Citation: GU Wen MIAO, WANG Shi-Fa, HAO Yun, ZHANG Kang-Ping, JIN Xiao-Yan. Synthesis, Crystal Structure and Antitumor Activity of a New 3H-Phenanthro- [2,1-d]imidazole Derivative of Dehydroabietic Acid[J]. Chinese Journal of Structural Chemistry, ;2015, 34(9): 1440-1445. doi: 10.14102/j.cnki.0254-5861.2011-0766 shu

Synthesis, Crystal Structure and Antitumor Activity of a New 3H-Phenanthro- [2,1-d]imidazole Derivative of Dehydroabietic Acid

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

Received Date: 4 April 2015
Available Online: 15 July 2015
Fund Project: Project supported by the National Natural Science Foundation of China (31000273) (31000273)

The title compound (C₁₉H₂₄BrN₃O₂, 3) was synthesized from dehydroabietic acid and its crystal structure was determined by single-crystal X-ray diffraction. The compound is of monoclinic system, space group C2 with a=24.830(5), b=7.1410(14), c=13.981(3) Å, β=107.68(3)°, Z=4, V=2361.9(8) Å³, M_r=482.42, D_c=1.357 Mg/m³, S=1.003 , μ=1.772 mm^-1, F(000)=1008, the final R=0.0660 and wR=0.1402 for 2244 observed reflections (I>2σ(I)). The crystal structure is stabilized by four hydrogen bonds (O(W)-H(WA)···O(3), O(W)-H(WB)···O(1), N(2)-H(2A)···O(W) and N(3)-H(3A)···N(1)) formed among the title compound, the crystal water and acetone molecules. The preliminary antitumor assay showed the title compound exhibited considerable inhibitory activity against HepG2 and SMMC-7721 cell lines with the IC₅₀ values of 17.1 and 10.2 μM, respectively.
- dehydroabietic acid,
- 3H-phenanthro[2,1-d]imidazole,
- crystal structure,
- antitumor activity
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