• Journal of the Korean Chemical Society
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• v.43 no.1
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• pp.92-103
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• 1999

The 8 coumarin derivatives have been synthesized from 8 starting materials(2-hydroxy-benzophenone, 2,2'-dihydroxybenzophenone, 2,4-dihydroxybenzophenone, 2-hydroxy-5-methylbenzophenone, 5-chloro-2-hydroxy-4-methylbenzophenone, 2-hydroxy-4-methoxybenzophenone, 2-hydroxy-4-ethoxybenzophenone, 2-hydroxy-4,4'-dimethoxybenzophenone) with phenylacetic acid and $Ac_2$O/TEA in acetone at reflux temperature. The ratio of o-hydroxybenzophenone, phenylacetic acid, $Ac_2$O and TEA is 1 : 1: 8: 8 in acetone. Our results showed higher products yields of coumarin derivatives than Shama and Ray's method in previous papers. A new intermediate form was proposed to our mechanism of coumarin synthetic method.

• Archives of Pharmacal Research
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• v.18 no.4
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• pp.277-281
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• 1995

An anticoagulant, 4-hydroxy-3-[1, 2, 3, 4-tetrahydro-3-[4-(4-trifluoromethylbenzyloxy)phenyll-1 -naphthyl]coumarin (Flocoumafen) was synthesized in 8 steps starting from phenylacetyl shloride and anisole. The key step in the synthesis involves the reaction of 3-(4-methoxyphenyl)-1-teralol with 4-hydroxycoumarin to give 4-hydroxy-3 [1, 2, 3, 4-tetrahydro-3-[4-emthoxyphenyl]-1-naphthyl]coumarin.

• YAKHAK HOEJI
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• v.13 no.2_3
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• pp.67-70
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• 1969

Gall duct cannulated rats were given daphnetin, umbelliferone, 4-hydroxy-coumarin, dicoumarol, 4,7-dihydroxycoumarin, 4,7-dimethyl-5-hydroxy-coumarin, coumarin-3-carboxylic acid, cinnamic acid, ferulic acid, caffeic acid by duodenal catheter at room temperature and output of bile flow was detected. All of the subjected compounds in this experiment indicated a significant effect on the biliary elimination except cinnamic acid alone. It is suggested that a relationship exists between chemical pattern and biological activity for coumarin derivatives and their precursors, and that the choleretic activity of these compounds requires hydroxylated cinnamic acid structure as the most fundamental chemical pattern.

• Journal of the Korean Chemical Society
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• v.56 no.4
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• pp.459-463
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• 2012

8-Formyl-4-Methyl-7-Hydroxy Coumarin Derivatives were synthesized via Penchem condensation followed by Duffs reaction. Treatment of this with N,N-di substituted cyano acetamides in the presence of piperdine afforded New 8-Formyl-4-Methyl-7-Hydroxy Coumarin Derivatives (7a-o). Their structures were characterized by IR, $^1H$ and $^{13}C$ NMR and Mass spectral and elemental analysis data.

• Journal of the Korean Society of Industry Convergence
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• v.6 no.2
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• pp.109-113
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• 2003

We report herein synthetic results obtained new types of crown ethers containing coumarin group. Crown ethers containing coumarin group 1~3 are hydroxymethyl-15-crown-5-ether linked with 4-hydroxy coumarin-4-acetic acid by esterification reaction. Crown ethers containing coumarin group 1~3 have different cavity in each crown ether rings. The 12-crown-4 ether with coumarin 1 has the smallest cavity size. The 15-crown-5 ether with coumarine 2 has the medium cavity size. The 18-crown-6 ether with coumarin 3 has the largest cavity size. Therefore each crown ether with coumarin group will recognize different ionic radius meta. Because of different hole size in crown ethers, these crown ethers seem to be had different selectivity in luminescent sensors. The crown ethers with coumarine 1~3 synthesized hydroxymethyl-15-crown-5-ether and 4-hydroxy coumarin-4-acetic acid same ratio at one to one. The synthesized crown ethers were characterized respectively by IR, NMR. GC-Mass.

• Natural Product Sciences
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• v.6 no.4
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• pp.179-182
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• 2000

Nine compounds were isolated from the fruit Citrus junos. Their structures were elucidated as 9-hydroxy-4-methoxypsoralen, auraptene, limonin, deacetylnomilin, cirsimaritin, narirutin, naringin, hesperidin and neohesperidin by physico-chemical evidences. 9-Hydroxy-4-methoxypsoralen and auraptene have not been reported from C. junos yet.

