Citation: HAO Yun, HUA Da-Wei, MIAO Ting-Ting, WANG Shi-Fa, JIN Xiao-Yan, GU Wen. Synthesis, Crystal Structure and Antitumor Activity of a New Indolequinone Derivative of Ursolic Acid[J]. Chinese Journal of Structural Chemistry, ;2016, 35(8): 1167-1173. doi: 10.14102/j.cnki.0254-5861.2011-1092 shu

Synthesis, Crystal Structure and Antitumor Activity of a New Indolequinone Derivative of Ursolic Acid

1.
Jiangsu Key Lab of Biomass-based Green Fuels and Chemicals, College of Chemical Engineering, Nanjing Forestry University, Nanjing 210037, China

Received Date: 21 December 2015
Available Online: 10 May 2016
Fund Project: Project supported by the Natural Science Foundation of Jiangsu Province (BK20151516) (BK20151516)

The title compound (C₃₇H₄₈BrNO₅, 6) was synthesized from ursolic acid and its crystal structure was determined by single-crystal X-ray diffraction analysis. The compound is of orthorhombic system, space group P2₁2₁2₁ with a=16.846(3), b=18.844(4), c=11.262(2)Å, Z=4, V=3575.1(13)Å³, M_r=666.67, D_c=1.239 Mg/m³, S=1.002, μ=1.190 mm^-1, F(000)=1408, the final R=0.0831 and wR=0.1459 for 2286 observed reflections (I>2σ(I)). The crystal structure is stabilized by two intermolecular hydrogen bonds (N-H(0A)…O(2) and O(1)-H(1A)…O(3)). In the preliminary antitumor assay, the title compound 6 exhibits potent cytotoxic activity against HepG2 and SMMC-7721 cells with IC₅₀ values of 1.64±0.21 and 1.22±0.13 μM, respectively.
- ursolic acid,
- indolequinone,
- crystal structure,
- antitumor activity
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