Synthesis, Structure Characterization, and X-ray Crystallography of Novel 1-Benzyl-3-phenyl-1H-pyrazole-5-carboxylate Derivatives with a Carbohydrate Moiety

被引:0
作者
Lian, Song [1 ]
Liu, Jin-Ting [1 ]
Zheng, Liang-Wen [1 ]
Liu, Wei-Yong [1 ]
Zhao, Bao-Xiang [1 ]
机构
[1] Shandong Univ, Sch Chem & Chem Engn, Inst Organ Chem, Jinan 250100, Peoples R China
关键词
Synthesis; Structure; Pyrazole; Xylose; X-ray; LUNG-CANCER CELLS; PRELIMINARY BIOLOGICAL EVALUATION; POTENTIAL AGENTS; PYRAZIN-4(5H)-ONE DERIVATIVES; HYDRAZONE DERIVATIVES; COX-2; INHIBITORS; A549; DISCOVERY; APOPTOSIS; DESIGN;
D O I
10.1080/07328303.2011.583371
中图分类号
Q5 [生物化学]; Q7 [分子生物学];
学科分类号
071010 ; 081704 ;
摘要
A series of novel (2S,3R,4S,5R)-3,4,5-triacetoxy-tetrahydro-2H-pyran-2-yl 1-benzyl-3-phenyl-1H-pyrazole-5-carboxylate derivatives (3) were synthesized by the reaction of 2,3,4-tri-O-acetyl-alpha-D-xylopyranosyl bromide (2) and 1-benzyl-3-phenyl-1H-pyrazole-5-carboxylic acid (1) in the presence of sodium bicarbonate and tetrabutylammonium bromide in dichloromethane at reflux temperature. The structures of new compounds were determined by IR and (1)H NMR spectroscopy and HR mass spectrometry (HRMS), and the configuration of the newly generated chiral carbon (C-1) in the xylose ring was tentatively assigned based on the X-ray crystallographic structure of 3d and 3g.
引用
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页码:1 / 15
页数:15
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