Citation: CHEN Chao-Yue, HE Qin-Ting, SUN Da-Dong, HU Jin-Song. Crystal Structure and Antiproliferative Activity of Ethyl 3,9-Dihydroxy-9-methyl-7-phenyl-7,8,10-trihydro-6H-dibenzo[b,d]pyran-6-one-8-carboxylate[J]. Chinese Journal of Structural Chemistry, ;2016, 35(2): 199-204. doi: 10.14102/j.cnki.0254-5861.2011-0931 shu

Crystal Structure and Antiproliferative Activity of Ethyl 3,9-Dihydroxy-9-methyl-7-phenyl-7,8,10-trihydro-6H-dibenzo[b,d]pyran-6-one-8-carboxylate

1.
a School of Chemistry and Environmental Engineering, Jiangsu University of Technology, Changzhou, Jiangsu 213001, China;
2.
b School of Chemical Engineering, Anhui University of Science and Technology, Huainan, Anhui 232001, China

Received Date: 6 August 2015
Available Online: 9 November 2015
Fund Project:

Ethyl 3,9-dihydroxy-9-methyl-7-phenyl-7,8,10-trihydro-6H-dibenzo[b,d]pyran-6-one-8-carboxylate (C₂₃H₂₂O₆, M_r = 394.42) has been synthesized and its structure was determined by ¹H and ¹³C NMR, ESI-MS, elemental analysis, and X-ray single-crystal diffraction. The crystal belongs to the triclinic system, space group P1, with a = 8.8220(17), b = 9.881(2), c = 12.157(2) Å, α = 90.488(3), β = 102.664(4), γ = 98.799(3)°, V = 1020.8(3) Å³, Z = 2, D_c = 1.342 g/cm³, μ = 0.099 mm^-1, F(000) = 436, R = 0.0615 and wR = 0.2501 for 2592 observed reflections with (I > 2σ(I)). In the crystal structure, the coumarin ring system is planar and the 3:4 fused cyclohexane ring adopts distorted half-chair conformation. Rich hydrogen bonding interactions are formed between compound 2 and lattice water molecules. These interactions assemble molecules of 2 into 2D layered networks in an AB stacking sequence. Its in vitro antiproliferative activities against three human cancer cell lines were evaluated by MTT assay.
- coumarin,
- 6H-dibenzo[b,d]pyran-6-one,
- crystal structure,
- antiproliferative activity
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沈阳化工大学材料科学与工程学院沈阳 110142