Abstract
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.
Highlights
Flavonoids are widely distributed in plants, performing interactions as secondary metabolites.One of the characteristic flavonoid features is phytoalexins, which show self-defense abilities in plants.The self-defense system of flavonoids has been extensively modified to apply it to medicinal chemistry and has demonstrated antioxidant, anti-proliferative, anti-tumor, anti-microbial, anti-inflammatory and anti-cardiovascular disease properties [1,2,3,4,5,6,7,8]
The isoflavone compound 6 was prepared according to literature methods as shown in Scheme 1 [24,25]
The resulting solid was filtered and washed with cold methanol to give intermediate enamine (3) which was used for the reaction without further purification
Summary
Flavonoids are widely distributed in plants, performing interactions as secondary metabolites.One of the characteristic flavonoid features is phytoalexins, which show self-defense abilities in plants.The self-defense system of flavonoids has been extensively modified to apply it to medicinal chemistry and has demonstrated antioxidant, anti-proliferative, anti-tumor, anti-microbial, anti-inflammatory and anti-cardiovascular disease properties [1,2,3,4,5,6,7,8]. One of the characteristic flavonoid features is phytoalexins, which show self-defense abilities in plants. A recent review describes that flavones are one of the most important scaffolds for medicinal chemistry and their applications in pharmaceutical research are extremely diverse [10]. In silico methods, such as molecular docking, have been widely used in the target research of bioactive compounds, and the complete three-dimensional structures of substrates and proteins are the prerequisites for these processes [11,12,13]
Sign-in/Register to view highlights & summary Sign-in/Register to access full text options 
Free) 
Talk to us
Join us for a 30 min session where you can share your feedback and ask us any queries you have
Schedule a call
