• Journal of the Korea Convergence Society
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• v.13 no.1
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• pp.161-166
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• 2022

HIF-2α is a transcription factor activated mainly in hypoxic condition known to play crucial roles in a wide variety of pathophysiological events including cancer, metabolic syndrome, arthritis etc. In this context, a number of N'-aryl isonicotinolyhydrazides, in which known pharmacophores are included, have been selected from commercial chemical library and tested for the inhibitory activities targeting HIF-2α in cultured HTB94 cell. HRE-luciferase and HIF-2α were introduced into the cell by transfection and adenoviri infection, respectively and the reporter gene assay discovered the potency of 2-hydroxy-1-naphthyl structure. Accordingly, the scaffold has been adjusted based on this structure and subjected to anti-HIF-2α activity test, identifying 2 compounds as HIF-2α inhibitors. The activities were confirmed by false positive test. This study has been performed via the convergence of biology and chemistry and the results may be useful for discovering novel inhibitors and HIF-2α biology studies, and contribute to the development of therapeutic agents.

• 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.

• Archives of Pharmacal Research
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• v.22 no.3
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• pp.302-305
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• 1999

An efficient procedure for the preparation of 4-hydroxy-3-{1,2,3,4-tetra-hydro-3-[4-(4-trifluoromethylbenzyloxy)phenyl]-1-naphthyl}thiocoumarin (thioflocoumafen, 1a and 1b) is described. The key step in the synthesis involves the condensation reaction of 3-(4-methoxyphenyl)-1-tetralol (2) with 4-hydroxy-1-thiocoumarin (3).

• Polymer(Korea)
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• v.25 no.6
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• pp.796-802
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• 2001

Novel monomer for polybenzimidazole was prepared and polymerized via aromatic nucleophilic substitution reaction. Thus, N-(4-fluorobenzoyl)-4-methoxy-N'-naphthyl-1,2-phenylenediamine was synthesized from the reaction of 4-methoxy-N-naphthyl-1,2-phenylenediamine and 4-fluorobenzoyl chloride. N-(4-fluorobenzoyl)-4-methoxy-N'-naphthyl-1,2-phenylenediamine was converted to 2-(4-fluorobenzoyl)-5-hydroxy-1-naphthylbenzimidazole by ring closure and demethylation reaction. Polymerization was done in N-cyclohexyl-2-pyrrolidinone (CHP) containing potassium car bonate. The resulting polymer was soluble in N-methyl-2-pyrrolidinone (NMP) and had inherent viscosity of 0.38 dL/g (NMP at $30^{\circ}C$). The glass transition temperature ($T_g$ ) of the polybenzimidazole was $270^{\circ}C$. The thermogravimetric analysis (TGA) thermograms of this polymer showed 5% weight losses at $550^{\circ}C$ in nitrogen and at $540^{\circ}C$ in air.

• Bulletin of the Korean Chemical Society
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• v.33 no.10
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• pp.3361-3367
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• 2012

Two novel Eu(III) complexes with notable properties have been successfully prepared with hydrazone Schiff base ligands, (E)-2-hydroxy-N'-[(2-hydroxynaphthalen-1-yl)methylene]benzohydrazide (3a) and (E)-4-hydroxy-N'-[(2-hydroxynaphthalen-1-yl)methylene]benzohydrazide (3b). DFT, FMO energy and Mulliken charge distribution studies of the ligands allowed us to hypothesize that their HC=N, > C=O and -OH (naphthyl) groups were involved in coordinating with the $Eu^{3+}$ ion. The eight coordination sites of the $Eu^{3+}$ ion were occupied by the three functional groups of the two ligands (3a or 3b) mentioned above and two water molecules. Similar UV, IR and fluorescence spectra indicated the presence of comparable coordination environments for the $Eu^{3+}$ ion in both complexes. Both the ligands and their complexes exhibited moderate DPPH radical scavenging activity. Moreover, it was found that the Eu(III) complexes exhibited fluorescence properties.

