• Journal of the Society of Cosmetic Scientists of Korea
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• v.35 no.2
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• pp.143-149
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• 2009

Several hydroxycinnamic acid derivatives, p-coumaric acid, ferulic acid, N,N'-dicoumaroylputrescine (DCP), N-p-coumaroyl-N'-feruloyl-putrescine (CFP), and N,N'-diferuloylputrescine (DFP) were isolated and purified from corn bran. To develop the skin whitening agent, we investigated the effects of hydroxycinnamic acid derivatives from corn bran, on melanogenesis. CFP and DFP inhibited melanin synthesis in a dose dependent manner up to 44.7 ${\pm}$ 6.0 %, and 58.5 ${\pm}$ 3.1 % at a concentration of 50 ${\mu}g/mL$, respectively. The intracellular tyrosinase activity decreased about 42.5 ${\pm}$ 14.6 %, and 9.0 ${\pm}$ 4.4 % at a concentration of 50 ${\mu}g/mL$ of CFP and DFP, respectively. Our results suggest that inhibitory effects of hydroxycinnamic acid derivatives on melanogenesis are due to the inhibition of the intracellular tyrosinase activity. These results indicate that these hydroxycinnamic acid derivatives from corn bran may be potential natural skin whitening agents.

• Journal of Pharmaceutical Investigation
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• v.23 no.3
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• pp.155-163
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• 1993

Inclusion complexation of 1,7,21,27-tetraaza[7.1.7.1]paracyclophane (CPM 55) with 2,7-dihydroxynaphthalene (2,7-DHN) or 1,3-dihydroxynaphthalene (1,3-DHN) in pD 1.17 $DCl-D_2O$ solution was investigated by $^1H$ nuclear magnetic resonance spectroscopy (NMR) using 4,4'-dimethylaminodiphenylmethane (ACM 11) as an acyclic analog of CPM 55. In CPM 55-naphthalene derivative complex, alkyl protons located in the cavity of CPM 55 were shown to be subjected to anisotropic shielding and protons of naphthalene moiety shifted remarkably to upfield. However, in ACM 11-naphthalene derivative systems, chemical shifts for protons of both DHN compounds were not significant. The remarkable chemical shift changes suggested that the naphthalene moiety of 2,7-DHN or 1,3-DHN was included in the hydrophobic cavity of CPM 55 in aqueous solution. From the continuous variation plots of induced chemical shifts of 2,7-DHN, it was found that 2,7-DHN was included in the cavity of CPM 55 at 1:1 molar stoichiometry. Both computer simulation of a inclusion complex and strong upfield chemical shift changes of 2,7-DHN protons supported the conformation of pseudoaxial inclusion as the presumed geometry of the host-guest complex.

• Journal of Applied Biological Chemistry
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• v.51 no.2
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• pp.57-60
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• 2008

Eight compounds, including 2 flavones, luteolin (1) and apigenin (2), 2 flavonols, kaempferol (3) and quercetin (4), and 4 flavonoid glucosides, luteolin-7-O-${\beta}$-D-glucoside (5), apigetrin (6), astragalin (7), and isoquercitrin (8), isolated from the whole herb of Sonchus oleraceus L. were analyzed on the basis of chemical and spectroscopic evidence. This was the first time to report compounds 3, 4, 6, 7 and 8 from the Sonchus oleraceus L. The antioxidant activities of the isolated flavonoids and their glucoside derivatives were evaluated by DPPH free radical-scavenging assay, showing that compounds 1, 3, 4 and 8 exhibited stronger antioxidant activities compared with ${\alpha}$, tocopherol and curcumin. Flavonoids containing more hydroxyl groups exhibited better antioxidant activities. The antioxidant activity of flavonols was superior to their corresponding flavones, and that of aglycone are more potent than their glucoside derivatives.

• Biomolecules & Therapeutics
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• v.7 no.2
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• pp.164-169
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• 1999

The synthesis and antimicrobial activity of N-substituted glycol derivatives of Norfloxacin were described. Norfloxacin was treated with chloroacetyl chloride to yield chloroacetyl norfloxacin (1). This compounds was reacted with alkyldiamines to afford bivalent ligand quinolone carboxylic acids (2-6), which was added to pivaloyloxymethyl chloride to give bivalent ligand pivaloyloxymethyl quinolone carboxylates (7-11). Chloroacetyl norfloxacin (1) treated with alkylamines to obtain monovalent ligand quinolone carboxylic acids (12-15), which was reacted with pivaloyloxymethyl chloride to get monovalent ligand pivaloyloxymethyl quinolone carboxylates (16-19). Free carboxylic quinolones (2-6, 12-15) showed little stronger activities to their pivaloyloxymethyl esters (7-11, 16-19). In monovalent ligand quinolone analogues, longer a1kyl chain com-pounds showed stronger activities than shorter one.

