• Journal of the Korean Chemical Society
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• v.61 no.3
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• pp.97-103
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• 2017

In this study, the functional hydrogel ophthalmic lens containing tungsten oxide nanoparticles, 2,4-dihydroxy benzophenone and 2-hydroxy-4-(methacryloyloxy) benzophenone were manufactured. HEMA (2-hydroxyethyl methacrylate), MMA (methyl methacrylate), AA(acrylic acid), the cross-linker EGDMA (ethylene glycol dimethacrylate), the initiator AIBN (azobisisobutyronitrile) and the functional additives including tungsten oxide nanoparticles, 2,4-dihydroxy benzophenone, and 2-hydroxy-4-(methacryloyloxy) benzophenone were used respectively. The measurements of water content and refractive index of the sample was decreased and increased, respectively. And also, the UV transmittance of produced lens containing 2,4-dihydroxy benzophenone, 2-hydroxy-4-(methacryloyloxy) benzophenone and tungsten oxide nanoparticles was measured. Based on the results of this study, it is judged that the performance improvement increased over time when 2-hydroxy-4-(methacryloyloxy) benzophenone was used as an additive, while the use of tungsten oxide nanoparticles influenced on blue-ray-blocking effect of the hydrophilic lens.

• Analytical Science and Technology
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• v.24 no.3
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• pp.173-182
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• 2011

This research examined prostanozol and its metabolites in urine of women who took the medicine (prostanozol). Prostanozol and its metabolites were successfully separated and detected by using LC/ESI/MS and GC/TOF-MS. Mass spectrum of LC/ESI/MS estimated molecular weight of Prostanozol and its metabolites and that of GC/TOF-MS verified them. For M1, carbon number 17 of Prostanozol substituted to a keto group and it is called 17-keto-Prostanozol. M2 turned out to be hydroxy-17-keto-Prostanozol. It came from substitution of one hydroxyl group of pyrazole nucleus and A-ring of M1. Substitution of one hydroxyl group of B-ring or C-ring became M3, hydroxy-17-keto-Prostanozol. M4 was found to be a hydroxy-17-keto-Prostsnozol transposed from one hydroxyl group to a D-ring. M5 has a hydroxyl group of carbon number 17. One hydroxyl group is substituted from B-ring or C-ring and it is assumed to be hydroxy-17-hydroxy-Prostanozol. M6 was turned out to be dihydroxy-17-keto-Prostanozol transposed from one hydroxyl group to pyrazole nucleus or A-ring and to B-ring or C-ring. Like M6, M7 has a keto group at carbon number 17 and was identified as dihydroxy-17-keto-Prostanozol. M7 has one hydroxyl group at pyrazole nucleus or A-ring and also at D-ring. At last M8 was found to be dihydroxy-17-hydroxy-Prostanozol. Pyrazole nucleus or A-ring has got one hydroxyl group and other rings were substituted to another hydroxyl group. From above, M5, M7 and M8 were verified as new metabolites that were not discovered yet. Prostanozol and all of the 8 metabolites formed glucuronic conjugates as a result of conjugation reaction test in human body. Some of 8 metabolites were excreted without forming conjugates. Particularly M6 and M7 were excreted as sulfate conjugates.

• Archives of Pharmacal Research
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• v.19 no.4
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• pp.286-291
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• 1996

Phenolic compounds are prevalent as toxins or environmental pollutants, but they are also widely used as drugs for various purpose including anticancer agent. A novel biphenolic compound, bis(2-hydroxy-3-tert-butyl-5-methylphenyl)methane (GERI-BPO02-A) was isolated from the fermentation broth of Aspergillus fumigatus F93 previously, and it has revealed cytotoxicity against human solid tumor cells. Its effective doses that cause 50% inhibition of cell growth in vitro against non-small cell lung cancer cell A549, ovarian cancer cell SK-OV-3, skin cancer cell SK-MEL-2 and central nerve system cancer cell XF498 were 8.24, 10.60, 8.83, $9.85\mug/ml$ respectively. GERI-BPO02-A has also revealed cytotoxicity against P-glycoproteinexpressed human colon cancer cell HCT15 and its multidrug-resistant subline HCT15/CL02, and its cytotoxicity was not affected by P-glycoprotein. We have also tested cytotoxicities of structurally related compounds of GERI-BPO02-A such as diphenylmethane, 1,1-bis(3,4dimethylphenyl)ethane, 2,2-diphenylpropane, 2-benzylpyridine, 3-benzylpyridine, $4,4^I-di-tert-butylphenyl$, bibenzyl, $2,2^I-dimethylbibenzyl$, cis-stilbene, trans-stilbene, 3-tert-butyl-4-hydroxy-5-methylphenyisulfide, sulfadiazine and sulfisomidine for studying of structure and activity relationship, and from these data we could suppose that hydroxyl group of GERI-BPO02A conducted important role in its cytotoxicity.

