• Bulletin of the Korean Chemical Society
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• v.33 no.4
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• pp.1253-1258
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• 2012

Two phenolic allopyranosides and two phenolic amide allopyranosides, along with eight known phenolic compounds, including cimicifugic acids, shomaside B, fukiic acid, isoferulic acid, and piscidic acid, were isolated from the n-butanolic extract of rhizomes of Cimicifuga heracleifolia. On-line spectroscopic data for UV, NMR, and MS from a combination of LC-NMR and LC-MS techniques directly and rapidly provided sufficient structural information to identify and confirm all the structures of major phenolic compounds in the extract, in addition to their HPLC profiles. This combined analytic information was then used as a dereplication tool for structure-guided screening in order to isolate unknown phenolic compounds in the extract. Successive fractionation and purification using semi-preparative HPLC acquired four unknown allopyranosides, and their structures were identified as cis-ferulic acid 4-O-${\beta}$-D-allopyranoside, trans-ferulic acid 4-O-${\beta}$-D-allopyranoside, trans-feruloyltyramine 4-O-${\beta}$-D-allopyranoside, and trans-feruloyl-(3-O-methyl)dopamine 4-O-${\beta}$-D-allopyranoside, based on a subsequent spectroscopic interpretation.

• Journal of the Korean Chemical Society
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• v.17 no.4
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• pp.275-285
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• 1973

The addition of one mole of aluminum chloride to three moles of sodium borohydride in tetrahydrofuran gives a turbid solution with enormously more powerful reducing properties than those of sodium borohydride itself. The reducing properties of this reagent were tested with 49 organic compounds which have representative functional groups. Alcohols liberated hydrogen immediately but showed no sign of hydrogenolysis of alkoxy group. Aldehydes and ketones were reduced rapidly within one hr. Acyl derivatives were reduced moderately, however, carboxylic acids were reduced much more slowly. Esters, lactones and epoxides were reduced readily than sodium borohydride or borane. Tertiary amide was reduced slowly, however, primary amide consumed one hydride for hydrogen evolution but reduction was sluggish. Aromatic nitrile was reduced much more readily than aliphatic nitrile. Nitro compounds were inert to this reagent but azo and azoxy groups were slowly attacked. Oxime was reduced slowly but isocyanate was only partially reduced. Disulfide and sulfoxide were attacked slowly but sulfide and sulfone were inert. Olefin was hydroborated rapidly.

• Food Science of Animal Resources
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• v.21 no.3
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• pp.256-264
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• 2001

Pyrolysis/GC-mass spectrometry(Hewlet-Packard 5890GC/mass selective detector, 5971 BMSD), interfaced to a CDS Pyroprobe 1500 was optimized for rapid analysis of flavour compounds in Cheddar cheese. Twenty flavour compounds, including aldehydes(4), ketones(4), fatty acids(10), alcohol(1), and hydrocarbon(1), were identified from Cheddar cheeses. In total, Twenty-three flavour compounds aldehydes(2), ketones(8), alcohols(3), fatty acids(7), lactone(1), benzene derivative(1) and amide(1) were identified from two samples of accelerated-ripened Cheddar cheese treated with the proteolytic enzymes of Lactobacillus casei LGY. In total, Twenty-one flavour compounds; aldehydes(2), ketones(5), alcohols(2), fatty acids(11), and lactone(1) were identified from enzyme-modified cheese(EMC) treated with the combination of the proteolytic enzymes of Lactobacillus casei LGY and commercial endopeptidase or lipase. However, All the flavour compounds identified by pyrolysis/GC/MS in samples of ARC and EMC were not determined whether they are recognized as typical Cheddar flavour or not. More studies were requested on the development of methods for a rapid and convienent analysis of dairy fermented products using pyrolysis/GC-mass spectrometry.

• YAKHAK HOEJI
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• v.46 no.3
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• pp.149-154
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• 2002

Six novel 4-aminoantipyrine derivatives as potential nonsteroidal antiinflammatory and analgesic compounds were prepared and their antiinflammatory-analgesic activity were compared with antiprine. Succinyl chloride and Ac $_2$O were reacted with glycine, respectively, to give glycine compounds (3-4, 9-10), which were treated with hydroxysuccinimide and dicyclohexyl carbodiimide to yield active esters (5-6, 11-12), and then reacted with 4-aminoantipyrine to prepare 4-aminoantipyrine derivatives (7-8, 13-14). 4-Aminoantipyrine reacted with succinyl chloride and Ac $_2$O, respectively, to give succinyl bis aminoantipyrine (15) and acetyl aminoantipyrine (16). Compounds (7), (8) and (13) gave comparable antiinflammatory activity to antipyrine.

