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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
| Content Provider | MDPI |
|---|---|
| Author | Ahn, Seunghyun Sung, Jiha Lee, Ji Hye Yoo, Miri Lim, Yoongho Shin, Soon Young Koh, Dongsoo |
| Copyright Year | 2020 |
| Description | 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. |
| Starting Page | 413 |
| e-ISSN | 20734352 |
| DOI | 10.3390/cryst10050413 |
| Journal | Crystals |
| Issue Number | 5 |
| Volume Number | 10 |
| Language | English |
| Publisher | MDPI |
| Publisher Date | 2020-05-20 |
| Access Restriction | Open |
| Subject Keyword | Crystals Organic Chemistry Atomic, Molecular and Chemical Physics Isoflavone Crystal Structure Hydrogen Bonding in Silico Docking Hirshfeld Surface Dft |
| Content Type | Text |
| Resource Type | Article |
