Synthesis and detailed characterization of a newly synthesized chalcone, 3-(2,5-dimethoxyphenyl)-1-(naphthalen-2-yl)prop-2-en-1-one

Abstract

Chalcones are the main component of some natural compounds. The title compound, 3-(2,5-dimethoxyphenyl)-1-(naphthalen-2-yl)prop-2-en-1-one, was synthesized and characterized. The compound (C21H18O3) crystallizes in the triclinic system with the space group of P-1 (no. 2), a = 7.7705(4) Å, b = 10.2634(6) Å, c = 11.2487(6) Å, α = 79.655(5)°, β = 81.500(5)°, γ = 68.039(5)°, V = 815.28(9) Å3, Z = 2, T = 293(2) K, μ(MoKα) = 0.086 mm-1, Dcalc = 1.297 g/cm3, 9126 reflections measured (4.318° ≤ 2Θ ≤ 52.728°), 3302 unique (Rint = 0.0466, Rsigma = 0.0528) which were used in all calculations. The final R1 was 0.0568 (I > 2σ(I)) and wR2 was 0.1667 (all data). The crystal structure is stabilized by both short C-H···O inter- and intra-molecular interactions. In addition, the crystal structure is reinforced by π-π interactions. Hirshfeld surface analysis confirmed the presence of C-H···O intermolecular interactions. The two-dimensional fingerprint plots are used to visualize the individual interactions present in the molecule. DFT calculations were performed to know the energy levels of the frontier molecular orbitals (HOMO-LUMO). The energy gap between the frontier molecular orbitals shows the kinetic stability of the molecule. The chemical reactive sites are observed by generating MEP surface. Non-covalent interactions (NCIs) are analyzed using reduced density gradient (RDG) analysis.

Structural and theoretical exploration of a multi-methoxy chalcone: Synthesis, quantum theory, electrostatics, molecular packing, DFT analysis, and in-silico anti-cancer evaluation

“…Covalent regions between carbon-carbon atoms are predominantly red. Additionally, the blue circles around carbon atoms denote electron depletion regions between inner shell and valence shell [ 52 ].

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Synthesis, reactions, and applications of chalcones: A review

“…Chalcone may be called some names as benzylideneacetophenone, phenyl styryl ketone, benzalacetophenone, α-phenyl-β-benzoylethylene, and others [3,4]. Many of chalcones possess interesting pharmacological properties such as antibacterial [5], antifungal [6], antiviral [7], anti-HIV activity [8], 5-lipoxygenase inhibitor [9], anticancer [10][11][12], cytotoxic activity [13], antimalarial [14], antiulcer [15], antileishmanial [16], and anti-inflammatory [17]. Recently, several chalcone-based compounds have been approved for clinical use, for example Metochalcone I was once marketed as a choleretic drug, while Sofalcone II was previously used as an antiulcer and nucoprotective drug (Figure 2) [18].…”