Efficient synthesis, structure elucidation, and anti-parasitic activities of novel quinolinyl β–enaminones

Synthesis of 1‐phenyl‐3‐(quinolin‐8‐ylamino)prop‐2‐en‐1‐one and analysis of its structure by X‐ray crystallography, NMR, UV‐Vis spectroscopy and DFT calculations

“…The strong difference in the NMR spectra of these solutions can be explained by the different polarity of the solvent molecules, [42][43][44][45][46] since the electric dipole moments of the solvent molecules affect the distribution of electron density throughout the molecule of the studied substance and, consequently, on the degree of shielding of nuclei by their electron shells. This substance has already been studied by NMR in deuterated chloroform [6] (it should be noted that the authors of that paper made a misprint when interpreting the 1 H NMR spectrum of this compound -the proton with δ = 13.34 ppm was designated by them as H 3a , but it would be correct to denote that as H 8b ). Despite the fact that the 1 H NMR spectra of the substance in chloroform and carbon tetrachloride differ from each other, many of the splitting constants of the 1 H NMR signals are almost the same (for example, 12.9 Hz vs. 12.7 Hz for the proton H11, 8.0 Hz vs. 8.1 Hz for the proton H13, 4.2 Hz vs. 4.0 Hz for the proton H10, 8.0 Hz vs. 8.1 Hz for the proton H8, 8.0 Hz vs. 7.9 Hz for the protons H16 and H20).…”

“…These compounds are widely used in the creation of antibacterial, antidiabetic, anti-inflammatory, anticonvulsant and antitumor agents. [5,6] β-enaminone molecules having a chelate structure are wide used as ligand systems. [7][8][9][10][11] The presence of double bonds in β-enaminone molecules determines the possibility of their cis-trans isomerization.…”

“…[7][8][9][10][11] The presence of double bonds in β-enaminone molecules determines the possibility of their cis-trans isomerization. The study of isomerization processes of β-enaminones is important for both applied and fundamental science [12,6] and NMR, UV spectroscopy and some other methods are suitable for this. [13][14][15] In this work the synthesis, structure and identification of isomers of 1-phenyl-3-(quinolin-8-ylamino)prop-2-en-1-one is considered.…”

“…β‐enaminones are of particular interest as biologically active substances. These compounds are widely used in the creation of antibacterial, antidiabetic, anti‐inflammatory, anticonvulsant and antitumor agents [5,6] . β‐enaminone molecules having a chelate structure are wide used as ligand systems [7–11] .…”

“…The presence of double bonds in β‐enaminone molecules determines the possibility of their cis‐trans isomerization. The study of isomerization processes of β‐enaminones is important for both applied and fundamental science [12,6] and NMR, UV spectroscopy and some other methods are suitable for this [13–15] …”