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Synthesis of selenowogonin : potential antioxidant and neuroprotective agent

Other Titles
 셀레노우고닌의 합성 
Issue Date
Dept. of Pharmacy/석사
Selenium was discovered by Jons Jacob Berzelius in 1817. Back then, it had been considered as a poisonous element because the consumption of excessive amounts of selenium caused diverse diseases in animals. However, the bright side of selenium was noticed when two bacterial enzymes, formate dehydrogenase and glycine reductase reductase, were reported to contain selenium in 1973. Moreover, selenium is found to be involved in part of the active site of the antioxidant enzyme glutathione peroxidase. The glutathione peroxidase catalyzes the reduction of reactive oxygen species (ROS) at the expense of GSH as a reductant, thereby protecting various organisms from oxidative damage. In 1987, it was reported that ebselen, an organoselenium compound, has an antioxidant mechanism similar to glutathione peroxidase. The compounds with similar mechanism of glutathione peroxidase have been developed, therefore, by modifying the structure of ebselen. Wogonin is a flavonoid derived from the root of Scutellaria baicalensis Georgi, a medicinal plant traditionally used in oriental medicine. Since microglia-mediated inflammatory responses play an important pathogenic role, the wogonin exert anti-inflammatory and neuroprotective effects on brain microglia against brain injury. Yet its polarity makes it difficult to pass through brain-blood barrier, which limits the possibilities of the use of drugs The study of this thesis was focused on synthesizing seleno-heterocyclic compounds, to have more non-polar properties. The non-polar property was increased by substituting oxygen with selenium in the heterocyclic compound. Selenowogonin was expected to maximize the anti-inflammatory and neuroprotective effects by increasing the amounts of compound passed through the membrane. The starting material, 4-methoxyphenol was synthesized to the precursor, (3-Bromo-2,5-dimethoxyphenoxy) (tert-butyl)dimethylsilane throughout the conversion of functional groups, as well as Friedel-Crafts acylation. The precursor was cyclized with selenium in heating condition. In conclusion, seleno-norwogonin, the demethylated compound in all position was obtained.
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1. College of Medicine (의과대학) > Others (기타) > 5. Others
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