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Synthesis, Single Crystal X-Ray Structure, Hirshfeld Surface Analysis, DFT Computations, Docking Studies on Aurora Kinases and an Anticancer Property of 3-(2,3-Dihydrobenzo[b][1,4]dioxin-6-yl)-6-methoxy-4H-chromen-4-one

1
Department of Applied Chemistry, Dongduk Women’s University, Seoul 02748, Korea
2
Division of Bioscience and Biotechnology, BBRC, Konkuk University, Seoul 05029, Korea
3
Department of Biological Chemistry, Konkuk University, Seoul 05029, Korea
*
Authors to whom correspondence should be addressed.
S.A. and J.S. contributed equally to this work.
Crystals 2020, 10(5), 413; https://doi.org/10.3390/cryst10050413
Received: 20 April 2020 / Revised: 9 May 2020 / Accepted: 19 May 2020 / Published: 20 May 2020
The isoflavone compound 3-(2,3-dihydrobenzo[b][1,4]dioxin-6-yl)-6-methoxy-4H-chromen-4-one (6) was prepared and structurally characterized using NMR, mass spectrum and X-ray crystallography. Compound 6, C18H14O5, was crystallized in the monoclinic space group P21/n with the cell parameters; a = 7.1869(4) Å, b = 10.2764(6) Å, c = 19.6771(10) Å, β = 99.442(2)°, V = 1433.57(14) Å3, Z = 4. In the title compound, the chromenone ring system is slightly twisted from planarity and the dihedral angle formed between the plane of the chromenone ring and benzene ring is 47.75°. Several intermolecular hydrogen bonds make the crystal stabilized in the three-dimensional structure, which was confirmed by Hirshfeld surface analysis. Density functional theory (DFT) calculations at the B3LYP/6-311++G(d,p) level were carried out and the calculated geometric parameters were compared with the experimental results. A frontier molecular orbital calculation was performed to reveal that the energy values of highest occupied molecular orbital (HOMO) and lowest un-occupied molecular orbital (LUMO) were −5.8223 eV and −1.8447 eV, and the HOMO–LUMO energy gap was 3.9783 eV. A clonogenic long-term survival assay of compound 6 against HCT116 human colon cancer cells showed an anti-cancer ability, with GI50 value of 24.9 μM. Docking experiments within the active sites of aurora kinase A and B were carried out to explain the anti-cancer property of compound 6. View Full-Text
Keywords: isoflavone; crystal structure; hydrogen bonding; in silico docking; Hirshfeld surface; DFT isoflavone; crystal structure; hydrogen bonding; in silico docking; Hirshfeld surface; DFT
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Ahn, S.; Sung, J.; Lee, J.H.; Yoo, M.; Lim, Y.; Shin, S.Y.; Koh, D. Synthesis, Single Crystal X-Ray Structure, Hirshfeld Surface Analysis, DFT Computations, Docking Studies on Aurora Kinases and an Anticancer Property of 3-(2,3-Dihydrobenzo[b][1,4]dioxin-6-yl)-6-methoxy-4H-chromen-4-one. Crystals 2020, 10, 413.

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