• YAKHAK HOEJI
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• v.39 no.5
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• pp.506-510
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• 1995

The 5-(2'-(N-(1-methyl-3'-carbamylphenyl)-n-propyl))aminoethyl)-8- hydroxy-4-methyl-carbostyril derivatives which have isoelectronic and isosteric structural similarity with dobutamine without having the Catechol-O-Methyltransferase (COMT) vulnerable m-hydroxy group were synthesized via 7 synthetic steps, and their stabilities in phosphate buffer solution(pH=7.4), human blood. 80% human plasma and 20% rat liver homogenate were determined in vitro condition.

• Archives of Pharmacal Research
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• v.8 no.1
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• pp.1-6
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• 1985

The crystal structure or $\gamma$-hydroxy-$\betha$-aminobutyric acid was determined by MULTAN system with X-ray intensity data on a diffractometer and refined by the least-squares method to an R-value 0.034 for 711 reflections. The crystals were orthorhombic, space group $P2_{1}2_{1}2_{1}$, Z = 4, with a = 10.220, b = 8.257 and c = 6.556$\AA$. The molecule takes the zwitterionic form and skeletal conformation is trans-transform. The molecules are held together by intra-and intermolecular NH-O and OH--O hydrogen bonds.

• Bulletin of the Korean Chemical Society
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• v.22 no.9
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• pp.999-1004
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• 2001

(1-Chloro-2,2-dicyanovinyl)benzene or 1,4-bis(1-chloro-2,2-dicyanovinyl)benzene was reacted with 2-amino-phenol to give the model compound, hydroxy enaminonitrile, which was found to undergo thermal cyclization reaction to form the corresponding benzoxazole. This intramolecular cyclization reaction is expected to occur through nucleophilic attack to electropositive enamine carbon by ortho-hydroxy group on the phenyl ring, which is accompanied by the release of neutral malononitrile through rearrangement. From each bifunctional monomer, o-hydroxy substituted polyenaminonitrile was prepared and characterized as a new precursor polymer for well-known aromatic polybenzoxazole. Also the unusual macrocyclic dimer formation from the 1,4-bis(1-chloro-2,2-dicyanovinyl)benzene and 2,2-bis(3-amino-4-hydroxyphenyl)hexafluoropropane polymerization reaction system was discussed. The thermal cyclization reactions and the properties of polymers were investigated using FT-IR and thermal analysis (DSC & TGA).

• Korean Journal of Crystallography
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• v.8 no.2
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• pp.111-118
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• 1997

The structrue of hydroxy-bisbenzoyloxy-allyloxycalix[4]arene (C45H36O6) has been determined by X-ray crystallography. The crystals are monoclinic, space group P21, unit cell constants a=11.045(3), b=33.545(2) c=10.319(4)Å, β=113.86(2)˚, Z=4, V=3496.0(1.8) Å3, DC=1.28 gcm-3. The intensity data were collected on an Enraf-Noninus CAD-4 Diffractometer with a graphite monochromated Mo-Kα radiation. The structure was solved by direct method and refined by full-matrix least-squares calculations to a final R value of 0.076 for 2945 observed reflections. Two independent enantiomeric molecules are crystallized in a 1:1 racemate mixture. They have the flattened cone conformation with the flattening hydroxy1 pheny1 rings. There is an intramolecular hydrogen bond in both molecules.

• Proceedings of the Korean Society of Applied Pharmacology
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• 1994.04a
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• pp.222-222
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• 1994

