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Design, Syntheses and Biological Activities of Novel Sulfonylureas Containing an oxime ether Moiety

Chemical Research in Chinese Universities 2016年第2期32卷 195-201页

作者： WEI Wei CHENG Dandan CHEN Wei LIU Jingbo WAN Yingying LI Yuxin LI Yonghong YU Shujing LI Zhengming State Key Laboratory of Elemento-organic Chemistry Institute of Elemento-organic Chemistry Collaborative Innovation Center of Chemical Science and Engineering(Tianjin) Nankai University Tianjin 300071 P. R. China

Since sulfonylurea is one of the most potent acetohydroxyacid synthase（AHAS） inhibitors, a series of novel sulfonylureas containing an oxime ether moiety was designed and synthesized and their chemical structures were determined by means of 1H nuclear magnetic resonance（NMR）, 13C NMR and high-resolution mass spectrometry（HRMS）. In the herbicidal bioassay, several compounds showed moderate to good herbicidal activities against dicotyledons, but their activities against monocotyledons decreased. The in vitro antifungal activity was tested at a dosage of 50 mg/L. And the results show that compounds 71, 7m and 7n exhibit promising antifungal activities against six common plant pathogenic fungi. Further investigations on molecular modification are in progress.

关键词： Acetohydroxyacid synthase Sulfonylurea oxime ether

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Synthesis,Crystal Structure and Biological Activities of O-[(Z)-2-Methylbenzyl] 1-Phenyl-2-(1H-1,2,4-triazol-1-yl)ethanone oxime

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Chinese Journal of Structural Chemistry 2009年第3期28卷 307-310页

作者：蒙柳石德清 Key Laboratory of Pesticide and Chemical Biology of Ministry of Education College of Chemistry Central China Normal University

The crystal structure of the title compound （C18H18N4O, Mr = 306.36） has been determined by single-crystal X-ray diffraction. The crystal is of triclinic, space group P1 with α = 4.783（0）, b = 13.577（1）, c = 13.830（1） A, α = 63.581（2）, β = 88.326（2）, γ = 86.161（2）°, V= 802.5（1） A3, Z= 2, Dc = 1.268 g/cm^3, F（000） = 324, μ（MoKa） = 0.082 mm^-1, the final R = 0.0497 and wR = 0.1199 for 3094 observed reflections （I 〉 2σ（I））. The dihedral angles between the phenyl （C（1）-C（4）-（6）） and triazole, the phenyl （C（13）-C（15）-C（18）） and triazole, and the two phenyl rings are 7.9（1）, 69.9（1） and 67.8（1）°, respectively. Strong C-H…π interaction joins molecules into a chain along the c axis and contributes to the stability of the structure. Preliminary bioassay results show that the title compound possesses excellent and selective fungicidal activity against Colletotrichum gossypii but displays moderate to weak insecticidal activity against aphides.

关键词： crystal structure synthesis oxime ether biological activity

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Synthesis and Crystal Structure of (E)-2-phenyl-6,7dihydrobenzofuran-4(5H)-one O-cyanomethyl oxime

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Chinese Journal of Structural Chemistry 2013年第9期32卷 1334-1338页

作者：金蕾方胡彪曹成桥黄年玉邹坤汪鋆植 Hubei Key Laboratory of Natural Products Research and Development College of Chemistry and Life Sciences China Three Gorges University Hubei Tujia Institute of Medicine

A pair of E/Z-isomers of 2-phenyl-6,7-dihydrobenzofuran-4（5H）-one O-cyanomethyl oxime,C16H14N2O2,as potential drugs for treating peptic ulcer and other acid-related diseases have been synthesized and characterized by IR,MS and NMR spectra.Meanwhile,the crystal of IIIa was obtained and determined by X-ray single-crystal diffraction.Crystal data： monoclinic system,space group P21 /c,a = 8.423（8）,b = 19.596（16）,c = 8.770（8）,β = 107.750（12）°,V = 1379（2）3,Z = 4,F（000） = 560,Dc = 1.283 g/cm3,μ = 0.086 mm 1,R = 0.0681 and wR = 0.2029 for 14472 independent reflections（Rint = 0.0782） and 2428 observed ones（I 2σ（I））.

关键词： X-ray diffraction crystal structure oxime ether H＋/K＋-ATPase inhibitory activity cytotoxic activity

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