• YAKHAK HOEJI
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• v.31 no.6
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• pp.370-375
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• 1987

1, 4-Benzodiazepin 5-one was prepared from 2-aminobenzamide derivatives by acid catalyzed intermolecular cyclization. N-Alkylation of 2-aminobenzamide with $\alpha$-bromo acetaldehyde diethylacetal to 2(2', 2'-diethoxyethyl) aminobenzamide (I) and subsequent treatment of I with acid gave 1, 4-benzdiazepin 5-one, where as the acetyl derivatives of I did not react to 1, 4-benzodiazepin 5-one but to methyl 4-quinazolone (IV).

• Bulletin of the Korean Chemical Society
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• v.14 no.4
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• pp.449-452
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• 1993

o-Aminophenols react with alcohols in the presense of a catalytic amount of ruthenium catalyst at 180$^{\circ}C$ to give 2-substituted benzoxazole in good yield. The yields of 2-substituted benzoxazoles were affected by the yield of N-alkylation compound from o-aminophenol and alcohol as starting materials. During the reaction, a stoichiometric amount of hydrogen was spontaneously evolved into the gas phase.

• Journal of the Korean Applied Science and Technology
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• v.3 no.1
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• pp.65-71
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• 1986

Four amphoteric surfactants, 1-(N-alkyl-N,N-dimethyl ammonio)-4-naphthalene sulfonates, were prepared by the alkylation of 1-(N,N-dimethylamino)-4,naphthalene sulfonic acid with chloroalkanes such as 1-decylchloride, 1-tetradecyl chloride and 1-hexadecyl chloride. These quaternary ammonium compounds such as 1-(N-decyl-N, N-dimethylammonio)-4-naphthalene sulfonate, 1-(N-dodecyl-N,N-dimethylammonio)-4-naphthalene sulfonate, 1-(N-tetradecyl-N,N-dimethylammonio)-4-naphthalene sulfonate and 1-(N-hexadecyl-N,N-dimethylammonio)-4-naphthalene sulfonate could be separated by means of thin layes chromatography and column chromatography. The surface chemical properties such as surface tension, foaming power, foam stability, wetting efficiency and solubilizing effect for these four compounds were measured. Also critical micelle concentration and hydrophilic-lipophilic balance(HLB) were evaluated. These compounds showed good surface as O/W type emulsifying agent and detergent.

• Bulletin of the Korean Chemical Society
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• v.32 no.5
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• pp.1511-1518
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• 2011

A series of 1,4-disubstituted octahydroquinoxaline-2,3-dione derivatives was prepared through two steps reaction. The latter involves the formation of N,N-disubstituted cyclohexane-1,2-diamine derivatives (la-j) through reductive alkylation of 1,2-cyclohexanediamine with different aldehydes in presence of sodium cyanoborohydride. Fusion of compounds (1a-j) with diethyl oxalate affording the target compounds (2a-j). Elucidation of structures of compounds (2a-j) was based upon different spectral data as well as the elemental methods of analyses. In addition, mass spectrometry and X-ray diffraction analyses were carried out. Moreover, the lipophilicity of the target compounds as expressed from the Clog P. Most of the test compounds (2a-j) showed weak to moderate antibacterial and antifungal activities against most of the used bacterial and fungal strains in comparison to chloramphenicol and clotrimazole as reference drugs respectively.

• YAKHAK HOEJI
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• v.30 no.5
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• pp.238-244
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• 1986

As one of the starting materials, methylthioacetyl chloride(7) was synthesized in fair yield from mercaptoacetic acid via methyl methylthioacetate(5) prepared by alkylation employing N, N'-dicyclohexyl-O-methylisourea(4). Then 1-$\beta$-D-arabinofuranosylcytosine-5'-methylthioacetate (3) was prepared by esterification of ara-C with obtained methylthioacetyl chloride and tested for inhibitory activity on DNA synthesis in the growing primary hepatocytes and hepatoma strains($H_4$-II-E and HTC cells). In these in vitro cell lines, the inhibitory effect of ara-C-MTA(3) on DNA synthesis was similar to that of its parent ara-C but slightly lower.

• Bulletin of the Korean Chemical Society
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• v.12 no.1
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• pp.26-31
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• 1991

Facile and efficient syntheses of terpenic perfumeries cis-jasmone, dihydrojasmone, and tetrahydrojasmone have been investigated. Cis-jasmone was synthesized by successive metallation followed by alkylation of acetone N,N-dimethylhydrazone with (Z)-2-penten-1-yl tosylate (or 2-pentyn-1-yl tosylate) and propylene oxide in one flask to give a ketonic alcohol, which was oxidized to the corresponding diketone, followed by base-catalyzed intramolecular aldol condensation to give a regioselective cyclization product. Dihydrojasmone and tetrahydrojasmone could be conveniently obtained from 2-octanone. The dimethylhydrazone of the ketone was lithiated with butyllithium and reacted with propylene oxide to give a ketonic alcohol, which was oxidized to a diketone, followed by base-catalyzed intramolecular cyclization to afford dihydrojasmone. Tetrahydrojasmone was prepared by converting the ketonic alcohol into corresponding iodoketone, followed by base-catalyzed intramolecular cycloalkylation to furnish an odoriferous product.

