JOURNAL OF AGRICULTURAL AND FOOD CHEMISTRY
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2024
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IF 5.7
Bohang Zhou,Juan Fu,Yuhao Zhang,Ruofei Bai,Yiwei Wang,Yiwei Yang,Yingmei Li,Le Zhou
Replacing old pesticides with new pesticide varieties has been the main means to solve pesticide resistance. Therefore, it is necessary to research and develop new antifungal agents for plant protection. In this study, a series of pyridinecarbaldehyde phenylhydrazone derivatives were designed and evaluated for their inhibition activity on plant pathogenic fungi to search for novel fungicide candidates. Picolinaldehyde phenylhydrazone (1) and nicotinaldehyde phenylhydrazone (2) were identified as promising antifungal lead scaffolds. The 4-fluorophenylhydrazone derivatives (1a and 2a) of 1 and 2 showed highly effective and broad-spectrum inhibition activity in vitro on 11 phytopathogenic fungi with EC50 values of 0.870–3.26 μg/mL, superior to the positive control carbendazim in most cases. The presence of the 4-fluorine atom on the phenyl showed a remarkable activity enhancement effect. Compound 1a at 300 μg/mL provided almost complete protection against infection of Alternaria solani on tomatoes over the post-treatment 9 days and high safety to germination of plant seeds. Furthermore, 1a showed strong inhibition activity with an IC50 value of 0.506 μg/mL on succinate dehydrogenase in A. solani. Molecular docking showed that both 1a and 2a can well bind to the ubiquinone-binding region of SDH by the conventional hydrogen bond, carbon–hydrogen bond, π–π or π–amide interaction, π–alkyl interaction, X---F (X = N, C, or H) interaction, and van der Waal forces. Meanwhile, scanning and transmission electron analysis displayed that 1a destroyed the morphology of mycelium and the structure of the cell membrane of A. solani. Fluorescent staining analysis revealed that 1a changed the mitochondrial membrane potential and cell membrane permeability. Thus, pyridinecarbaldehyde phenylhydrazone compounds emerged as novel antifungal lead scaffolds, and 1a and 2a can be considered promising candidates for the development of new agricultural fungicides.
研究领域:
植物病理学
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分子生物学
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农业化学
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植物保护
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DOI
PubMed
高影响因子
MOLECULES
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2016
·Vol. 21
·期 11
·1574
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IF 2.465
Xing Wang,Yong-Fei Chen,Wei Yan,Ling-Ling Cao,Yong-Hao Ye
A series of benzimidazole phenylhydrazone derivatives (6a–6ai) were synthesized and characterized by1H-NMR, ESI-MS, and elemental analysis. The structure of6bwas further confirmed by single crystal X-ray diffraction as (E)-configuration. All the compounds were screened for antifungal activity againstRhizoctonia solaniandMagnaporthe oryzaeemploying a mycelium growth rate method. Compound6fexhibited significant inhibitory activity againstR. solaniandM. oryzaewith the EC50values of 1.20 and 1.85 μg/mL, respectively. In vivo testing demonstrated that6fcould effectively control the development of rice sheath blight (RSB) and rice blast (RB) caused by the above two phytopathogens. This work indicated that the compound6fwith a benzimidazole phenylhydrazone scaffold could be considered as a leading structure for the development of novel fungicides.Keywords:benzimidazole;phenylhydrazone;antifungal activity
研究领域:
植物病理学
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药物化学
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DOI
PubMed
高影响因子
JOURNAL OF CHEMICAL THERMODYNAMICS
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2019
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IF 2.29
Yanyan Zhou,Jiaxin Wu,Ali Farajtabar,Jian Wang,Hongkun Zhao
Investigation upon the solubility of monobenzone in aqueous co-solvent mixtures of isopropanol, n -propanol, ethylene glycol (EG) and ethanol was performed via a saturation shake-flask technique at temperatures from 283.15 K to 328.15 K under pressure of p = 101.2 kPa. Experimental solubility magnitude presented positive dependence upon the mass fraction of each co-solvent and temperature. The greatest solubility value on the mole fraction scale was observed in the neat co-solvents. The equilibrated solids with corresponding co-solvent mixtures were characterized through an X -ray power diffraction (XRD) technique, demonstrating the absence of polymorphic transformation or solvate formation. The Jouyban-Acree model was adopted to mathematically describe the monobenzone solubility data. The maximum magnitudes of RAD and RMSD were 3.17 × 10 −2 and 7.64 × 10 −4 , respectively. The local mole fractions of isopropanol ( n -propanol, EG or ethanol) and water adjacent monobenzone were quantitatively studied by the Inverse Kirkwood–Buff integrals method. The parameters of preferential solvation for the isopropanol ( n -propanol, EG or ethanol) were positive in the isopropanol ( n -propanol, EG or ethanol) mixtures in intermediate and alcohol-rich compositions, indicating that monobenzone was preferentially solvated by the isopropanol ( n -propanol, EG or ethanol). Monobenzone mainly acted as a Lewis acid which interacted with proton-acceptor functional group of the alcohols. Furthermore, the analysis of linear solvation energy relationships was made with a suitable combination of the solvent polarity descriptors to reveal the nature of intermolecular interactions bringing about the solubility variation in the co-solvent mixtures.
