Synthesis,Crystal Structure and Bioactivity of 1-(3-((Benzo[d][1,3]dioxol-5-yloxy)methyl)-phenethyl)-4-phenylpiperidin-4-ol  

作　　者：许星杰 徐未 陈洪 邵斌豪 

机构地区：[1]Pharmaceutical Research Center, Guangzhou Medical University

出　　处：《Chinese Journal of Structural Chemistry》2015年第12期1813-1818,共6页结构化学（英文）

基　　金：supported by the Natural Science Foundation of Guangdong Province(No.S2013040014088);the Postdoctoral Science Foundation of Guangzhou City(Q188)

摘　　要：The title compound 1-（3-（（benzo[d][1,3]dioxol-5-yloxy）methyl）phenethyl）-4- phenylpiperidin-4-ol （4, C27H29NO4, Mr = 431.51） was synthesized by a four-step reaction and characterized by 1H NMR, 13C NMR, elemental analysis and single-crystal X-ray diffraction. The crystal is of triclinic, space group P1 with a = 5.8033（12）, b = 10.705（2）, c = 18.393（4）A, a = 83A4（3）, β = 82.71（3）, γ = 88.88 （3）°, V= 1126.0（4） A3, Z= 1, Dc= 1.273 g/cm3, S = 1.070, p = 0.681 mm^-1, F（000） = 460, R = 0.0618 and wR = 0.1619 for 6452 observed reflections with I 〉 2σ（I） Geometry conformations revealed that the dihedral angle between benzodioxole and aromatic planes contributed to the formation of C-H…π interactions. Hydrogen bonds and van der waals interactions were observed to stabilize the three-dimensional packing structure. The compound showed a moderate inhibitory activity against the prostate cancer cells.The title compound 1-（3-（（benzo[d][1,3]dioxol-5-yloxy）methyl）phenethyl）-4- phenylpiperidin-4-ol （4, C27H29NO4, Mr = 431.51） was synthesized by a four-step reaction and characterized by 1H NMR, 13C NMR, elemental analysis and single-crystal X-ray diffraction. The crystal is of triclinic, space group P1 with a = 5.8033（12）, b = 10.705（2）, c = 18.393（4）A, a = 83A4（3）, β = 82.71（3）, γ = 88.88 （3）°, V= 1126.0（4） A3, Z= 1, Dc= 1.273 g/cm3, S = 1.070, p = 0.681 mm^-1, F（000） = 460, R = 0.0618 and wR = 0.1619 for 6452 observed reflections with I 〉 2σ（I） Geometry conformations revealed that the dihedral angle between benzodioxole and aromatic planes contributed to the formation of C-H…π interactions. Hydrogen bonds and van der waals interactions were observed to stabilize the three-dimensional packing structure. The compound showed a moderate inhibitory activity against the prostate cancer cells.

关 键 词：crystal structure phenylpiperidin prostate cancer C-H…π interactions SYNTHESIS 

分 类 号：O626[理学—有机化学] TQ460.1[理学—化学]