• Bulletin of the Korean Chemical Society
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• v.14 no.4
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• pp.481-485
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• 1993

Dialkyl 1-bromobenzene-2,6-diacetates were easily prepared by the carbonylation of the moiety of benzylic bromide in 1-bromo-2,6-bis(bromomethyl)benzene with alcohol in the presence of NaOAc< TEX>${\cdot}$3H$_2$O and a catalytic amount of Co$_2$(CO)$_8$under the atmospheric pressure of carbon monoxide at room temperature in excellent yield. Alkyl 2,6-bis(alkoxymethyl)benzoates were obtained by the carbonylation of the moiety of aryl bromide in 1-bromo-2,6-bis(alkoxymethyl)-benzene, which derived from 1-bromo-2,6-bis(bromomethyl)benzene, alcohol, NaOR, and CH$_3$I under the same conditions. Alkyl 2,6-bis(carboxymethyl)benzoate was also obtained in a trace amount for 24 hrs at room temperature.

• Bulletin of the Korean Chemical Society
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• v.22 no.11
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• pp.1264-1266
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• 2001

• Journal of the Korean Chemical Society
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• v.33 no.6
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• pp.673-676
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• 1989

• Archives of Pharmacal Research
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• v.8 no.1
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• pp.39-41
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• 1985

Bromocycloetherification of a series of 3-and 4-olefinic alcohols using NBS-acetonitrile gave corresponding bromo-tetrahydrofuran with high regio and steroselectivity.

• Proceedings of the PSK Conference
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• 2003.04a
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• pp.236.1-236.1
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• 2003

Bromofluoroacetophenone derivatives which produce fluorine substituted phenyl radicals that cleave DNA upon excitation were investigated as a novel photonuclease. Pyrrolecarboxamide-conjugated bromofluoroacetophenones: 4'-bromo-2'-fluoroacetophenone and 2' -bromo-4'-fluoroacetophenone were synthesized and their DNA cleaving activities and sequence selectivities were determined. (omitted)

• Journal of the Korean Chemical Society
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• v.35 no.2
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• pp.165-171
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• 1991

The electrochemical reduction of carbon-6-dibromo groups on 6,6-dibromo penicillanic acid 1,1-oxide(DBPA) was investigated by direct current, differential pulse polarography, cyclic voltammetry and controlled potential coulometry. The irreversible two electrons transfer on the reductive debromination of each bromo group proceeded by EC,EC mechanism at the two electrode reduction steps(-0.48, -1.62 volts). The 6-bromo-PA and 6,6-dihydro-PA was synthesized by controlled potential electrolysis. Upon the basis of results on the products analysis and interpretation of polarograms obtained at various pH, electrochemical reaction mechanism was suggested.

• Biomolecules & Therapeutics
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• v.15 no.2
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• pp.95-101
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• 2007

Resveratrol (3,5,4’-trihydroxy-trans-stilbene), a naturally occurring phytoallexin abundant in grapes and several plants, has been shown to be active in inhibiting proliferation and inducing apoptosis in several human cancer cell lines. On the line of the biological activity of resveratrol, a variety of resveratrol analogs were synthesized and evaluated for their growth inhibitory effects against several human cancer cell lines. In the present study, we found that one of the resveratrol analogs, 3,4,5-trimethoxy-4’-bromo-cis-stilbene, markedly suppressed human colon cancer cell proliferation (EC$_{50}$ = 0.01 ${\mu}$g/ml), and the inhibitory activity was superior to its corresponding trans-isomer (EC$_{50}$ = 1.6 ${\mu}$g/ml) and resveratrol (EC$_{50}$ = 18.7 ${\mu}$g/ml). Prompted by the strong growth inhibitory activity in cultured human colon cancer cells (Col2), we investigated its mechanism of action. 3,4,5-Trimethoxy-4’-bromo-cis-stilbene induced arrest of cell cycle progression at G2/M phase and increased at sub-G1 phase DNA contents of the cell cycle in a time- and dose-dependent manner. Colony formation was also inhibited in a dose-dependent manner, indicating the inhibitory activity of the compound on cell proliferation. Moreover, the morphological changes and condensation of the cellular DNA by the treatment of the compound were well correlated with the induction of apoptosis. These data suggest the potential of 3,4,5-trimethoxy-4’-bromo-cis-stilbene might serve as a cancer chemotherapeutic or chemopreventive agent by virtue of arresting the cell cycle and inducing apoptosis for the human colon cancer cells.

• Journal of the Korean Chemical Society
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• v.39 no.5
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• pp.414-420
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• 1995

$\alpha$-Bromo-$\omega$-fluoroalkanes are synthesized in 19∼55% yields from the reactions of dibromoalkanes with AgF and TBABr in acetonitrile at $82^{\circ}C$ for 20 minutes. The reaction is monitored with gas-chromatography. 1^H$ NMR and $19^F$ NMR-Spectrometer are used for identification of $\alpha$-Bromo-$\omega$-fluoroalkanes, difluoroalkane, fluoroalken and bromoalkene.

• Bulletin of the Korean Chemical Society
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• v.26 no.6
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• pp.989-992
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• 2005

Dynamic kinetic resolution of $\alpha$-bromo carboxylic acid derivatives in nucleophilic substitution with chiral $\alpha$-amino ester nucleophiles in the presence of TBAI and DIEA has been investigated for stereoselective syntheses of 1,1'-iminodicarboxylic acid derivatives. Nucleophilic substitutions with various chiral $\alpha$-amino esters gave iminodiacetates 2-8 with stereoselectivities up to 87 : 13 dr. Also, the reactions of N-($\alpha$-bromo-$\alpha$-phenylacetyl)-L-alanine methyl ester with L-alanine, D-alanine and glycine methyl ester nucleophiles afforded N-carboxyalkyl dipeptide analogues 10-12 up to 90 : 10 dr.

• Macromolecular Research
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• v.12 no.1
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• pp.63-70
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• 2004

We have synthesized various types of poly(ethylene glycol) (PEG)-ibuprofen conjugates by the nucleophilic substitution of bromo-terminated PEG with ibuprofen-Cs salt; PN (Pluronic) was also used in place of PEG. All the bromo-terminated PEGs and PN were obtained in high yield. Conversions of the terminal hydroxyl groups to bromo-termini were quantitative, as were the drug conjugation processes. The Ι$_1$/Ι$_3$values obtained from solutions of the ibuprofen-conjugated prodrugs are summarized in relation to those of ibuprofen in water and in aqueous solutions of the original PEG, PN, and several ordinary surfactants. We believe that the fully hydrophilic PEG is completely hydrated and forms no hydrophobic pocket by segment aggregation. These results indicate that the probe environment is significantly hydrophobic, particularly in the solution of prodrug PN, for which the ratio is similar to that obtained from typical micelles of surfactants. The results suggest, therefore, that the present synthetic method is very useful for preparing PEG-based prodrugs from pharmaceuticals having carboxyl functionalities.