• Proceedings of the Korean Society of Toxicology Conference
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• 2001.10a
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• pp.161-161
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• 2001

Resveratrol (trans-3, 4', 5-trihydroxystilbene), which is a polyphenolic compound found in a variety of plants such as grapes and wine, has been reported to have a variety of anti-inflammatory, anti-platelet, and anti-carcinogenic effects. Recently resveratrol was reported to serve as an estrogen agonist in MCF-7 cells Based on its structural similarity to diethylstilbestrol, a synthetic estrogen, we examined whether resveratrol and its derivatives might be estrogenic using stable MCF-7-ERE cells. (omitted)

• Archives of Pharmacal Research
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• v.28 no.5
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• pp.509-517
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• 2005

A series of structurally diverse amide derivatives of [6-(3,5-dimethyl-4- chloro-pyrazole-1-yl)-3(2H)-pyridazinone-2-yl]acetic acid were prepared and tested for their in vivo analgesic and anti-inflammatory activity by using p-benzoquinone-induced writhing test and carrageenan induced hind paw edema model, respectively. The analgesic and anti-inflammatory activity of the compounds, 7c, 7d and 7k were found to be equipotent to aspirin (as an analygesic) and indometacin (as an anti-inflammatory drug), respectively. The other amide derivatives generally resulted in lower activity on comparision with reference compounds.

• Bulletin of the Korean Chemical Society
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• v.34 no.11
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• pp.3317-3321
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• 2013

A series of new 3-alkylamino-6-allylthio-pyridazine derivatives was synthesized through allythiolation and amino-de-halogenation and were expected to have anti-proliferative activity. 6-Allylthio-3-chloropyridazine was prepared from the reaction of 3,6-dichloropyridazine with allylmercaptan and sodium hydroxide. The alkylamines such as methylamine and the dialkylamines such as dimethylamine were introduced into the 3-position of the pyridazine ring. These new compounds showed anti-proliferative activities against MCF-7 human breast cancer cells in CCK-8 assays. These compounds are thus promising candidates for chemotherapy of breast cancer. Two compounds, 14 and 15, showed higher potencies for inhibiting growth of breast cancer cells than did 5FU. This suggests the potential anti-proliferative activity of these compounds.

• YAKHAK HOEJI
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• v.35 no.6
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• pp.515-521
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• 1991

A number of 1-ethyl-6-fluoro-1,4-dihydro-4-oxo-7-(4-substitutedcarbamyl-1-piperazinyl) quinoline [or 1,8-naphthyridine]-3-carboxylic acid and their pivaloyloxymethyl esters were prepared. The compounds synthesized were evaluated for antibacterial activity in vitro against Escherichia coli, Bacillus subtilis, Proteus vulgaris, Klebsiella pneumoniae, Staphylococcus aureus and Pseudomonas aeruginosa. Among those 1-ethyl-6-fluoro-1,4-dihydro-4-oxo-7-(4-methylcarbamyl-1-piperazinyl) quinoline-3-carboxylic acid [1] and 1-ethyl-6-fluoro-1,4-dihydro-4-oxo-7-(4-methylcarbamyl-1-piperazinyl)1,8-naphthyridine-3-carboxylic acid [6] showed the most potent in vitro antibacterial activity.

• Bulletin of the Korean Chemical Society
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• v.11 no.1
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• pp.7-10
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• 1990

The interaction of tetraphenylphthalic anhydride with o-chlorotoluene under Friedel-Craft condition gives 2-(4-chloro-3-methyl)benzoyl-3,4,5,6-tetraphenyl benzoic acid(1), which on reaction with hydrazine derivatives gave phthalazinones (2a-d). The behaviour of (2a) towards carbon electrophiles and carbon nucleophiles has been investigated. The chlorophthalazinones (4a) also has been synthesized from the action of $PCl_5/POCl_3$ on (2a). The behaviour of (4a) towards nitrogen, and oxygen nucleophiles also have been described.

• Bulletin of the Korean Chemical Society
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• v.12 no.6
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• pp.633-635
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• 1991

3,4,5,6-Tetrahydro-7-hydroxy-2-(1,3-dithian-2-yl)- 9-alkyl-2,6-methano-2H-1-benzoxocin derivatives are readily prepared by boron trifluoride etherate-catalyzed formation of 5-alkylresorcinols with 1-thioxolanyl-2-cyclohexenol. The yieldis the highest with 5-(1,1-dimethylheptyl)resorcinol. The one with 5-pentylresorcinol is higher than with 5-methylresordnol and resorcinol apparently because of steric effects. The yields of the product increase; 3a(7%), 3b(22%), 3c(38%) and 3d(50%).