731001-97-1Relevant academic research and scientific papers
Synthesis of tetranuclear complex of Pd(II) with thiosemicarbazone ligands derived from 2-quinolone and its catalytic evaluation in Suzuki–Miyaura-type coupling reactions and alkoxylation of chloroquinolines
Nandhini, Sundar,Dharani, Sivadasan,Elamathi, Chennakrishnan,Dallemer, Frederic,Prabhakaran, Rathinasabapathi
, (2021/09/06)
A tetranuclear palladium(II) complex [(Pd(H-6MOQtsc-Ph))4] was obtained from the reaction between 6-methyl-2-oxo-1,2-dihydroquinoline-3-carboxaldehyde-4(N)-phenylthiosemicarbazone [H2-6MOQtsc-Ph] and K2[PdCl4]. The ligand and the Pd(II) complex were characterized by Fourier transform infrared spectroscopy (FT-IR), UV–visible and 1H NMR spectroscopy. X-ray diffraction studies confirmed the tetrameric nature of the complex with the coordination of ligand through quinolone carbonyl, azomethine nitrogen and thiolate sulfur atoms, and the fourth site is occupied by 2-quinolone nitrogen atom of the adjacent ligand. The synthesized complex was tested as catalyst in Suzuki–Miyaura coupling reaction between various chloroquinoline derivatives with phenylboronic acid. The reactions afforded unexpected C-alkoxylated (C-O coupling) products instead of more expected C-arylated (C-C coupling) products in the respective alcoholic mediums. However, the reactions with traditional aryl halides probed with very good yield of the corresponding C-C coupling products.
Synthesis and Antibacterial, Antioxidant, and Molecular Docking Analysis of Some Novel Quinoline Derivatives
Belay, Zerihun,Eswaramoorthy, Rajalakshmanan,Melaku, Yadessa,Zeleke, Digafie
, (2020/08/17)
2-Chloroquinoline-3-carbaldehyde and 2-chloro-8-methylquinoline-3-carbaldehyde derivatives were synthesized through Vilsmeier formulation of acetanilide and N-(o-tolyl)acetamide. Aromatic nucleophilic substitution reaction was used to introduce various nucleophiles in place of chlorine under different reaction conditions. The carbaldehyde group was oxidized by permanganate method and reduced with metallic sodium in methanol and ethanol. The synthesized compounds were characterized by UV-Vis, IR, and NMR. The antibacterial activity of the synthesized compounds was screened against two Gram-positive bacteria (Bacillus subtilis ATCC6633 and Staphylococcus aureus ATCC25923) and two Gram-negative bacteria (Escherichia coli ATCC 25922 and Pseudomonas aeruginosa ATCC 27853). Most of the compounds displayed potent activity against two or more bacterial strains. Among them, compounds 6 and 15 showed maximum activity against Pseudomonas aeruginosa with mean inhibition zones of 9.67 ± 1.11 and 10.00 ± 0.44 mm, respectively, while ciprofloxacin showed mean inhibition zone of 8.33 ± 0.44 mm at similar concentration. On the other hand, compound 8 exhibited maximum activity against Escherichia coli with inhibition zones of about 9.00 ± 0.55 mm at 300 μg/mL and 11.33 ± 1.11 mm at 500 μg/mL. The radical scavenging activity of these compounds was evaluated using 1,1-diphenyl-2-picryl hydrazyl (DPPH), and all of them displayed moderate antioxidant activity, with compound 7 exhibiting the strongest activity. The molecular docking study of the synthesized compounds was conducted to investigate their binding pattern with DNA gyrase, all of them were found to have minimum binding energy ranging from -6.0 to -7.33 kcal/mol, and the best result was achieved with compound 11. The findings of the in vitro antibacterial and molecular docking analysis demonstrated that the synthesized compounds have potential of antibacterial activity and can be further optimized to serve as lead compounds.
