• Archives of Pharmacal Research
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• 제21권2호
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• pp.187-192
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• 1998

The cis- and trans-diastereomers of the 7,8-dihydro-7-deazapurine derivatives were synthesized from the corresponding diastereomers of 4-tran5-cyano-2-methyl-3-phenyl-5-oxopyrrolidine (5), which were reduced from the 2-cis- and 2-tran5-diastereomers of 4-trans-cyano-2-hydroxymethyl-3-phenyl-5-oxopyrrolidine (2) via tosylation, iodination and following elimination respectively. The prepared cis- and ttans-diastereomers of 6-amino-2-mercapto-8-methyl-7-phenyl-7,8-dihydro-7(9H)-deazapurine (8) were transferred to the corresponding 2-methylthio-diastereomers 9 and following desulfurization with Raney-nickel leaded to the cis and trans-diastereomers of 6-amino-8-methyl-7-phenyl-7,8-dihydro-7(9H)-deazapurine (10), respectively. The synthesized 7-deazapurine derivatives were tested for their antibiotic activity by the serial two-fold dilution method.

• Bulletin of the Korean Chemical Society
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• 제33권2호
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• pp.681-684
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• 2012

• Bulletin of the Korean Chemical Society
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• 제31권1호
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• pp.216-219
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• 2010

• 약학회지
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• 제50권1호
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• pp.21-25
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• 2006

Reiterated normal-phase column chromatography lead to the isolation and purification of six known compounds but for the first time from the whole plant of Sasa borealis (Hack.) Makino (Gramineae): tricin 4'-O-(erythro-${\beta}$-guaia-cylglyceryl) ether (1), tricin 4'-O-(threo-${\beta}$-guaiacylglyceryl) ether (2), tricin 4'-O-[erythro-${\beta}$-guaiacyl-(9'-O-acetyl)-glyceryl] ether (3), tricin 4'-O-[threo-${\beta}$-guaiacyl-(9'-O-acetyl)-glyceryl] ether (4), (-)-pinoresinol (5), and vanillin (6). The structures of the compounds (1-6) were established based on interpretation of high resolution NMR (COSY, HSQC, HMBC, and NOESY) spectral data. In particular, compounds 1 and 3 were diastereomers of compounds 2 and 4, respectively. These two sets of diastereomers were able to be simultaneously identified and quantified by a gradient reversed-phase HPLC method with UV photodiode array, This sensitive HPLC method is noteworthy as a simultaneous separation and identification method to test the extract of the family Gramineae which contains these compounds.

• 대한화학회지
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• 제55권6호
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• pp.940-951
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• 2011

Reaction of 1-methylpyrimidine-(1H,3H,5H)-2,4,6-trione (1-MBA 1) as an unsymmetrical barbituric acid with cyanogen bromide and various aldehydes in the presence of triethylamine and/or pyridine afforded diastereomeric mixtures of new class of heterocyclic stable 5-aryl-1,1'-dimethyl- and 5-aryl-3,1'-dimethyl-1H,1'H-spiro[furo[2,3-d]pyrimidine-6,5'-pyrimidine]2,2',4,4',6'(3H,3'H,5H)-pentaones which are dimeric forms of 1-methyl barbiturate at the range of $0^{\circ}C$ to room temperature. In the reaction of some aldehydes with 1-MBA and BrCN were afforded a mixture of diastereomers. Another two aldehydes such as 4-cyano- and 2-hydroxybenzaldehydes gave exclusively two diastereomers in which binded to the salt of triethylammonium hydrobromide by intermolecular H-bond in ratio of 1:1. 4-Hydroxybenzaldehyde and 2-pyridinecarbaldehyde gave exclusively one diastereomer under the same condition. Aldehydes possessing strong electron-donor were produced exclusively two geometric isomers of Knoevenagel adduct (E- and Z-isomers). The structures of compounds were deduced by $^1H$ NMR, $^{13}C$ NMR and FT-IR spectroscopy. Mechanism of the formation is discussed.