• Proceedings of the Korean Vacuum Society Conference
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• 2011.08a
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• pp.321-321
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• 2011

유기발광소자는 낮은 구동전압, 높은 명암비 및 높은 색 재현성 등의 장점을 바탕으로 차세대 디스플레이 및 조명용 광원으로 주목 받고 있다. 또한, 유기발광소자는 발광층을 다층으로 적층하여 적색, 녹색 및 청색을 동시에 발광시켜 단일 소자로 백색 발광소자를 제작할 수 있는 특성을 가지고 있다. 본 연구에서는 백색 유기발광소자를 제작하기 위하여 두 유기물 사이에서 나타나는 엑시플렉스 현상을 이용하였다. 엑시플렉스 현상으로 인한 발광 특성 변화를 관찰하기 위하여 낮은 highest occupied molecular orbital에너지 준위를 가지는 4,4',4''-tris(2-methylphenyl-phenylamino)triphenylamine (m-MTDATA)를 tris(8-hydroxy-quinolinato)aluminum 또는 N,N'-bis(1- naphthyl)-N,N'-diphenyl-1,1'-biphenyl-4,4'-diamine과 혼합하여 발광층을 제작하였다. 엑시플렉스 현상을 관측하기 위해 제작된 유기발광소자의 전기적 및 광학적 특성을 측정한 결과 엑시플렉스 현상으로 인한 발광 특성의 변화가 나타났으며 인가된 전압에 따라 엑시플렉스 현상의 변화를 확인하였다. 엑시플렉스 현상을 이용한 백색 유기발광소자를 제작하기 위하여 4-(dicyanomethylene)-2-methyl-6-(p-dimethyl aminostyryl)-4H-pyran (DCM1)을 9,10-di(2-naphthyl)anthracene층과 m-MTDATA층 사이에 얇게 삽입하여 발광층을 형성하였다. 제작된 백색 유기발광소자의 전기적 및 광학적 특성을 측정한 결과 DCM1이 엑시플렉스 현상을 이용하여 적색 빛을 발광하는 것을 알 수 있었다. 본 연구는 엑시플렉스 현상을 이해하고 응용하는데 많은 도움을 준다.

• Proceedings of the Korea Society of Environmental Toocicology Conference
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• 2003.05a
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• pp.188-188
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• 2003

Examination was made of the urinary metabolite(s) of CKD-712, which is a chiral compound, named S-YS49 derived from higenamine (one component of Aconite spp.) derivatives. First of all, to analyze the metabolite(s) of CKD-712, a simple and sensitive detection method for CKD-712 was developed by using gas chromatography-mass spectrometry GC/MS). Urine was collected from adult male Sprague-Dawley rats 250${\pm}$10g) in metabolic cage for 24hr after oral administration of 100 mg/kg of CKD-712. The recovery of CKD-712 after extraction and concentration with AD-2 resin column was above 90 % from rat urine. The detection limits of CKD-712 in urine was approximately 0.1 ng/mL. It has well been suggested that isoquinoline possessing catechol moiety such as CKD-712 should be subjected to the catechol-O-methyl kransferase activity in vivo. We detected three major peaks of presumed CKD-712 metabolites in the total ion chromatogram obtained from the rat urine sample after oral administration of CKD-712. From these results, it is assumed that the urinary metabolites are mono-methylation in the naphthyl moiety (metabolite I ), methylation at the C-6 or 7 hydroxy group in the isoquinoline moiety and hydroxylation at in the naphthyl moiety (metaboliteII), and methylation at the C-6 or 7 hydroxy group in the isoquinoline moiety (metaboliteIII).

• Bulletin of the Korean Chemical Society
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• v.29 no.1
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• pp.94-98
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• 2008

A fundamental study was developed concerning the novel solvent extraction of the tetravalent metal ions; zirconium(IV), hafnium(IV) and thorium(IV). Their extraction behavior in toluene was investigated with a recently synthesized naphthol-derivative Schiff base, 1-({[4-(4-{[(E)-1-(2-hydroxy-1-naphthyl)methyliden]amino}phenoxy) phenyl]imino}methyl)-2-naphthol (HAPMN). The spectrophotometrical examination of the complex formation between HAPMN and the Zr(IV), Hf(IV) and Th(IV) ions in acetonitrile revealed the formation of stable 1:1 complexes in the solution. After the thorium extraction in toluene, it was found that [Th(OH)3HA] was the respective deriving substance. While, in the case of zirconium and hafnium extraction, the extracted adduct was found to be [M4(OH)8(H2O)16Cl62HA]. The stoichiometric coefficients of these extracted species were determined by the slope analysis method. The extraction reaction followed a cation exchange mechanism.