研究领域:
化学工程
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物理化学
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DOI
高影响因子
Journal of the Taiwan Institute of Chemical Engineers
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2021
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IF 5.876
Liu Yang,Yu-Long Liu,Xian-Xian Ji,Cheng-Guo Liu,Ying Fu,Fei Ye
Background A novel luminescent sensor with dual-emitting platforms, Tb@UiO-66 , was used for highly detecting Sm 3+ and teflubenzuron. Methods Tb@UiO-66 was synthesized on basis of the exchange of guest molecules, where Tb 3+ ions were encapsulated into the cages of UiO-66 . Significant finds The results of multiband fluorescence originated from the linker-to-cluster charge transfer and the characteristic emission of Tb III . Tb@UiO-66 displayed luminescence enhancements or quenches according to small molecules. Especially for Sm 3+ and teflubenzuron, the characteristic peaks of Tb@UiO-66 at 490, 545, 585, and 621 nm increased with the increasing of the concentration of the analytes, where Tb@UiO-66 exhibited the effect of luminescence enhancement. The detection limits for detecting Sm 3+ and teflubenzuron were 0.09 μM and 0.21 μM, and the changes of luminescence intensities could be observed by naked eyes under the UV light at 365 nm. Tb@UiO-66 could also be used to detect teflubenzuron in real water samples. Tb@UiO-66 could be reused for at least 5 cycles for the detection of Sm 3+ and teflubenzuron with the framework of Tb@UiO-66 uncollapsed. These results implied that the integration of Ln III luminescent materials and Zr-MOFs by doping method provided a new strategy for fabricating novel luminescent sensors for detecting polluting small molecules.
研究领域:
材料科学
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环境科学
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分析化学
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产品关联
DOI
高影响因子
JOURNAL OF CHROMATOGRAPHY A
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2016
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IF 3.926
Desheng Hou,Jingjing Fan,Lingfei Han,Xiaoling Ruan,Feng Feng,Wenyuan Liu,Feng Zheng
A method for the determination of small halogenated carboxylic acid (HCA) residues in drug substances is urgently needed because of the potential of HCAs for genotoxicity and carcinogenicity in humans. We have now developed a simple method, involving derivatization followed by high performance liquid chromatography-diode array detection (HPLC-DAD), for the determination of six likely residual HCAs (monochloroacetic acid, monobromoacetic acid, dichloroacetic acid, 2-chloropropionic acid, 2-bromopropionic acid and 3-chloropropionic acid) in drug substances. Different nitro-substituted phenylhydrazines (NPHs) derivatization reagents were systematically compared and evaluated. 2-Nitrophenylhydrazine hydrochloride (2-NPH·HCl) was selected as the most suitable choice since its derivatives absorb strongly at 392 nm, a region of the spectrum where most drug substances and impurities absorb very weakly. During the derivatization process, the commonly used catalyst, pyridine, caused rapid dechlorination or chlorine substitution of α-halogenated derivatives. To avoid these unwanted side reactions, a reliable derivatization method that did not use pyridine was developed. Reaction with 2-NPH·HCl using 1-ethyl-3-(3-dimethylaminopropyl) carbodiimide hydrochloride as coupling agent in acetonitrile-water (70:30) at room temperature for 2 h gave complete reaction and avoided degradation products. The derivatives were analyzed, without any pretreatment, using gradient HPLC with detection in the near visible region. Organic acids commonly found in drug substances and other impurities did not interfere with the analysis. Good linearity ( r > 0.999) and low limits of quantitation (0.05–0.12 μg mL −1 ) were obtained. The mean recoveries were in the range of 80–115% with RSD <5.81% except for 3-CPA in ibuprofen which was 78.5%. The intra- and inter-day precisons were expressed as RSD <1.98% and <4.39%, respectively. Finally, the proposed method was successfully used for the residue determination of the six HCAs in eight drug substance samples.
研究领域:
分析化学
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药学
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DOI
PubMed
高影响因子
Marine Drugs
·
2022
·Vol. 20
·期 7
·449
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IF 6.085
Wei Liu,Liang Ma,Liping Zhang,Yuchan Chen,Qingbo Zhang,Haibo Zhang,Weimin Zhang,Changsheng Zhang,Wenjun Zhang
Two new phenylhydrazone derivatives and one new alkaloid, penzonemycins A–B (1–2) and demethylmycemycin A (3), together with three known compounds including an alkaloid (4) and two sesquiterpenoids (5–6), were isolated from theStreptomycessp. SCSIO 40020 obtained from the Pearl River Estuary sediment. Their structures and absolute configurations were assigned by 1D/2D NMR, mass spectroscopy and X-ray crystallography. Compound1was evaluated in four human cancer cell lines by the SRB method and displayed weak cytotoxicity in three cancer cell lines, with IC50values that ranged from 30.44 to 61.92 µM, which were comparable to those of the positive control cisplatin. Bioinformatic analysis of the putative biosynthetic gene cluster indicated a Japp–Klingemann coupling reaction involved in the hydrazone formation of1and2.Keywords:penzonemycins;phenylhydrazones;Streptomycessp.;Japp–Klingemann coupling reaction;marine natural products
研究领域:
海洋化学
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药物化学
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微生物学
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生物化学
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癌症研究
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产品关联
DOI
PubMed
高影响因子
危险品化学品经营许可证（带存储）