SYNTHESIS-STUTTGART
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2023
·Vol. 55
·期 20
·3393-3401
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IF 2.6
Yue-Lu Zhu,Jie Yan,Xiu-Xuan Xu,Zong-Yu Sun,Jiao Chen
Copper-catalyzed coupling reaction involving N-phenoxyacetamides and 2H-azirines is described, in which N–O and C–N bonds are broken and restructured. This protocol provides an efficient strategy for the highly regioselective synthesis of racemic α-amino oxime ethers. In addition, this strategy can be used to modify natural products and is gram-scale compatible.
研究领域:
有机化学
·
合成化学
✓ 已验证
DOI
高影响因子
MOLECULES
·
2021
·Vol. 26
·期 2
·372
·
IF 4.412
Qing-Qing Wang,Shu-Guang Zhang,Jian Jiao,Peng Dai,Wei-Hua Zhang
A series of fluorinated 7-hydroxycoumarin derivatives containing an oxime ether moiety have been designed, synthesized and evaluated for their antifungal activity. All the target compounds were determined by1H-NMR,13C-NMR, FTIR and HR-MS spectra. The single-crystal structures of compounds4e,4h,5hand6cwere further confirmed using X-ray diffraction. The antifungal activities againstBotrytis cinerea(B. cinerea),Alternariasolani(A. solani),Gibberella zeae(G. zeae),Rhizoctorzia solani(R. solani),Colletotrichum orbiculare(C. orbiculare) andAlternaria alternata(A. alternata) were evaluated in vitro. The preliminary bioassays showed that some of the designed compounds displayed the promising antifungal activities against the above tested fungi. Strikingly, the target compounds5fand6hexhibited outstanding antifungal activity againstB. cinereaat 100 μg/mL, with the corresponding inhibition rates reached 90.1 and 85.0%, which were better than the positive control Osthole (83.6%) and Azoxystrobin (46.5%). The compound5fwas identified as the promising fungicide candidate againstB. cinereawith the EC50values of 5.75 μg/mL, which was obviously better than Osthole (33.20 μg/mL) and Azoxystrobin (64.95 μg/mL). Meanwhile, the compound5fshowed remarkable antifungal activities againstR. solaniwith the EC50values of 28.96 μg/mL, which was better than Osthole (67.18 μg/mL) and equivalent to Azoxystrobin (21.34 μg/mL). The results provide a significant foundation for the search of novel fluorinated 7-hydroxycoumarin derivatives with good antifungal activity.Keywords:fluorinated 7-hydroxycoumarin;oxime ether derivatives;synthesis;crystal structure;antifungal activity
研究领域:
有机化学
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药物化学
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植物保护学
✓ 已验证
产品关联
DOI
PubMed
高影响因子
JOURNAL OF AGRICULTURAL AND FOOD CHEMISTRY
·
2024
·
IF 5.7
Bo Luo,Yuerui Wu,Xinran Ren,Huimin Li,Xuanru Li,Gege Wang,Mengjia Wang,Luqi Dong,Mengxing Liu,Wei Zhou,Lailiang Qu
In the search for novel succinate dehydrogenase inhibitor (SDHI) fungicides to control Rhizoctonia solani, thirty-five novel pyrazole-4-carboxamides bearing either an oxime ether or an oxime ester group were designed and prepared based on the strategy of molecular hybridization, and their antifungal activities against five plant pathogenic fungi were also investigated. The results indicated that the majority of the compounds containing oxime ether demonstrated outstanding in vitro antifungal activity against R. solani, and some compounds also displayed pronounced antifungal activities against Sclerotinia sclerotiorum and Botrytis cinerea. Particularly, compound 5e exhibited the most promising antifungal activity against R. solani with an EC50 value of 0.039 μg/mL, which was about 20-fold better than that of boscalid (EC50 = 0.799 μg/mL) and 4-fold more potent than fluxapyroxad (EC50 = 0.131 μg/mL). Moreover, the results of the detached leaf assay showed that compound 5e could suppress the growth of R. solani in rice leaves with significant protective efficacies (86.8%) at 100 μg/mL, superior to boscalid (68.1%) and fluxapyroxad (80.6%), indicating promising application prospects. In addition, the succinate dehydrogenase (SDH) enzymatic inhibition assay revealed that compound 5e generated remarkable SDH inhibition (IC50 = 2.04 μM), which was obviously more potent than those of boscalid (IC50 = 7.92 μM) and fluxapyroxad (IC50 = 6.15 μM). Furthermore, SEM analysis showed that compound 5e caused a remarkable disruption to the characteristic structure and morphology of R. solani hyphae, resulting in significant damage. The molecular docking analysis demonstrated that compound 5e could fit into the identical binding pocket of SDH through hydrogen bond interactions as well as fluxapyroxad, indicating that they had a similar antifungal mechanism. The density functional theory and electrostatic potential calculations provided useful information regarding electron distribution and electron transfer, which contributed to understanding the structural features and antifungal mechanism of the lead compound. These findings suggested that compound 5e could be a promising candidate for SDHI fungicides to control R. solani, warranting further investigation.
研究领域:
植物病理学
·
药物化学
✓ 已验证
DOI
PubMed
高影响因子
MOLECULAR DIVERSITY
·
2025
·
IF 3.8
Li Yong,Wu Taotao,Chen Guobin,He Jian,Zhang Yong,Zhang Qin,Zhou Pengfei,Chen Wenzhang,Fan Lingling
Twenty-eight novel phthalide derivatives incorporating thiazole, 1,3,4-oxadiazole, and oxime ether moieties were designed and synthesized using a pharmacophore hybridization strategy. Bioactivity assays demonstrated that compounds 1b , 1c , 4a , 4b and 4c exhibited moderate to excellent inhibitory activity against several specific fungi. Notably, compound 1b displayed superior antifungal efficacy against F. solani , F. oxysporum , B. dothidea , and V. mali compared to the commercial fungicides hymexazol and boscalid , with EC 50 values of 15.0 μ g/mL , 10.0 μ g/mL, 6.1 μ g/mL, and 11.4 μ g/mL, respectively. Additionally, compound 1b provided superior protective efficacy against B. dothidea- infected apples compared to boscalid. Preliminary mechanistic studies revealed that compound 1b could exert its antifungal activity by compromising the integrity of the hyphal cell membrane. This study highlights the potential of phthalide derivatives bearing dihalocarbonyl and oxime moieties as effective antifungal agents for controlling plant pathogenic fungi, warranting further investigation in the future. Graphical
研究领域:
药物化学
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抗菌剂
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真菌生物学
·
植物病理学
·
药效团杂交
✓ 已验证
DOI
PubMed
高影响因子
危险品化学品经营许可证（带存储）