Citation: CHEN Hong, XU Wei, XU Fang, HE Xue-Lan, YUAN Mu. Synthesis, Crystal Structure and Cytotoxic Activity of a New NAN-190 Analogue[J]. Chinese Journal of Structural Chemistry, ;2014, 33(12): 1773-1778. doi: 10.14102/j.cnki.0254-5861.2011-0369 shu

Synthesis, Crystal Structure and Cytotoxic Activity of a New NAN-190 Analogue

1.
Pharmaceutical Research Center, Guangzhou Medical University, Guangzhou 510182, China

Received Date: 13 April 2014
Available Online: 18 July 2014
Fund Project: the China Postdoctoral Science Foundation (Nos. 2013M542165 and 2013M531837) (No. cx2d1127)

The NAN-190 analogue 2-(2-(2-(4-(2-methoxyphenyl)piperazin-1-yl)ethoxy)ethyl)isoindoline-1,3-dione (1, C₂₃H₂₇N₃O₄, M_r=409.48) was synthesized via a three-step reaction and characterized by ¹H NMR, ¹³C NMR, ESIMS and single-crystal X-ray diffraction. The crystal belongs to orthorhombic, space group Pna21 with a=7.6445(15), b=38.851(8), c=7.1316(14)Å, V=2118.0(7)Å³, Z=4, D_c=1.2840 mg/mm³, μ=0.089 mm^-1, F(000)=872.4, R=0.0545 and wR=0.1681. The single-crystal X-ray structural analysis reveals that the piperazine ring in compound 1 presents a stable and minimum energy chair conformation. In addition, the preliminary cytotoxic assay shows that the title compound exhibits strong and selective inhibitory activity against DU145 cells (IC₅₀=5.88±1.02 μM).
- NAN-190 analogue,
- synthesis,
- crystal structure,
- cytotoxic activity
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