1968-51-0Relevant academic research and scientific papers
Method for preparing 2-hydroxymethyl-3-alkoxy-4H-pyran-4-one by one-pot process
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Paragraph 0015, (2020/09/12)
The invention relates to a method for preparing 2-hydroxymethyl-3-alkoxy-4H-pyran-4-one by a one-pot process. The method is characterized by comprising the following steps: (1) dissolving pyromeconicacid with the concentration of 0.1-5 mol/L in a solvent, adding an alkali, controlling the molar ratio of pyromeconic acid to the alkali to be 1:(0.5-5), adding a formaldehyde aqueous solution with the weight percentage content of 20-50%, controlling the molar ratio of formaldehyde to pyromeconic acid to be (1-3):1, and reacting for 1-24 hours at the temperature of 0-100 DEG C; and (2) directly adding an alkylation reagent into step (1), controlling the molar ratio of the alkylation reagent to pyromeconic acid to be (1-3):1, and reacting at 10-100 DEG C for 1-24 hours. The method has the following advantages: on the basis of ensuring the reaction yield and the product quality, the separation of an intermediate is omitted, the operation steps are reduced, and the production period is shortened; and consumption of solvents and acid-base materials is reduced, and production cost is saved.
Preparation method of hydroxyl pyrone compound
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, (2020/07/12)
The invention provides a preparation method of 3-hydroxyl-2-(hydroxymethyl)-4H-pyran-4-one, and belongs to the field of pharmaceutical and chemical industry. The method comprises the following steps:reacting ethoxy pyran and ketone compounds with p-toluen
Synthesis method of 3-(benzyloxy)-4-oxo-4H-pyran-2-carboxylic acid
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, (2019/04/02)
The invention discloses a synthesis method of 3-(benzyloxy)-4-oxo-4H-pyran-2-carboxylic acid. The synthesis method takes furfuryl alcohol as a starting raw material and four-step reaction including rearrangement, addition, hydroxyl protection and oxidization is carried out; the total mol yield of a synthesis route is greater than 32 percent; the synthesis method has the characteristics of relatively moderate reaction conditions and the like, and the yield and purity of the 3-(benzyloxy)-4-oxo-4H-pyran-2-carboxylic acid are remarkably improved; meanwhile, the synthesis method has the advantagesof detailed technological operation steps, specific parameters, controllable conditions and stable technology, and can realize industrial large-batch production.
Basic 3-hydroxypyridin-4-ones: Potential antimalarial agents
Dehkordi, Lotfollah S.,Liu, Zu D.,Hider, Robert C.
, p. 1035 - 1047 (2008/09/20)
3-Hydroxypyridin-4-ones selectively bind iron under biological conditions and one such compound has found application in the treatment of thalassaemia-linked iron overload. Related molecules have also been demonstrated to possess an antimalarial effect at levels which are non-toxic to mammalian cells. In an attempt to improve the efficiency of such molecules we have investigated the effect of introducing basic nitrogen centres into 3-hydroxypyridin-4-ones in an attempt to achieve targeting to lysosomes and other intracellular acidic vacuoles. Several of the compounds reported in this communication possess enhanced antimalarial activity over that of the simple hydroxypyridinone class.
Orally active iron (III) chelators
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Page column 9, (2008/06/13)
A novel 3-hydroxypyridin-4-one compound of formula I is provided wherein R is hydrogen or a group that is removed by metabolism in vivo to provide the free hydroxy compound, R1 is an aliphatic hydrocarbon group or an aliphatic hydrocarbon group substituted by a hydroxy group or a carboxylic acid ester, sulpho acid ester or a C1-6 alkoxy, C6-aryloxy or C7-10aralkoxy ether thereof, R3 is selected from hydrogen and C1-6alkyl; and R4 is selected from hydrogen, C1-6alkyl and a group as described for R2; characterised in that R2 is selected from groups —CONH—R5??(i) —CH2NHCO—R5??(ii) —SO2NH—R5??(iii) —CH2NHSO2—R5??(iv) —CR6R6OR7??(v) —CONHCOR5??(viii) ?wherein R5 is selected from hydrogen and optionally hydroxy, alkoxy, or aralkoxy substituted C1-13 alkyl, aryl and C71-13 aralkyl, R6 is independently selected from hydrogen, C1-13 alkyl, aryl and C7-13 aralkyl, and R7 is selected from hydrogen, C1-13 alkyl, aryl and C7-13 aralkyl or a pharmaceutically acceptable salt of any such compound with the proviso that when R7 is hydrogen, R6 is not selected from aryl and with the proviso that the compound is not 1-ethyl-2-(1′-hydroxyethyl)-3-hydroxypyridin-4-one.
Synthesis, physicochemical characterization, and biological evaluation of 2-(1'-hydroxyalkyl-3-hydroxypyridin-4-ones: Novel iron chelators with enhanced pFe3+ values
Liu, Zu D.,Khodr, Hicham H.,Liu, Ding Y.,Lu, Shu L.,Hider, Robert C.
, p. 4814 - 4823 (2007/10/03)
The synthesis of a range of 2-(1'-hydroxyalkyl)-3-hydroxypyridin-4-ones as bidentate iron(III) chelators with potential for oral administration is described. The pK(a) values of the ligands and the stability constants of their iron(III) complexes have been determined. Results indicate that the introduction of a 1'-hydroxyalkyl group at the 2-position leads to a significant improvement in the pFe3+ values. Such an effect was found to be greater with the hydroxyethyl substituent than with the hydroxy-methyl substituent, particularly in the cases of 1-ethyl-2(1'-hydroxyethyl)-3- hydroxypyridin-4-one (pFe3+ = 21.4) and 1,6-dimethyl-2-(1'-hydroxyethyl)3- hydroxypyridin-4-one (pFe3+ = 21.5) where an enhancement on pFe3+ values in the region of two orders of magnitude is observed, as compared with Deferiprone (1,2-dimethyl-3-hydroxypyridin-4-one) (pFe3+ = 19.4). The ability of these novel 3-hydroxypyridin-4-ones to facilitate the iron excretion in bile was investigated using a [59Fe] ferritin-loaded rat model. Chelators and prodrug chelators possessing high pFe3+ values show great promise in their ability to remove iron under in vivo conditions.
