22105-10-8Relevant academic research and scientific papers
3-Hydroxy-(4H)-benzopyran-4-ones as potential iron chelating agents in vivo
Ferrali, Marco,Donati, Donato,Bambagioni, Sabrina,Fontani, Marco,Giorgi, Gianluca,Pietrangelo, Antonello
, p. 3041 - 3047 (2007/10/03)
Increasing evidence suggests that iron plays an important role in tissue damage both during chronic iron overload diseases (i.e., hemochromatosis) and when, in the absence of actual tissue iron overload, iron is delocalised from specific carriers or intracellular sites (inflammation, eurodegenerative diseases, post-ischaemic reperfusion, etc.). In order to be used for therapeutical purposes in vivo, a reliable iron chelator should be capable of preventing the undesired effects that follow the electrochemical activation of iron (see below). Bearing in mind the molecular structure of some flavonols that are able to chelate iron, we synthesised a new oral iron-chelator, 2-methyl-3-hydroxy-4H-benzopyran-4-one (MCOH). We demonstrate that MCOH chelates iron in a 2:1 ratio showing a stability constant of ～1010. MCOH is able to cross cell membranes (erythrocytes, ascite tumour cells) in both directions. Following intraperitoneal administratio to rats, it is quickly taken up by the liver and excreted in the urine withi 24 h. A similar behaviour has bee documented after oral administration. We propose that MCOH may represent the prototype of a new class of iron chelating agents to be developed for iron-removal therapy in vivo with the goal of preventing tissue damage caused by the iron redox cycle. Copyright
Studies in the chemistry of chromone epoxides
Donnelly, John A.,Keegan, John R.,Quigley, Killian
, p. 1671 - 1680 (2007/10/02)
Chromones and isoflavones, but not flavones, were epoxidized by alkaline hydrogen peroxide. 3-Substituted chromone epoxides were considerably more stable than others; one isoflavone epoxide was converted into a fluorohydrin, another into a 1,2-diol. The latter is a 2-hydroxychromanone and a similarly structured compound was obtained by the cyclisation of 2'-benzoyloxy-2,2-dibromoacetophenone. Acid-catalysed ring-opening of chromone epoxides occurred regioselectively yielding 3-hydroxychromanones. Base-catalysed ring-opening also occurred regioselectively but at the 3-position. Acid- and base-catalysed hydrolysis of 2-methy-lisoflavone epoxide resulted in cleavage of both heterocyclic rings, yielding, respectively, a 1,3- and a 1,2-diketone. This epoxide formed a cyclic sulphate with sulphuric acid.
