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

作者：Hong Yan-Ping^*; Shangguan Xin-Chen; Li Dong-Ming

来源：Chinese Journal of Structural Chemistry, 2013, 32(11): 1639-1646.

DOI：10.14102/j.cnki.0254-5861.2013.11.006

• alpha-aminophosphonate
• pyrazole
• crystal structure
• bioactivities
• synthesis

Using 3-amino-4-cyanopyrazole, salicylaldehyde and dialkylphosphite as materials, a series of alpha-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, H-1 NMR, C-13 NMR and elemental analysis. The crystal structure of diisobutyl{alpha[3(4-cyano-1H-pyrazol)amino)]-N-(2-hydroxylbenzy1)}phosphonate (4d, C19H27N4O4P) was determined 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) angstrom, V = 4328.7(17) angstrom 3, M-r = 406.42, D-c = 1.247 g/cm(3), Z = 8, F(000) = 1728, mu = 0.158 mm(-1), MoKa radiation (lambda = 0.71073 angstrom), the final R = 0.064 and wR = 0.0169 for observed reflections with I> 2 sigma(I). X-ray diffraction analysis reveals that two planes lie in 4d, and the dihedral angle is 85.76 degrees. Intermolecular O(1)-H(1B)center dot center dot center dot O(2), N(1)-H(1)center dot center dot center dot N(4), N(3)-H(3)center dot center dot center dot N(2) and N(3)-H(3)center dot center dot center dot 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 mu g/mL, and 4e possessed excellent antitumor activity against PC3 cells at 10 mu mol/L.

• 出版日期2013
• 单位江西农业大学