• Bulletin of the Korean Chemical Society
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• v.32 no.1
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• pp.153-156
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• 2011

A concise synthesis of (${\pm}$)-rhinacanthin A is achieved in two steps by epoxidation of dehydro-$\alpha$-lapachone, followed by chemo- and regioselective reduction. Dehydro-$\alpha$-lapachone was also synthesized in two steps starting from 4-methoxy-1-naphthol by ethylenediamine diaetate (EDDA)-catalyzed benzopyran formation and a CAN-mediated oxidation reaction. $\beta$-Lapachone was synthesized in three steps from 4-methoxy-1-naphthol by benzopyran formation, catalytic hydrogenation, and Jones oxidation. As additional reactions, synthesis of pyranonaphthoquinone derivatives with the pyranokunthone B skeleton has been achieved in a single step from readily available 2-hydroxy-6-methoxy-1,4-naphthoquinone and 2-hydroxy-7-methoxy-1,4-naphthoquinone.

• Bulletin of the Korean Chemical Society
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• v.23 no.11
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• pp.1658-1660
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• 2002

• Bulletin of the Korean Chemical Society
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• v.33 no.6
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• pp.2087-2090
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• 2012

• Bulletin of the Korean Chemical Society
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• v.13 no.4
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• pp.351-352
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• 1992

• Textile Coloration and Finishing
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• v.22 no.3
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• pp.181-186
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• 2010

A thermoresponsive poly(NIPAM-co-dye) labeled with benzopyran-based D-$\pi$-A type dye was prepared by typical radical copolymerization. It can be also constructed a acid/base-induced molecular switch by modulation of intramolecular charge transfer with protonation/deprotonation. The lower critical solution temperature behavior was investigated by means of UV-vis spectroscopy which allows the measurement of the phase transition from $25^{\circ}C$ to $45^{\circ}C$ in aqueous DMSO solution. The morphology of the internal microstructure of the poly(NIPAM-co-dye) hydrogel was observed by scanning electron microscopy. The reversible switch could be obtained by thermal and acid/base stimuli.

• Archives of Pharmacal Research
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• v.28 no.10
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• pp.1131-1134
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• 2005

Two new benzopyrans 6-[1'-oxo-3'(R)-hydroxy-butyl]-5,7 -dimethoxy-2,2-dimethyl-2H-1-ben-zopyran (1) and 6-[1'-oxo-3'(R)-methoxy-butyl]-5,7 -dimethoxy-2,2-dimethyl-2H-1-benzopyran (2) were isolated from the leaves of Mallotus apelta Muell.-Arg., (Euphorbiaceae). Their chemical structures were elucidated by spectroscopic analyses, especially by 1D-, 2D-NMR and MS spectra. Compound 1 was found to have strong cytotoxic effect against two human cancer cell lines as human hepatocellular carcinoma (Hep-2, $IC_{50}\;:\;0.49\;{\mu}g/mL$) and rhabdosarcoma (RD, $IC_{50}\;:\;0.54\;{\mu}g/mL$), while compound 2 showed moderate activity against Hep-2 cell line ($IC_{50}\;:\;4.22\;{\mu}g/mL$) by in vitro assay.

• Korean Journal of Crystallography
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• v.8 no.2
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• pp.138-143
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• 1997

The crystal structure of isoimperatorin, f-[(3-methyl-2-butenyl)oxy]-7H-furo[3,2-g][1] benzopyran-7-one, has been determined from single crystal x-ray diffraction study; C16H14O4, Monoclinic, P21/c, a=8.865(1) Å, b=9.331(1) Å, c=16.156(1) Å, β=98.12(1)', V=1322.9(2) Å3, T=293(2)K, z=4, Cu Kα(λ=1.5418 Å). The structure was solved by direct method and refined by full-matrix least squares to a final R=5.72% for 1922 unique observed Fo>4o(F0) reflections and 182 parameters.

• Journal of Applied Biological Chemistry
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• v.64 no.3
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• pp.317-322
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• 2021

Among the different cardiovascular disorders (CVDs), the activation of platelets is a necessary step. Based on this knowledge, therapeutic treatments for CVDs that target the disruption of platelet activation are proving to be worthwhile. One such substance, a bioactive 6,7-dihydroxy derived from coumarin, is 6,7-Dihydroxy-2H-1-benzopyran-2-one (esculetin). This compound has demonstrated several pharmacological effects on CVDS as well as various other disorders including diabetes, obesity, and renal failure. In various reports, esculetin and its effect has been explored in experimental mouse models, human platelet activation, esculetin-inhibited collagen, and washed human platelets exhibiting aggregation via arachidonic acid. Yet, esculetin affected aggregation with agonists like U46619 or thrombin in no way. This study investigated esculetin and how it affected human platelet aggregation activated through U46619. Ultimately, we confirmed that esculetin had an effect on the aggregation of human platelets when induced from U46619 and clarified the mechanism. Esculetin interacts with the downregulation of both phosphoinositide 3-kinase/Akt and mitogen-activated protein kinases, important phosphoproteins that are involved in activating platelets and their signaling process. The effects of esculetin reduced TXA₂ production, phospholipase A₂ activation, and platelet secretion of intracellular granules (ATP/serotonin), ultimately causing inhibition of overall platelet aggregation. These results clearly define the effect of esculetin in inhibiting platelet activity and thrombus formation in humans.

• Proceedings of the PSK Conference
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• 2002.10a
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• pp.281.1-281.1
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• 2002

Psoralen(7H-Furo［3.2-g］ ［1］benzopyran-7-one) and angelicin(2-Oxo-[2H]- furo[2.3-h]-1-benzopyran) are angular furocoumarin with diverse photobiological effects. They are major components of Psoralea corylifolia L.(破古紙). Psoralea corylifolia L. is used for a tonic and nursing one's energy. It can be also used for loss of virility. vitiligo. a skin disease, etc.. But a well known and often appreciated side effects f psoralens is the hyperpigmentation caused by this treatment. A women who used the herbal drug-mixed-medicine named'sobaeksu' to treat her vitiligo made a complaint against the orinetal medical doctor. She complained that her skin got burned to 2nd degree by the liquid. 'sobaeksu' through a medical celtficate. So we analyzed the components of that liquid with gas chromatography and gas chromatography/mass spectometry. It has 57.3% ethyl alcohol and two kinds of psoralens. Psoralens were psoralen and angelicin and each one of their contained quantity was 0.128mg/ml and 0.123mg/ml.

• Korean Journal of Weed Science
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• v.30 no.3
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• pp.183-190
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• 2010

The objective of this study was to isolate a herbicidally active compound from curly dock (Rumex crispus), a native weed in Korea and to identify its' chemistry. The $GR_{50}$ value of methanol extracts which is determined by a seed bioassay using rapeseed (Brassica napus) seedlings was $935\;{\mu}g\;g^{-1}$. Activity-directed isolation of ethylacetate extract led to the isolation of ECDA fraction with $GR_{50}$ value $53\;{\mu}g\;g^{-1}$. Based on data of GC-MS, $^1H$-NMR and $^{13}C$-NMR, the chemical structure of ECDA was determined as 2H-furo[2,3-H]-[1]-benzopyran-2-one which is known as angelicin. The $GR_{50}$ values of angelicin to barnyardgrass (Echinochloa crus-galli), southern crabgrass (Digitaria ciliaris), and indian jointvetch (Aeschynomene indica) were 426, 66 and $216\;{\mu}g\;g^{-1}$, respectively. Our results suggest that angelicin could be used as a lead compound for the development of new herbicides.