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PEST MANAGEMENT SCIENCE · 2025 · IF 3.8

Design and synthesis of novel cinnamamide derivatives-based lansiumamide B as potent fungicidal candidates

Yizhou Yang,Jianrong Tang,Tianrun Zhao,Qi Li,Jiuhui Ye,Jing Zhang,Zhiqing Ma,Xili Liu,Xiaojun Chen,He Yan

BACKGROUND Natural products have been and continue to be a significant resource for developing environmentally friendly pesticides with distinctive structures and mechanisms. Lansiumamide B (LB), a cinnamamide compound extracted from Clausena lansium seeds, has served as the lead compound for the design and synthesis of a series of cinnamamide derivatives. The fungicidal activity of these derivatives has been evaluated. RESULTS The majority of the proposed compounds displayed moderate to considerable antifungal efficacy against the tested pathogenic fungi and oomycetes, with some exhibiting broad-spectrum fungicidal activities. Compound B 26 showed excellent activity against Colletotrichum orbiculare in vitro , with a median effective concentration (EC 50 ) value of 0.36 μg/mL, better than positive control boscalid (0.95 μg/mL) and the lead compound LB (60.18 μg/mL). In vivo , B 26 also exhibited greater fungicidal activity against C. orbiculare than boscalid and LB. Furthermore, the study found that the mycelium cell wall was damaged after treatment with compound B 26 through observation of the mycelial morphology and ultrastructure of C. orbiculare . Consequently, mycelial growth was inhibited. CONCLUSION The results indicated that cinnamamide compounds containing a 1,2,3,4-tetrahydroisoquinoline moiety represent a novel class of antifungal active scaffold, and compound B 26 has the potential to be developed into a new type of fungicide. © 2025 Society of Chemical Industry.

研究领域: 农药化学 · 植物保护 · 天然产物化学
✓ 已验证 DOI PubMed 高影响因子
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Catalysts · 2022 ·Vol. 12 ·期 10 ·1265 · IF 4.501

Highly Efficient Synthesis of Cinnamamides from Methyl Cinnamates and Phenylethylamines Catalyzed by Lipozyme® TL IM under Continuous-Flow Microreactors

Lihua Du,Lingyan Zheng,Yue Pan,Zhikai Sheng,Shiyi Zhang,Hang Lin,Aoying Zhang,Hanjia Xie,Xiping Luo

While a few derivatives of cinnamamides exhibited anti-inflammatory and/ or analgesic activity, in this study, we developed a highly efficient method for the synthesis of cinnamamides from methyl cinnamates and phenylethylamines catalyzed by Lipozyme®TL IM in continuous-flow microreactors. The reaction parameters and broad substrate range of the new method was studied. Maximum conversion (91.3%) was obtained under the optimal condition of substrate molar ratio of 1:2 (methyl 4-chlorocinnamate: phenylethylamine) at 45°Cfor about 40 min. The remarkable features of this work include short residence time, mild reaction conditions, easy control of the reaction process, and that the catalyst can be recycled or reused, which provide a rapid and economical strategy for the synthesis and design of cinnamamide derivatives for further research on drug activity.

研究领域: 有机化学 · 药物化学 · 生物催化
✓ 已验证 DOI 高影响因子
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PROGRESS IN ORGANIC COATINGS · 2024 · IF 6.5

Photopolymerization initiated by p-diethylene glycol monomethyl ether cinnamyl formamide-based disulfide under 455 nm LED with minimized volume shrinkage

