Novel Antimicrobial Iodo-Dihydro-Pyrrole-2-One Compounds

Abstract

Aim: A series of new hybrid molecules with two iodine atoms on the sides were synthesized. Methods: A one-pot, two-component method with trifluoroacetic acid as an effective catalyst to obtain dihydro-pyrrol-2-one compounds was developed. Short reaction times, a cheap catalyst, high yields and clean work-up are benefits of this method. Results: The chemical structures of the newly synthesized compounds were verified through spectroscopic techniques. Their antimicrobial activity against S. aureus, P. aeruginosa and C. albicans was tested in vitro. Conclusion: NC- and OH- radicals confer broad-spectrum antimicrobial activity, including against Gram-positive and Gram-negative bacteria and yeasts. Compounds 3g >7 and >9 were most active on the two bacterial species, while 3l >9 and >3i were most active against the fungal strain.

New Library of Iodo-Quinoline Derivatives Obtained by an Alternative Synthetic Pathway and Their Antimicrobial Activity

“…4-(1-(4-iodophenyl)-4-((4-iodophenyl)amino)-5-oxo-2,5-dihydro-1H-pyrrole-2-yl)benzonitrile 6f : [ 13 ]…”

“…5-(3,5-bis(trifluoromethyl)phenyl)-1-(4-iodophenyl)-3-((4-iodophenyl)amino)-1H-pyrrole-2(5H)-one 6g : [ 13 ]…”

“…The 1 H and 13 C NMR spectra recorded for this study were obtained for solutions in DMSO-d6 at 298 K on Bruker Avance NEO 400 and 600 MHz spectrometers, equipped with a 5 mm four nuclei direct detection z-gradient probe (H,C,F,Si-QNP) and 5 mm inverse detection multinuclear z-gradient probe, respectively, with solvent peaks as reference. All chemical shifts were reported in ppm (δ), and coupling constants (J) were reported in Hertz (Hz).…”

“…Both the coupling constants and chemical shift values are in agreement with this proposed vinylic group, indicating a trans proton configuration. The corresponding carbon atoms were identified in the 120-130 ppm interval in 13 C-NMR spectra, where double-bond carbon atoms usually resonate. Three-bond proton-carbon correlations identified in the HMBC spectrum support the covalent link of the ethylenic group with carboxy-quinoline and benzaldehyde cores.…”

“…In light of this, keeping with our quest for physiologically active hybrid heterocyclic molecules [ 10 , 11 ], as part of our concern for microbial active compounds [ 12 , 13 , 14 , 15 ], we present the synthesis of a library of novel iodine carboxy-quinoline derivatives as well as the resulting by-products. For this series of compounds, we looked at the influence of the electronic effects of the starting components and structure, and we evaluated the in vitro antibacterial activity.…”