5753-96-8Relevant articles and documents
Substituted 2-hydroxy-1,2-dihydropyrrol-3-ones: Fluorescent markers pertaining to oxidative stress and aging
Chen, Peng,Wiesler, Donald,Chmelik, Josef,Novotny, Milos
, p. 970 - 979 (1996)
Previous observations that the aging process correlates with occurrence of certain fluorescent biological pigments have led to numerous efforts in elucidating the chemical nature of the fluorophores generated through reactions of primary amines and various products of lipid peroxidation. In this study, model reactions of saturated aldehydes with aliphatic amines in the presence of peroxides were found to generate structurally unusual fluorescent compounds. Substitution of a lysine-containing peptide for simpler amines has also yielded similar fluorescence. The spectral excitation and emission maxima (around 360 and 430 nm, respectively) of these fluorophores match those widely reported in peroxidized biological objects. The fluorescent compounds in our model studies have been chromatographically isolated and their structures determined through mass spectrometry, NMR spectrometry, and Fourier-transform infrared spectroscopy. The spectrometric data indicate the fluorescent products to be alkylated 2- hydroxy-1,2-dihydropyrrol-3-ones, obtained by the action of 1,2,4-triketone intermediates upon the primary amines. Independent syntheses of several 1,2,4-triketones were carried out. One such triketone reacted with hexylamine to form a fluorescent compound spectroscopically identical to the fluorescent reaction product of hexanal, hydrogen peroxide, and hexylamine.
Quinoxaline-benzimidazole rearrangements in the reactions of 3-alkanoylquinoxalin-2-ones with 1,2-phenylenediamines
Kalinin,Isaikina,Mamedov
, p. 1307 - 1314 (2007)
The interaction of 3-alkanoylquinoxalin-2-ones with 1,2-phenylenediamines in boiling acetic acid led to the contraction of the pyrazine ring as the result of a quinoxaline-benzimidiazole rearrangement with the formation of 2-benzimidazolyl-substituted quinoxalines.
Asymmetric Transfer Hydrogenation of α-Keto Amides; Highly Enantioselective Formation of Malic Acid Diamides and α-Hydroxyamides
Gediya, Shweta K.,Vyas, Vijyesh K.,Clarkson, Guy J.,Wills, Martin
supporting information, p. 7803 - 7807 (2021/10/20)
The asymmetric transfer hydrogenation (ATH) of α-keto-1,4-diamides using a tethered Ru/TsDPEN catalyst was achieved in high ee. Studies on derivatives identified the structural elements which lead to the highest enantioselectivities in the products. The α-keto-amide reduction products have been converted to a range of synthetically valuable derivatives.
Design, synthesis, and evaluation of alkyl-quinoxalin-2(1h)-one derivatives as anti-quorum sensing molecules, inhibiting biofilm formation in aeromonas caviae Sch3
Bl?cher, René,Ramírez, Ariel Rodarte,Castro-Escarpulli, Graciela,Curiel-Quesada, Everardo,Reyes-Arellano, Alicia
, (2018/11/30)
With the increasing antibiotic resistance of bacterial strains, alternative methods for infection control are in high demand. Quorum sensing (QS) is the bacterial communication system based on small molecules. QS is enables bacterial biofilm formation and pathogenic development. The interruption of QS has become a target for drug discovery, but remains in the early experimental phase. In this study, we synthesized a set of six compounds based on a scaffold (alkyl-quinoxalin-2(1H)-one), new in the anti-QS of Gram-negative bacteria Aeromonas caviae Sch3. By quantifying biofilm formation, we were able to monitor the effect of these compounds from concentrations of 1 to 100 μM. Significant reduction in biofilm formation was achieved by 3-hexylylquinoxalin-2(1H)-one (11), 3-hexylylquinoxalin-2(1H)-one-6-carboxylic acid (12), and 3-heptylylquinoxalin-2(1H)-one-6-carboxylic acid (14), ranging from 11% to 59% inhibition of the biofilm. This pilot study contributes to the development of anti-QS compounds to overcome the clinical challenge of resistant bacteria strains.