Yuhan Zhang,Nan Xiao,Yanjing Gao,Fang Sun

This study introduces a novel p -diethylene glycol monomethyl ether cinnamyl formamide-based disulfide monomer , N,N′ -(disulfanediylbis(2,1-phenylene)) bis(4-(4-(2-(2-methoxyethoxy)ethoxy) phenyl)-2-oxobut-3-enamide) (Mp-BSCF), designed to reduce the volume shrinkage of photosensitive resins and initiate monomer polymerization under 455 nm LED light irradiation. The photochemical properties and photoinitiation efficiency of Mp-BSCF are systematically investigated using UV–vis absorption spectroscopy , electron paramagnetic resonance (EPR) and real-time infrared spectroscopy . Although its weak absorption around 455 nm, Mp-BSCF can generate arylthiyl radicals under 455 nm LED irradiation, and then effectively initiate the polymerization of triethylene glycol dimethacrylate (TEGDMA)/A glycerolate dimethacrylate (Bis-GMA) system. Increasing Mp-BSCF addition enhances the final double bond conversion and maximum polymerization rate of the TEGDMA/Bis-GMA system, reaching up to 82.0 % and 2.02 % s −1 , respectively. Notably, Mp-BSCF significantly reduces the volume shrinkage of the photopolymerization system, with the addition of 10 % Mp-BSCF resulting in a 50 % reduction compared to the control system. This reduction is attributed to the dynamic reversible nature of the S S bond “breaking-recovery” and the intermolecular hydrogen bond interaction. Additionally, Mp-BSCF improves the thermal stability, friction resistance, and hardness of the TEGDMA/Bis-GMA photopolymerization system.

研究领域: 材料科学 · 高分子化学 · 光化学
✓ 已验证 DOI 高影响因子
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JOURNAL OF CHROMATOGRAPHY A · 2024 · IF 3.8

Esterified styrene-maleic acid copolymer modified silica as mixed-mode polymer-brush stationary phases for chromatographic separation

Yibo Yan,Ruilin Yang,Yanan Wang,Yinan Wu,Xiaofei Gu,Xiaoqiang Qiao

Styrene-maleic acid (SMA) copolymer has received much attention for its excellent solubilization characteristics. In this work, SMA copolymer brush-based chromatographic stationary phases were exploited and developed for the first time. First, SMA copolymer brush was in situ grown on the surface of spherical silica via living/controlled reversible addition-fragmentation chain transfer (RAFT) polymerization method. Subsequently, as a proof-of-concept demonstration, the copolymer was esterified by diethylene glycol mono-2-ethylhexyl ether (DGME) and 2-(2-ethylhexyloxy) ethanol (EHOE), respectively. The obtained Sil-SMA-DGME and Sil-SMA-EHOE copolymer-brush chromatographic stationary phases were characterized by transmission electron microscopy, Fourier transform infrared spectrometer, X-ray photoelectron spectroscopy, and thermogravimetric analysis, respectively. The chromatographic retention mechanism indicated that both the two packed columns exhibited hydrophilic/reverse mixed-mode retention modes. The maximum column efficiency was up to 71,000 N/m. The chromatographic separation performance evaluation indicated that the novel kind of stationary phases had excellent separation capabilities for hydrophilic, hydrophobic compounds and phospholipid standards. In addition, by combination with mass spectrometry identification, the Sil-SMA-DGME column was further exploited for separation and identification of phospholipids in human lung cancer cells. Totally, 9 classes including 186 phospholipid species were successfully identified. The results demonstrated the promising application prospects of the novel kind of SMA copolymer-brush chromatographic stationary phases.

研究领域: 分析化学 · 材料科学 · 生物技术
✓ 已验证 产品关联 DOI PubMed 高影响因子
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FIBERS AND POLYMERS · 2023 ·Vol. 24 ·期 5 ·1707-1715 · IF 2.5

Hydrophobically Modified Alginate for Enhancing the Dispersibility of SDS to CuPc Pigment Colorant in Water

Li YunJing,Wang Lei,Wang Rui,Hao Longyun

In this research, sodium alginate (SA) was first oxidized by sodium periodate to convert its 1,2-hydroxyl into aldehyde groups. Then, the cinnamamide was grafted with it through a mild Schiff reaction to get the hydrophobically modified SA (HMSA). The structure of HMSA was determined by FT-IR, 1 H-NMR, and XPS analysis. Subsequently, it was utilized to improve the dispersibility of sodium dodecyl sulfate (SDS) to copper phthalocyanine pigment (CuPc) in aqueous medium. It was found that when the addition amount accounted for 30% of SDS, HMSA could make the dispersion obtain the best settlement stability. In addition, the addition of HMSA could significantly improve the dispersion stability to different pH and temperatures. The results of Turbiscan Stability Index ( TSI ) measurement directly indicated that the TSI index of the CuPc dispersion by SDS/HMSA was lower than that by SDS alone. SDS and HMSA could form an SDS/HMSA composite through hydrophobic interactions or hydrogen bond forces to produce both steric and electric repulsive forces for better stability of CuPc dispersion.

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