119179-66-7Relevant articles and documents
Novel fluorinated 7-hydroxycoumarin derivatives containing an oxime ether moiety: Design, synthesis, crystal structure and biological evaluation
Dai, Peng,Jiao, Jian,Wang, Qing-Qing,Zhang, Shu-Guang,Zhang, Wei-Hua
, (2021)
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.
4-trifluoromethyl-7-hydroxycoumarin derivative as well as preparation method and application thereof
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Paragraph 0056-0060; 0064; 0069-0071, (2018/03/01)
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.
Rational design, synthesis, evaluation and enzyme - Substrate structures of improved fluorogenic substrates for family 6 glycoside hydrolases
Wu, Miao,Nerinckx, Wim,Piens, Kathleen,Ishida, Takuya,Hansson, Henrik,Sandgren, Mats,Stahlberg, Jerry
, p. 184 - 198 (2013/03/28)
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