• Bulletin of the Korean Chemical Society
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• 제23권5호
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• pp.769-772
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• 2002

• YAKHAK HOEJI
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• 제45권6호
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• pp.570-574
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• 2001

In order to discover new useful NSAIDs, novel N-substituted 1,2-benzisothiazoline-3-one 1,1- dioxide derivatives, which can exhibit potentially antiinflammatory activity were synthesized. 1,2-Benz-isothiazoline-3-one-N-acetic acids 6a, b were obtained from monochloroacetic acid and sodium 1,2-benz-isothiazoline-3-ones in DMF by N-alkylation reaction. N-Substituted 1,2-benzisothiazoline-3-one 1,1-dioxide derivatives 7a-e were synthesized through the coupling of compound 6a, b and several amines (aniline, 2- aminopyridine , 2-aminothiazole, 2-aminotetrazole) with dicyclohexylcarbodiimide in methyl e no chloride.

• YAKHAK HOEJI
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• 제31권6호
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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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• 제7권6호
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• pp.442-444
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• 1986

Starting with the readily available p-tert-butyl-calix[4]arene 2, tert-butyl groups are removed by $AlCl_3$-catalyzed de-alkylation reaction, and the calix[4]arene 3 formed is converted to the tetraacetate 4. This compound undergoes Fries rearrangement to yield p-acetylcalix[4]arene 6, which seems to be an attractive starting material for the introduction of functional groups. As a preliminary experiment p-(1-hydroxyethyl)calix[4]arene 7 is prepared by LiAlH$_4$ reduction of 6.

• Bulletin of the Korean Chemical Society
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• 제14권4호
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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 Life Science
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• 제15권3호
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• pp.332-336
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• 2005

Epoxide hydrolase activities of various microbial cells were analyzed by colorimetric assay based on alkylation of epoxides with 4-(p-nitrobenzyl)pyridine (NBP). The epoxide hydrolase activity was determined by measuring the decrease of color intensity at 560 nm due to the decrease of styrene oxide substrate by epoxide hydrolase-catalyzed hydrolysis reaction. The experimental conditions of NBP colorimetric assay were optimized for the efficient measurement of epoxide hydrolase activities from various microbial cells.

• Archives of Pharmacal Research
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• 제24권5호
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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.

• Archives of Pharmacal Research
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• 제25권1호
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• pp.11-24
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• 2002

The antitumor antibiotic (+)-CC-1065 can alkylate N3 of guanine in certain sequences. A previous high-field $^1H$ NMR study on the$(+)-CC-1065d[GCGCAATTG*CGC]_2$ adduct ($^*$ indicates the drug alkylation site) showed that drag modification on N3 of guanine results in protonation of the cross-strand cytosine [Park, H-J.; Hurley, L. H. J. Am. Chem. Soc.1997, 119,629]. In this contribution we describe a further analysis of the NMR data sets together with restrained molecular dynamics. This study provides not only a solution structure of the (+)-CC-1065(N3- guanine) DNA duplex adduct but also new insight into the molecular basis for the sequence- specific interaction between (+)-CC-1065 and N3-guanine in the DNA duplex. On the basis of NOESY data, we propose that the narrow minor groove at the 7T8T step and conformational kinks at the junctions of 16C17A and 18A19T are both related to DNA bending in the drugDNA adduct. Analysis of the one-dimensional $^1H$ NMR (in $H_2O$) data and rMD trajectories strongly suggests that hydrogen bonding linkages between the 8-OH group of the (+)-CC-1065 A-sub-unit and the 9G10C phosphate via a water molecule are present. All the phenomena observed here in the (+)-CC-1065(N3-guanine) adduct at 5'$-AATTG^*$are reminiscent of those obtained from the studies on the (+)-CC-1065(N3-adenine) adduct at $5'-AGTTA^*$, suggesting that (+)-CC-1065 takes advantage of the conformational flexibility of the 5'-TPu step to entrap the bent structure required for the covalent bonding reaction. This study reveals a common molecular basis for (+)-CC-1065 alkylation at both $5'-TTG^*$ and $5'-TTA^*$, which involves a trapping out of sequence-dependent DNA conformational flexibility as well as sequence-dependent general acid and general base catalysis by duplex DNA.

• Bulletin of the Korean Chemical Society
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• 제26권12호
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• pp.2021-2026
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• 2005

The oxidation of cytidine 1 and inosine 5 by sodium metaperiodate followed by the reaction of the product with $CH_3I$ in NaOH afforded 2',4'-dihydroxyhexopyranosyl derivatives 2 and 14 respectively. The reaction of thiophene-2-carboxylic acid or furfural with cytidine were taken place via cycloaddition afforded adducts 3 and 4 respectivily. The bromination of inosine 5 or its 2',3'-O-isopropylidine inosine 6 led to the formation of 8-bromoanalogue 7 and 8, respectively. The reaction of 8-bromo-2',3'-O-isopropylidine inosine (8) with ethylglycinate hydrochloride afforded 8-ethoxycarbonylmethylaminoinosine 9. The alkylation of the compound 6 with urea led to the formation of 3-carbonylaminoinosine 10. The oxidation of 6 with DCC afforded 4'-formyl derivative 11, which on reaction with ethyl glycinate hydrochloride followed by reaction with sodium cyanoborohydride afforded 12, while the treatment of dialdehyde inosine 13 with ethyl cyanoacetate in the presence of 0.5 N NaOH afforded compound 15.

• Bulletin of the Korean Chemical Society
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• 제34권9호
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• pp.2594-2596
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• 2013

Highly chemo- and regioselective reaction of hydroxybenzenes with ${\alpha},{\beta}$-unsaturated compounds in acidic ionic liquid l-butyl-3-methylimidazolium hydrogen sulphate ([BMIM]HSO4) was reported for the first time. A series of oxa-Michael adducts and Friedel-Crafts alkylated products were synthesized with good yields. The acidic ionic liquid could be easily recycled for at least 5 times with only minor loss in activity.