Citation:
XU Xing-Jie, XU Wei, CHEN Hong, SHAO Bin-Hao. Synthesis, Crystal Structure and Bioactivity of 1-(3-((Benzo[d][1,3]dioxol-5-yloxy)methyl)-phenethyl)-4-phenylpiperidin-4-ol[J]. Chinese Journal of Structural Chemistry,
2015, 34(12): 1813-1818.
doi:
10.14102/j.cnki.0254-5861.2011-0787
Synthesis, Crystal Structure and Bioactivity of 1-(3-((Benzo[d][1,3]dioxol-5-yloxy)methyl)-phenethyl)-4-phenylpiperidin-4-ol
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) Å, α=83.44(3), β=82.71(3), γ=88.88 (3)°, V=1126.0(4) Å3, Z=1, Dc=1.273 g/cm3, S=1.070, μ=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.
English
Synthesis, Crystal Structure and Bioactivity of 1-(3-((Benzo[d][1,3]dioxol-5-yloxy)methyl)-phenethyl)-4-phenylpiperidin-4-ol
Abstract:
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) Å, α=83.44(3), β=82.71(3), γ=88.88 (3)°, V=1126.0(4) Å3, Z=1, Dc=1.273 g/cm3, S=1.070, μ=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.
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Key words:
- crystal structure
- / phenylpiperidin
- / prostate cancer
- / C-H…π interactions
- / synthesis
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