• Journal of the Korean Chemical Society
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• v.52 no.3
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• pp.249-256
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• 2008

3-Acetyl/Formyl 4-hydroxy-2H(1)-benzopyran-2-one on treatment with malonitrile and ethyl cyanoacetate yielded 1,1-dicyano-2-[4/-hydroxy-2/H(1)-benzopyran-2/-one-3/-yl] ethene/propene 2a-h and ethyl-2-cyano-3-[4/-hydroxy-2/H (1)-benzopyran-2/-one-3/-yl] propenoate/butenoate 3a-h respectively. The 1,3 dipolar reaction of 2a-h with NaN3 gave the tetrazole derivative 4a-h. 3a-h on cyclization with PPA gave 3-cyano-2H,5H-pyrano [3, 2-c] benzopyran-2,5-diones 5a-h which on 1,3 dipolar reaction with NaN3 to gave 3-(1/H-tetrazol-5/-yl)-2H,5H-pyrano[3, 2-c] benzopyran-2,5-diones 6a-h. The structures of the compounds have been established on the basis of the spectral and analytical data. All the compounds were screened for their antimicrobial activities and have been found to exhibited significant antibacterial activities. Compounds 2h and 4h showed the activity 50g/mL.

• Natural Product Sciences
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• v.21 no.1
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• pp.1-5
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• 2015

Activity-guided separation of the methylene chloride-soluble fraction of the leaves of Zanthoxylum schinifolium, resulted in the isolation of four coumarinoids (1 - 4), two triterpenoids (5, 6) and three fatty acid derivatives (7 - 9) as active principles. Their chemical structures were identified as collinin (1), 8-methoxyanisocoumarin (2), 7-(6'R-hydroxy-3',7'-dimethylocta-2',7'-dienyloxy)-coumarin (3), (E)-4-methly-6-(coumarin-7'-yloxy) hex-4-enal (4), lupeol (5), epi-lupeol (6), phytol (7), hexadec-3-enoic acid (8) and palmitic acid (9), on the basis of spectroscopic (1D, 2D and MS) data analyses and comparing with the data published in the literatures. Compounds 1 and 7 showed potent cytotoxicity against Jurkat T cells with $IC_{50}$ values of 45.58 and $47.51{\mu}M$, respectively. The others showed moderate activity with $IC_{50}$ values ranging around 80.58 to $85.83{\mu}M$, while the positive control, auraptene, possessed an $IC_{50}$ value of $55.36{\mu}M$.

• Archives of Pharmacal Research
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• v.26 no.1
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• pp.15-20
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• 2003

Two quinazolone alkaloids, (+)-febrifugine (1) and isofebrifugine (2), along with three coumarin derivatives, 6-hydroxy coumarin (3), skimmin (5), and $umbelliferone-7-O-{\alpha}-L-rhamnopyranosyl(1{\rightarrow}4)-{\beta}-D-glucopyranoside$ (6), were isolated from the roots of Hydrangea chinensis. Compound 6 is a new compound. In addition, umbelliferone (4), linoleic acid (7), two steroidal glycosides (8, 9), three furfural derivatives (10-12), and butyl-$\beta$-D-fructofuranoside (13) were isolated from the leaves of the same plant. The structures of all isolates were elucidated by spectral methods.

• Archives of Pharmacal Research
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• v.29 no.12
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• pp.1119-1124
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• 2006

The methanol extract from the aerial parts of Dictamnus albus was active in inhibiting monoamine oxidase (MAO) from the mouse brain. Activity-guided fractionation led to the isolation of four known coumarins, 7-(6'R-hydroxy-3', 7'-dimethyl-2'E, 7'-octadienyloxy) coumarin (1), auraptene (2), umbelliferone (3), and xanthotoxin (4), as active compounds along with an inactive alkaloid, skimmianine (5). Compounds 1 and 2 inhibited MAO activity in a concentration-dependent manner with $IC_{50}$ values of 0.7 and $1.7\;{\mu}M$, respectively. Compounds 1 and 2 showed a slight and potently selective inhibitory effect against MAO-B ($IC_{50}\;0.5\;and\;0.6\;{\mu}M,\;respectively$) compared to MAO-A ($IC_{50}\;1.3\;and\;34.6\;{\mu}M,\;respectively$). According to kinetic analyses derived by Lineweaver-Burk reciprocal plots, compounds 1 and 2 exhibited a competitive inhibition to MAO-B.