목적하는 화합물인 2',5'-dihydroxy-3'-무치환 유도체(1)는 uridine을 sodium metaperiodate로 산화하여 dialdehyde를 얻은다음 1,2-dianilinoethane으로 3'-aldehyde만을 선택적으로 보호, 2'-aldehyde를 NaBH$_4$로 환원, alcohol로 하여 deprotection 하므로서 hemiacetal율 얻는다. 이 hemiacetal을 TsSNHHNH$_2$로 처리하여 목적하는(1) 화합물을 얻었으며 2-azido-5-Hydroxy-3'-무치환 유도체(2)는 (1)화합물 합성시 얻은 hemiactal을 출발 물질로 하여 먼저 TBDPSCl로 silyaltion하여 5'-hydroxyl group을 보호하고 TsNHNH$_2$로 3'-위치를 hydrazone으로 한다음 NaB(CNH$_3$로 처리하여 얻은 hydrazide를 NaOAc를 반응시켜 2'-hydroxy-3'-무치환-5'-silyl 유도체를 얻고 또한 2',3'-dihydroxy group을 tosyl화, azido화, 5'-silyl group을 deprotection 하므로서 (2)를 얻었다. 또한 2',3'-dihydroxy-5'-무치환 유도체(4)는 uridine의 2',3'-위치를 먼저 protection, 5'-위치를 benzoyl화 2',3'-deprotection, periodate oxidation하여 얻은 diol을 silyl화 한 다음 5'-위치를 benzoyl화, 2',3'-deprotection, 산화하여 얻은 hemiacetal의 silyl group을 제거한후 primary hydroxyl group만을 선택적으로 silyl화, TsNHNH$_2$, NaB(CN)H$_3$ 및 NaOAc로 처리하므로서 얻은 2'-hydroxy-3'-0-silyl group-5'-무치환 화합물을 tosyl, azido화 한다음 desilylation하여 얻었다. 목적하는(1) 화합물의 diasteromer 인 2',3'-dihydroxy-5'-무치환 유도체(3)는 (4)화합물 합성시 얻은 hemiactal을 key intermediate로 하여 TsNHNH$_2$, NaB(CN)H$_3$ 및 NaOAc로 처리하므로서 얻을수 있었다. 이들 화합물들의 각종 DNA 및 RNA virus에 대한 항 바이러스작용을 검토한 결과 현저한 항 바이러스 작용을 나타내지 않았다.

• Applied Biological Chemistry
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• v.51 no.3
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• pp.171-176
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• 2008

The comparative molecular similarity indices analysis (CoMSIA) models between 3${\beta}$-Hydroxy-12-oleanen-28-oic acid (1-30) analogues as substrate molecule and their inhibitory activities ($pI_{50}$) against protein tyrosine phosphatase (PTP)-1B were derived and discussed quantitatively. Listing in order, the CoMFA>CoMSIA${\geq}$HQSAR>2D-QSAR model, these QSAR models had the better statistical values. The optimized CoMSIA F1 model at grid 3.0${\AA}$ had the best predictability and fitness ($q^2$=0.754 and $r^2$=0.976) by field fit alignment. The order of contribution ratio (%) of CoMSIA fields concerning the inhibitory activities was a H-bond acceptor (48.9%), steric field (25.8%) and hydrophobic field (25.4%), respectively. Therefore, the inhibitory activities of substrate molecules against PTP-1B were dependent upon H-bond acceptor field (A) of $R_4$-group. From the analytical results of CoMSIA contour maps, oleanolic acid derivatives will have better inhibition activities if $R_1$ group has H-bond acceptor disfavor, $R_3$group has steric disfavor and $R_4$ group has steric, hydrophobic, H-bond favor.

• Journal of the Korean Wood Science and Technology
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• v.37 no.1
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• pp.78-86
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• 2009

In this study 2 cadalene homologues - 3,7-dimethoxycadalene and 7-hydroxycadalene-5,8-quinone (keyakinone A)-were further identified from ethanol extracts of Zelkova serrata wood, except 7-hydroxy-3-methoxycadalene. Two biological activities-scavenging activity of hydroxy radical and cell toxicity by MTT assay-were measured with 7-hydroxy-3-methoxycadalene. The scavenging activity of hydroxyl radical of the compound was excellent and increased with its concentration. At 100 ppm hydroxyl radicals were removed completely. However, MTT assay revealed that 7-hydroxy-3-methoxycadalene showed critical toxicity to the cells. When 1 ppm of the compound was treated to the cells, cell viability was reached up to 90%, while it was reduced to 22% after treatment of 9 ppm. In 4 different Ulmaceae species, such as Ulmus davidiana, Ulmus parvifolia, Ulmus macrocarpa, Ulmus macrophylla, 7-hydroxy-3-methoxycadalene was not found at all. Instead, 7-hydroxycadalene (Mw 214), in which methoxyl group is omitted from 7-hydroxy-3-methoxycadalene, was distributed in the heartwood of 4 Ulmaceae species as major cadalene compound.