TY - JOUR
T1 - Synthesis, crystal structures, and fungicidal activity of novel 1,5-diaryl-3-(glucopyranosyloxy)-1H-pyrazoles
AU - Liu, Yuan Yuan
AU - Shi, Hong
AU - He, Guang Ke
AU - Song, Guang Liang
AU - Zhu, Hong Jun
PY - 2012/9
Y1 - 2012/9
N2 - Five novel pyrazole-coupled glucosides, 1,5-diaryl-1H-pyrazol-3-yl 2,3,4,6-tetra-O-acetyl-β-D-glucopyranosides 5a-5e, were synthesized by the phase-transfer catalytic reaction of 1,5-diaryl-1H-pyrazol-3-ols 4a-4e with acetobromo-α-D-glucose in H 2O/CHCl 3 under alkaline conditions, using Bu 4N +Br - as catalyst. Then, glucosides 5a-5c were deacetylated in a solution of Na 2CO 3/MeOH to yield the 1,5-diaryl-3-(β-D-glucopyranosyloxy)-1H- pyrazoles 6a-6c. Their structures were characterized by 1H, 1H-COSY, 1H-, 13C-, and 19F-NMR spectroscopy, as well as elemental analysis. The structures of 5d and 6c were also determined by single-crystal X-ray diffraction analysis. A preliminary in vitro bioassay indicated that compounds 4e and 5d exhibited excellent-to-medium fungicidal activity against Sclerotinia sclerotiorum at the dosage of 10μg/ml.
AB - Five novel pyrazole-coupled glucosides, 1,5-diaryl-1H-pyrazol-3-yl 2,3,4,6-tetra-O-acetyl-β-D-glucopyranosides 5a-5e, were synthesized by the phase-transfer catalytic reaction of 1,5-diaryl-1H-pyrazol-3-ols 4a-4e with acetobromo-α-D-glucose in H 2O/CHCl 3 under alkaline conditions, using Bu 4N +Br - as catalyst. Then, glucosides 5a-5c were deacetylated in a solution of Na 2CO 3/MeOH to yield the 1,5-diaryl-3-(β-D-glucopyranosyloxy)-1H- pyrazoles 6a-6c. Their structures were characterized by 1H, 1H-COSY, 1H-, 13C-, and 19F-NMR spectroscopy, as well as elemental analysis. The structures of 5d and 6c were also determined by single-crystal X-ray diffraction analysis. A preliminary in vitro bioassay indicated that compounds 4e and 5d exhibited excellent-to-medium fungicidal activity against Sclerotinia sclerotiorum at the dosage of 10μg/ml.
KW - Fungicidal activity
KW - Glucosides
KW - Pyrazole-coupled glucosides
KW - Structure-activity relationship (SAR)
KW - X-Ray crystallography
UR - http://www.scopus.com/inward/record.url?scp=84866417877&partnerID=8YFLogxK
U2 - 10.1002/hlca.201100509
DO - 10.1002/hlca.201100509
M3 - 文章
AN - SCOPUS:84866417877
SN - 0018-019X
VL - 95
SP - 1645
EP - 1656
JO - Helvetica Chimica Acta
JF - Helvetica Chimica Acta
IS - 9
ER -