better than bismerthiazol (42.9%) and thiodiazole copper (36.1%). Through scanning electron microscopy (SEM) analysis, it was observed that compound 4a-2 caused the cell membrane of Xanthomonas oryzae pv. oryzae ruptured or deformed. The present results indicated novel derivatives of 5-phenyl sulfonate methyl 1,3,4-oxadiazole might be potential antibacterial agents.

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Novel Phosphorylated Penta-1,4-dien-3-one Derivatives: Design, Synthesis, and Biological Activity

Cited by 17 publications

References 35 publications

Synthesis, Biological Activity and Action Mechanism Study of Novel Chalcone Derivatives Containing Malonate

Synthesis, Biological Activity and Action Mechanism Study of Novel Chalcone Derivatives Containing Malonate

Synthesis and antibacterial activity of novel 1,4‐pentadien‐3‐one derivatives bearing a benzothiazole moiety

Synthesis and Antibacterial Evaluation of Novel 1,3,4-Oxadiazole Derivatives Containing Sulfonate/Carboxylate Moiety

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