1016582-77-6Relevant articles and documents
Design, synthesis and biological evaluation of a series of iron and copper chelating deferiprone derivatives as new agents active against Candida albicans
Bortolami, Martina,Pandolfi, Fabiana,Messore, Antonella,Rocco, Daniele,Feroci, Marta,Di Santo, Roberto,De Vita, Daniela,Costi, Roberta,Cascarino, Paola,Simonetti, Giovanna,Scipione, Luigi
, (2021/05/13)
Candida albicans, in specific conditions, is responsible of severe invasive systemic candidiasis that are related to its ability to produce biofilm on biological and artificial surfaces. Many studies reported the role of iron in fungal growth and virulence and the ability of metal chelating agents to interfere with C. albicans metabolism, virulence and biofilm formation. Here we report the activity of 3-hydroxy-1,2-dimethyl-4(1H)-pyridinone (deferiprone) derivatives against C. albicans planktonic cells and biofilm. Some of the studied compounds (2b and 3b) were able to chelate Fe(III) and Cu(II), and showed an interesting activity on planktonic cells (MIC50 of 32 μg/mL and 16 μg/mL respectively) and on biofilm formation (BMIC50 of 32 μg/mL and 16 μg/mL respectively) in cultured ATCC 10,231C. albicans; this activity was reduced, in a concentration dependent way, by the addition of Fe(III) and Cu(II) to the culture media. Furthermore, the most active compound 3b showed a low toxicity on Galleria mellonella larvae.
Physical and structural studies of N-substituted-3-hydroxy-2-methyl-4(1H)-pyridinones
Nelson, William O.,Karpishin,Timothy B.,Rettig, Steven J.,Orvig, Cris
, p. 123 - 131 (2007/10/02)
A series of 3-hydroxy-2-methyl-4(1H)-pyridinones has been prepared with the sunstituents H, CH3, n-C6H11, and CH2CH2NH2 at the ring N.The dipyridinone 1,6-bis(3-hydroxy-2-methyl-4(1H)-pyridinon-1-yl)hexane has also been synthesized.The products with H and CH3 subtituents have been studied by single crystal X-ray diffraction.Crystals of 3-hydroxy-2-methyl-4-pyridinone are monoclinic, a=6.8351(4), b=10.2249(4), c=8.6525(4) Angstroem, β=105.215(4) deg, Z=4,space group P21/n and those of 3-hydroxy-1,2-dimethyl-4-pyridinone are orthorhombic, a=7.3036(4), b=13.0490(6), c=13.7681(7) Angstroem, Z=8, space group Pbca.Both structures were solved by direct methods and were refined by full-matrix least-squares procedures to R=0.037 and 0.044 for 914 and 857 reflections with I>/=3?(I), respectively.Bond lengths and angles in the compounds were normal.All the compounds have been studies by mass spectrometry, and by infrared and proton nmr spectroscopies.The importance of hydrogen bonding to both the solution and solid state properties of these compounds has been confirmed by these techniques.
