Microwave-assisted Syntheses,Structures and Bioactivities of α-Aminophosphonates Containing Pyrazole and 2-Hydroxybenzyl Units  

作　　者：洪艳平 上官新晨 黎冬明 

机构地区：[1]Jiangxi Key Laboratory of Natural Product and Functional Food,College of Food Science and Engineering,Jiangxi Agricultural University

出　　处：《Chinese Journal of Structural Chemistry》2013年第11期1639-1646,共8页结构化学（英文）

基　　金：Future Talent Project of JiangxiAgricultural University(No.09003444)

摘　　要：Using 3-amino-4-cyanopyrazole, salicylaldehyde and dialkylphosphite as materials, a series of a-aminophosphonates containing pyrazole and 2-hydroxybenzyl units were synthesized under microwave irradiation without solvents and catalysts. The structures of the compounds were verified by IR, 1H NMR, J3C NMR and elemental analysis. The crystal structure of diisobutyl {a-[3- （4-cyano-lH-pyrazol）amino）]-N-（2-hydroxylbenzyl）}phosphonate （4d, C19H27N404P） was deter- mined by single-crystal X-ray diffraction. Compound 4d crystallizes in the orthorhombic system, space group Pbcn with a = 17.329（4）, b = 20.091（5）, c = 12.433（3）/k, V = 4328.7（17） A3, M,. = 406.42, Dc = 1.247 g/cm3, Z = 8, F（000） = 1728,μ = 0.158 mm-1, MoKa radiation （2 = 0.71073 A）, the final R = 0.064 and wR = 0.0169 for observed reflections with I 〉 2σ（I）. X-ray diffraction analysis reveals that two planes lie in 4d, and the dihedral angle is 85.76°. Intermolecular O（1）-H（1B）-O（2）, N（1）-H（1）-N（4）, N（3）-H（3）.-.N（2） and N（3）-H（3）...O（1） hydrogen bonds are found in the structure. All the compounds were evaluated for their antiviral and antitumor activities respectively. Among them, 4d and 4e showed moderate anti-TMV activities at 500 gg/mL, and 4e possessed excellent antitumor activity against PC3 cells at 10 gmol/L.Using 3-amino-4-cyanopyrazole, salicylaldehyde and dialkylphosphite as materials, a series of a-aminophosphonates containing pyrazole and 2-hydroxybenzyl units were synthesized under microwave irradiation without solvents and catalysts. The structures of the compounds were verified by IR, 1H NMR, J3C NMR and elemental analysis. The crystal structure of diisobutyl {a-[3- （4-cyano-lH-pyrazol）amino）]-N-（2-hydroxylbenzyl）}phosphonate （4d, C19H27N404P） was deter- mined by single-crystal X-ray diffraction. Compound 4d crystallizes in the orthorhombic system, space group Pbcn with a = 17.329（4）, b = 20.091（5）, c = 12.433（3）/k, V = 4328.7（17） A3, M,. = 406.42, Dc = 1.247 g/cm3, Z = 8, F（000） = 1728,μ = 0.158 mm-1, MoKa radiation （2 = 0.71073 A）, the final R = 0.064 and wR = 0.0169 for observed reflections with I 〉 2σ（I）. X-ray diffraction analysis reveals that two planes lie in 4d, and the dihedral angle is 85.76°. Intermolecular O（1）-H（1B）-O（2）, N（1）-H（1）-N（4）, N（3）-H（3）.-.N（2） and N（3）-H（3）...O（1） hydrogen bonds are found in the structure. All the compounds were evaluated for their antiviral and antitumor activities respectively. Among them, 4d and 4e showed moderate anti-TMV activities at 500 gg/mL, and 4e possessed excellent antitumor activity against PC3 cells at 10 gmol/L.

关 键 词：a-aminophosphonate PYRAZOLE crystal structure BIOACTIVITIES synthesis 

分 类 号：O626.3[理学—有机化学]