• Bulletin of the Korean Chemical Society
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• v.30 no.7
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• pp.1463-1469
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• 2009

Eleven novel oxiranyl and thiiranyl phenolic compounds were synthesized as potential antitumor agents using epichlorohydrin and epithiohydrin in the presence of $K_2CO_3$. Cytotoxicities were found in range of I$C_{50}$ values of 2.5-14.8 $\mu$M, which was partially attributed to topoisomerase II inhibition. Bis-thiiranyl anthraquinone analog, 19 showed more cytotoxicity against MDA-MB-231 (breast cancer cell) and PC3 (prostate cancer cell) after 24 and/or 48 h and more potent topoisomerase II inhibitory activity than etoposide.

• Bulletin of the Korean Chemical Society
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• v.30 no.7
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• pp.1531-1534
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• 2009

(2S,3R)-3-Hydroxy-2-(hydroxymethyl)-3,6-dihydro-2H-pyridine 8, an important precursor for the synthesis of polyhydroxylated piperidine azasugars, has been prepared from L-serine. Highly stereoselective nucleophilic addition to amino aldehyde 5 gave the corresponding allylic alcohol 6 which proceeded to give dihydro-2H-piridine 7a via a Grubbs II catalyzed RCM. Stereoselective H-bond directed epoxidation of allylic alcohol led to the oxiranyl alcohol 9 which was easily converted to L-deoxyaltronojirimycin by regioselective ring opening.

• YAKHAK HOEJI
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• v.56 no.1
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• pp.42-47
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• 2012

Soluble epoxide hydrolase (sEH) is a metabolic regulator of epoxyeicosatrienoic acids (EETs). EETs have many beneficial effects, vasodilation, anti-diabetes, anti-inflammation, cardiovascular protection, renal protection. Therefore, selective sEH inhibitors have a potential for treating these diseases. In the present study, screening methods for sEH inhibitors using PHOME ((3-phenyl-oxiranyl)-acetic acid cyano-(6-methoxynaphthalen-2-yl)-methyl ester) and 14-15-EET as substrates were established. To determine selectivity, microsomal epoxide hydrolase (mEH) inhibition assay was also developed using styrene oxide as a substrate of microsomal epoxide hydrolase. Our results obtained from 12-[[(tricyclo[3.3.1.13,7]dec-1-ylamino)carbonyl]amino]-dodecanoic acid (AUDA) used as a positive sEH inhibitor and valpromide used as a positive mEH inhibitor showed that these methods are useful for discovery of drug candidates.