- Novel fluorinated 7-hydroxycoumarin derivatives containing an oxime ether moiety: Design, synthesis, crystal structure and biological evaluation
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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 compounds 4e, 4h, 5h and 6c were further confirmed using X-ray diffraction. The antifungal activities against Botrytis cinerea (B. cinerea), Alternaria solani (A. solani), Gibberella zeae (G. zeae), Rhizoctorzia solani (R. solani), Colletotrichum orbiculare (C. orbiculare) and Alternaria 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 compounds 5f and 6h exhibited outstanding antifungal activity against B. cinerea at 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 compound 5f was identified as the promising fungicide candidate against B. cinerea with the EC50 values of 5.75 μg/mL, which was obviously better than Osthole (33.20 μg/mL) and Azoxystrobin (64.95 μg/mL). Meanwhile, the compound 5f showed remarkable antifungal activities against R. solani with the EC50 values 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.
- Dai, Peng,Jiao, Jian,Wang, Qing-Qing,Zhang, Shu-Guang,Zhang, Wei-Hua
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- Synthesis of osthol-based botanical fungicides and their antifungal application in crop protection
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Plant pathogenic fungi decrease the quality and productivity of plant production. The botanical fungicides have better biocompatibility and rapid biodegradation, little or no cross resistance, and the structural diversity, and thus are beneficial to deal with plant fungal diseases. Osthole has been widely used as the commercial botanical fungicide against powdery mildew in China. In this article, a series of osthole derivatives were synthesized, which respectively contain different substituents on the benzene ring, at the C8-position and pyrone ring. All the target compounds were evaluated in vitro for their antifungal activity against resistant phytopathogenic fungi. Colletotrichum fragariae, Strawberry Botrytis Cinerea, Kiwifruit Botrytis Cinerea, Kiwifruit brown Rots, which are common in fruit fungal diseases. The compound C4 was identified as the most promising candidate with the EC50 values at 38.7 μg/mL against Colletotrichum Fragariae, 14.5 μg/mL against Strawberry Botrytis Cinerea and 24.3 μg/mL against Kiwifruit Botrytis Cinerea, respectively, whereas the antifungal activity against resistant phytopathogenic fungi. of osthole is too low to be used (EC50 > 400 ppm). The results of mycelial relative conductivity determination, PI uptake and fluorescence spectroscopy indicated that the cell membrane of fungi is the key action site of C4. Besides, C4 has the potent inhibitory activity against both of plant and human pathogenic bacteria. Our studies showed that C4 was worthy for further attention as a promising botanical fungicide candidate in crop protection.
- Guo, Yuying,Chen, Jiabao,Ren, Dan,Du, Bo,Wu, Lei,Zhang, Yuanyuan,Wang, Zhouyu,Qian, Shan
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- 4-trifluoromethyl-7-hydroxycoumarin derivative as well as preparation method and application thereof
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The invention discloses a 4-trifluoromethyl-7-hydroxycoumarin derivative as well as a preparation method and application thereof. The yield of the preparation method is high. The invention also discloses application of the 4-trifluoromethyl-7-hydroxycoumarin derivative to an agricultural anti-fungal aspect. An inventor detects the toxicity effect on rice sheath blight disease, colletotrichum lagenarium, fusarium graminearum, strawberry botrytis cinerea, apple spot germs and alternaria solani by a growth rate method; certain lateral reactivity is realized on the 4-trifluoromethyl-7-hydroxycoumarin derivative; the activity of individual compounds is superior to that of contrast medicine; the effect of the compound in the aspect of inhibiting the rice sheath blight disease is prominent; or the compound can become a lead compound molecule for developing and creating new pesticide.
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Paragraph 0056-0060; 0064; 0069-0071
(2018/03/01)
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- Microwave-assisted Synthesis and antifungal activity of coumarin[8,7-e][1,3]oxazine derivatives
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The synthesis of novel coumarin[8,7-e][1,3]oxazine derivatives through a microwave-assisted three-component one-pot Mannich reaction is described in this study. All the target compounds were evaluated in vitro for their antifungal activity against Botryti
- Zhang, Ming-Zhi,Zhang, Rong-Rong,Yin, Wen-Zheng,Yu, Xiang,Zhang, Ya-Ling,Liu, Pin,Gu, Yu-Cheng,Zhang, Wei-Hua
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p. 611 - 618
(2016/07/12)
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- Rational design, synthesis, evaluation and enzyme - Substrate structures of improved fluorogenic substrates for family 6 glycoside hydrolases
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Methylumbelliferyl-β-cellobioside (MUF-G2) is a convenient fluorogenic substrate for certain β-glycoside hydrolases (GH). However, hydrolysis of the aglycone is poor with GH family 6 enzymes (GH6), despite strong binding. Prediction of the orientation of the aglycone of MUF-G2 in the +1 subsite of Hypocrea jecorina Cel6A by automated docking suggested umbelliferyl modifications at C4 and C6 for improved recognition. Four modified umbelliferyl-β-cellobiosides [6-chloro-4-methyl- (ClMUF); 6-chloro-4-trifluoromethyl- (ClF3MUF); 4-phenyl- (PhUF); 6-chloro-4-phenyl- (ClPhUF)] were synthesized and tested with GH6, GH7, GH9, GH5 and GH45 cellulases. Indeed the rate of aglycone release by H. jecorina Cel6A was 10-150 times higher than with MUF-G2, although it was still three orders of magnitude lower than with H. jecorina Cel7B. The 4-phenyl substitution drastically reduced the fluorescence intensity of the free aglycone, while ClMUF-G2 could be used for determination of kcat and KM for H. jecorina Cel6A and Thermobifida fusca Cel6A. Crystal structures of H. jecorina Cel6A D221A mutant soaked with the MUF-, ClMUF- and ClPhUF-β-cellobioside substrates show that the modifications turned the umbelliferyl group 'upside down', with the glycosidic bond better positioned for protonation than with MUF-G2. 2012 The Authors Journal compilation
- Wu, Miao,Nerinckx, Wim,Piens, Kathleen,Ishida, Takuya,Hansson, Henrik,Sandgren, Mats,Stahlberg, Jerry
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p. 184 - 198
(2013/03/28)
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- Design and synthesis of potent and subtype-selective PPARα agonists
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Beginning with a moderately potent PPARγ agonist 9, a series of potent and highly subtype-selective PPARα agonists was identified through a systematic SAR study. Based on the results of the efficacy studies in the hamster and dog models of dyslipidemia and the desired pharmacokinetic data, the optimized compound 39 was selected for further profiling.
- Desai, Ranjit C.,Metzger, Edward,Santini, Conrad,Meinke, Peter T.,Heck, James V.,Berger, Joel P.,MacNaul, Karen L.,Cai, Tian-Quan,Wright, Samuel D.,Agrawal, Arun,Moller, David E.,Sahoo, Soumya P.
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p. 1673 - 1678
(2007/10/03)
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