203863-45-0Relevant academic research and scientific papers
Method for resolving racemic mixtures of 5-substituted 4-hydroxy-2-furanones
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, (2008/06/13)
This invention affords a solution to the technical problem of obtaining one or both enantiomers of 5-substituted 4-hydroxyfuran-2-ones in pure form by resolution with enantiomerically pure bases. Racemic mixtures of 5-substituted 4-hydroxy-2(5H)-furanones, including 5-substituted and 5,5-disubstituted, 4-hydroxy and 3,4-dihydroxy furanones are separated into pure enantiomers by crystallization with an enantiomerically pure base, such as cinchonidine. In specific solvent mixtures, for example, 95% ethanol, the diastereomerically pure salt of one enantiomer crystallizes. The enantiomerically pure furanone can then be obtained simply by filtration and treatment of the salt with an acid, for example, trifluoracetic acid, followed by precipitation with water, filtration and drying. Moreover, the other enantiomer may be equally obtained in pure form by evaporation of the mother liquor, followed by the same treatment of the salt as described before.
5,5-Disubstituted-3, 4-dihydroxy-2(5H)-furanones and methods of use therefor
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, (2008/06/13)
The present invention relates to synthetic methods for the production of both optically active and racemic 5,5-disubstituted-3,4-dihydroxy-2(5H)-furanones; 5-[(4-aryl)-3-butynyl]-3,4-dihydroxy-2(5H)-furanones; 5-(2-arylthio)ethyl-3,4-dihydroxy-2(5H)-furanones; and 5-(2-aryloxy)ethyl-3,4-dihydroxy-2(5H)-furanones. This invention further relates to the use of the above mentioned compounds as anti-inflammatory agents through their action as mixed inhibitors of lipid peroxidation, 5-lipoxygenase, cyclooxygenase-1 and cyclooxygenase-2. The invention further relates to the use of such compounds in the treatment of chronic inflammatory disorders such as asthma, rheumatoid arthritis, inflammatory bowel disease, atherosclerosis, acute respiratory distress syndrome, and central nervous system disorders such as Alzheimer's and Parkinson's disease wherein reactive oxygen species and inflammatory mediators are contributing deleterious factors.