• 약학회지
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• 제41권6호
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• pp.698-703
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• 1997

Recently, l-deprenyl (selegiline), a relative new antiparkinson`s drug, has been marketed in Korea. As its metabolites, l-methamphetamine and l-amphetamine, are the enantiomers of illicit drugs,d-methamphetamine and d-amphetamine, a method for analysis of enantiomers of methamphetamine and amphetamine in rat urine was investigated. The optical isomers of methamphetamine and amphetamine were analyzed with the chiral derivatizing reagent (S)-(-)-N-(trifluoroacetyl)-prolyl chloride (l-TFP), which was used to form the diastereomers of methamphetamine and amphetamine. And all diastereomers (l-TFP -l-AM, lTFP-d-AM, l-TFP-l-MA & l-TFP-d-MA) were well resolved by capillary gas chromatography. After administration of 10mg/kg l-deprenyl to rat, l-methamphetamine and l-amphetamine were detected without autoracemization to the d form in all urine samples collected during 24hrs, and the ratios of l-amphetamine/l-methamphetamine were 1.1~3.3. l-Amphetamine was detected in only 3 out of 8 urine samples collected during 24~48hrs where as no l-methamphetamine was detected in all cases.

• 생약학회지
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• 제51권4호
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• pp.297-301
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• 2020

Silymarin (SM) and silybin diastereomers (SD) in milk thistle (Silybum marianum) were determined using high-performance liquid chromatography and quantified using a reverse-phase column in a gradient elution system. UV detection was performed at 288 nm. The content of SM and SD in milk thistle was 3.236 and 0.553 mg/g DW, respectively. Determining the presence and quantifying the content of SM and SD in milk thistle are vital for the pharmaceutical industry to identify optimal sources for developing health supplements or therapeutics.

• Bulletin of the Korean Chemical Society
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• 제20권11호
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• pp.1309-1312
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• 1999

Two chiral stationary phases (CSPs) derived from two diastereomers consisting of (R)- or(S)-α-naphthylethylamine and (S)-naproxen were found to show different chromatographic behaviors in resolving N-(3,5-dinitrobenzoyl)-α-arylalkylamines and N-(3,5-dinitrobenzoyl)-α- or β-amino amides and esters. From the different chromatographic resolution behaviors on the two CSPs, the chiral recognition is proposed to be controlled mainly by the (R)- or (S)-α-naphthylethylamine part of the CSP. In contrast, the (S)-naproxen part of the two CSPs is proposed to exert some subordinate effects on the chiral recognition.

• 대한약학회:학술대회논문집
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• 대한약학회 2003년도 Proceedings of the Convention of the Pharmaceutical Society of Korea Vol.1
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• pp.275.2-276
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• 2003

Several ${\beta}$-agonists were investigated for the possible separation of the enantiomers by reversed-phase high-performance liquid chromatography after derivatization with a new chiral derivatization agent, GATC. The derivatization proceeded quantitatively within 1 h at room temperature. The corresponding diastereomers were well resolved an ODS column with acetonitrile-acetate buffers a mobile phase and monitored at UV 254nm. (omitted)

• Archives of Pharmacal Research
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• 제23권1호
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• pp.26-30
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• 2000

The enantiomers of the bronchodilator terbutaline were separated by reversed-phase high performance liquid chromatograhy after derivatization with 2,3,4,6-tetra-O-acetyl-\beta-D-glucopyranosyl isothiocyanate(GITC) reagent. The derivatization proceeded quantitatively within 1 h at room temperature. The corresponding diastereomeric thiourea derivatives were well resolved on an ODS column with acetonitrile-acetate buffer as a mobile phase. Elution orders of the diastereomers were confirmed by derivatization of R-(-)-terbutaline and S-(+)-terbutaline which were collected by semi-preparative chiral HPLC using Sumichiral OA-4700 column. The native fluorescence of terbutaline was quenched by derivatization with GITC. The detection limit was 25ng when monitored at UV 278 nm.