• Archives of Pharmacal Research
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• v.19 no.2
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• pp.95-99
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• 1996

Four N-adamantyl n-alkanamides were prepared by amide condensation reaction between amantadine and n-alkanoic acid. Their enhancing activity on the penetration of ibuprofen through rabbit skin from petrolatum ointment was evaluated in in-vivo experiment. The experiments showed that the compounds have a strong transdermal penetration-enhancing activity, and their activities were comparable with that of Azone. The measurements of the fluorescence polarization of DP[-i-labelled DPPC liposomes showed that these compounds considerablly decreased the phase transition temperature of the liposomes. The mechanism of the transdermal penetration-enhancing activity of the compounds was ascribed to the reduction of the resistance to drug flux of the stratum corneum lipid layers due to the loose packing of the layers when the bulk head group of the enhancers inserts into the layers.

• Natural Product Sciences
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• v.21 no.3
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• pp.196-204
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• 2015

Nineteen compounds, including one organic acid (1), one anthraquinone (2), one amide (3), and sixteen triterpenoid saponins (4 - 19) were isolated from the leaves of Acanthopanax henryi (Oliv.) Harms (Araliaceae). Their structures were determined on the basis of physicochemical properties and spectral analyses (HR-MS and NMR). Among them, compounds 2, 3, 7, 12 and 19 were new within Araliaceae. Compounds 4, 5, 9 - 11, 13, 14, 16 and 18 were reported for the first time from the Acanthopanax genus. Except for compounds 4 and 9, other compounds were isolated from A. henryi (Oliv.) Harms for the first time. The rare anthraquinone, compound 2, significantly decreased the production of NO and the levels of other inflammatory factors, such as TNF-α and IL-6, in lipopolysaccharide (LPS)-stimulated macrophages in a dose-dependent manner. This is the first time to report anti-inflammatory effect of this compound.

• YAKHAK HOEJI
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• v.30 no.4
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• pp.163-168
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• 1986

Thirteen compounds were synthesized by condensing the N-heterocyclic amines (piperidine, pyrrolidine, morpholine) and secondary aliphatic amines (dimethylamine, diethylamine) with 3,4-methylenedioxyphenylalkenoic acid chlorides for developing CNS depressants. Among them, N, N-diethyl-3,4-methylenedioxycinnamamide (IX) and N, N-dimethyl-5-(3,4-methylenedioxyphenyl)-2, 4-pentadienoic acid amicle (XII) exhibited strong activity in antagonism against pentylenetetrazole-induced convulsion, strychnine-induced convulsion and maximal electroshock seizure. N, N-Dimethyl-3, 4-methylenedioxycinnamide (VIII) showed more potent activity in antagonism against strychnine-induced convulsion and maximal electroshock seizure and in the prolongation of hexobarbital sleeping time.

• Archives of Pharmacal Research
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• v.25 no.3
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• pp.250-257
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• 2002

A series of benzimidazole derivatives carrying different heterocycles such as 1,2,3-thiadiazole, 1,3,4-thiadiazole, thiazolidine, 2,3-dihydro-thiazole, 1,3,4-oxadiazole, semicarbazone and substituted thiosemi-carbazones were synthesized. Also a series of 1-methylbenzimidazole carrying hydroxy ethyl-amide, substituted sulfonyl hydrazide and benzoyl hydrazide from aminobenzoyl group at position 2 of 1-methylbenzimidazole were synthesized. The antimicrobial evaluation of some of the new compounds was carried out.

• YAKHAK HOEJI
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• v.27 no.4
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• pp.283-287
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• 1983

In order to search more active and less toxic central nervous depressants, piperic acid amides were synthesized by condensation of piperonal with crotonic acid amides. The bioassay results revealed that, among the compounds synthesized, the piperonic acid methylamide and ethylamide exhibited potent protective activity against strychnine-induced convulsion.

• Proceedings of the PSK Conference
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• 2003.04a
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• pp.232.1-232.1
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• 2003

Bradykinin is an autocoid related to acute and chronic pain and inflammation. The non-peptide bradykinin antagonists are of interest as novel anti-inflammatory therapeutics and some active compounds such as FR 173657, LF 16-0687, and bradyzide were reported very recently. In our search for the new bradykinin antagonists, we designed to synthesize the analogues of FR173657 with two to three amide bonds and lipophilic ring system in each molecule. (omitted)