• The Korean Journal of Nuclear Medicine
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• v.39 no.4
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• pp.215-223
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• 2005

Current interest in the regioselective N-functionalization of tetraazacycloalkanes (cyclen and cyclam) stems mainly from their complexes with radioactive metals for applications in diagnostic ($^{64}Cu,\;^{111}In,\;^{67}Ga$) and therapeutic ($^{90}Y$) medicine, and with paramagnetic ions for magnetic resonance imaging ($Gd^{+3}$). Selective methods for the N-substitution of cyclen and cyclam is a crucial step in most syntheses of cyclen and cyclam-based radiometal complexes and bifunctional chelating agents. In addition, mixing different pendent groups to give hetero-substituted cyclen derivatives would be advantageous in many applications for fine-tuning the compound's physical properties. So far, numerous approaches for the regioselective N-substitution of tetraazacycloalkanes and more specifically cyclen and cyclam are reported. Unfortunately, none of them are general and every strategy has its own strong points and drawbacks. Herein, we categorize numerous regioselective N-alkylation methods into three strategies, such as 1) direct substitution of the macrocycle, 2) introductiou of the functional groups prior to cyclization, and 3) protection/iunclionallrationideproteclion. Our discussion is also split into the methods of mono- and tri-functionalization and di-functionalizataion based on number of substituents. At the end, we describe new trials for the new macrocycles which iorm more stable metal complexes with various radiometals, and briefly mention the commercially available tetraazacycloalkanes which are used for the biconjugation of biomolecules.

• Bulletin of the Korean Chemical Society
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• v.14 no.2
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• pp.234-238
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• 1993

The method of study describes the determination of the nanogram amounts of mono-, di-, and tri-butyltin compounds in sea water. The procedure is based on 1) the conversion of tin compounds to non-ionic species by sodium tetraethyl borate as an alkylation reagent, 2) one-step ethylation and 3) extraction. No further purification or concentration of the extract was required before GC-FPD (Flame Photometric Detector). The detection limits for mono-, di- and tri-butyltin were 12.50, 6.02, and 4.19 ng/L. The linear range (0-120 ng/L) was solely dependent on the detector response height. Sea water samples (n=24) were obtained from Masan Bay, Busan, Ullsan, Gunsan, Sockcho, Yeasu, Donghae, Inchun, Kanghwa, and Ahsan in Korea. The samples were collected between June, 1992 to July, 1992 and the distribution of monobutyltintrichloride (MBTC), dibutyltindichloride (DBTC), and tributyltinchloride (TBTC) in sea water was recorded. The concentrations of butyltin compounds in seawater were found to be in the range of N.D. (not detected)-61.93 ng/L for MBTC, N.D.-32.16 ng/L for DBTC, and N.D.-55.76 ng/L for TBTC.

• Archives of Pharmacal Research
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• v.24 no.5
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• pp.455-465
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• 2001

The highly potent cytotoxic DNA-DNA cross-linker consists of two cyclopropa[c]pyrrolo[3,4-3]indol-4(5H)-ones insoles [(+)-CPI-I] joined by a bisamido pyrrole (abbreviated to "Pyrrole"). The Pyrrole is a synthetic analog of Bizelesin, which is currently in phase II clinical trials due to its excellent in vivo antitumor activity. The Pyrrole has 10 times more potent cytotoxicity than Bizelesin and mostly form DNA-DNA interstrand cross-links through the N3 of adenines spaced 7 bp apart. The Pyrrole requires a centrally positioned GC base pair for high cross-linking reactivity (i.e., $5^1$-T$AT_2$A*-$3^1$), while Bizelesin prefers purely AT-rich sequences (i.e., $5^1$-T$AT_4$A*-$3^1$, where /(equation omitted) represents the cross-strand adenine alkylation and A* represents an adenine alkylation) (Park et al., 1996). In this study, the high-field $^1$H-NMR and rMD studies are conducted on the 1 1-mer DNA duplex adduct of the Pyrrole where the 5′(equation omitted)TAGTTA*-3′sequence is cross-linked by the drug. A severe structural perturbation is observed in the intervening sequences of cross-linking site, while a normal B-DNA structure is maintained in the region next to the drug-modified adenines. Based upon these observations, we propose that the interplay between the bisamido pyrrole unit of the drug and central C/C base pair (hydrogen-bonding interactions) is involved in the process of cross-linking reaction, and sequence specificity is the outcome of those interactions. This study suggests a mechanism for the sequence specific cross-linking reaction of the Pyrrole, and provides a further insight to develop new DNA sequence selective and distortive cross-linking agents.

• Journal of the Korean Chemical Society
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• v.39 no.7
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• pp.564-571
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• 1995

5-Amino-2H-1,2,4-thiadiazoline-3-one has been prepared from 2-thiobiuret through a oxidative cyclization under basic hydrogen peroxide condition. Lactam-lactim tautomerism of 5-amino-2H-1,2,4-thiadiazoline-3-one has been examined by spectroscopic methods and ab initio molecular orbital calculation. These results were shown that 5-amino-2H-1,2,4-thiadiazoline-3-one exists as lactam form. Reaction conditions for alkylating 5-amino-2H-1,2,4-thiadiazoline-3-one with alkyl halides in the presence of various bases were studied in DMF and $H_2O$-THF two phase system. $Li_2CO_3$ base in DMF method gave best result in this investigation. The alkylation has been taken place at N-2 position. The identification of the product is confirmed by spectral data of IR, $^1H$ NMR and $^13C$ NMR and the comparison of authentic sample, 5-amino-2-methyl-1,2,4-thiadiazolidine-3-one, obtained from the oxidative cyclization of 5-methyl-2-thiobiuret.