• Proceedings of the PSK Conference
• /
• 2003.10b
• /
• pp.175.4-176
• /
• 2003

Our long-term research goals involve the SARs study and the synthetic procedure development of wogonin and its analogs. We investigated efficient synthetic pathways of wogonin and its bioisosteres in a large quantity to decipher the structural requirements for anti-inflammatory activities. We plan to serially delete or modify the 5,7-dihydroxyl groups of wogonin to observe the effects of the hydroxyl groups on anti-inflammatory activity. Also we modofied the 8- methoxy group on a ring since it is known to be necessary for biological activity. (omitted)

• Bulletin of the Korean Chemical Society
• /
• v.20 no.1
• /
• pp.42-48
• /
• 1999

We have performed a quantum-chemical investigation on the conformations and electronic properties of a variety of methoxy-substituted poly(p-phenylenevinylenes) (PPVs) to elucidate the effects of alkoxy substitution. Geometrical parameters for the polymers were fully optimized through Austin Model I (AM I) semi-empirical Hartree-Fock (HF) band calculations. Electronic properties of the polymers were obtained by applying the AM I optimized structures to the modified extended Huckel method. To confirm validity of the AM I conformational results, we also carried out ab initio HF calculations with the 6-31G (d) basis set for a variety of methoxy-substituted divinylbenzenes. It is found that the potential energy surfaces of alkoxy-substituted PPVs are quite shallow around the planar conformations, suggesting that the prepared films possess a variety of conformations with different torsion angle in the solid state, depending on the synthetic conditions. When two alkoxy groups are concurrently substituted at the adjacent sites in the phenylene ring, these groups are subject to rotating around the C(sp2)-O bonds by 70-80° to avoid the strong steric repulsion between them. Consequently, the overlap between the π-type p orbital of oxygen and the π molecular orbitals of the polymer decreases. This leads to a wide gap and a high oxidation potential for tetramethoxy-substituted PPV, compared to those of dialkoxy-substituted PPV.

• Korean Journal of Food Science and Technology
• /
• v.34 no.4
• /
• pp.604-609
• /
• 2002

The sensory properties and flavor components of the white bread added with arrowroot juice. The lightness of bread crumb decreased significantly as arrowroot juice was added. While the yellowness increased slightly, redness increased remarkably. The hardness, chewiness and adhesiveness of the white bread added with arrowroot juice increased more than those of the control bread, but they had no statistical significance. While the gumminess increased significantly and springiness decreased significantly, the cohesiveness did not indicate significant differences among the comparison groups. In sensory evaluation, the texture, flavor and sweetness did not indicate significant difference among the comparison groups, while the color and overall acceptability indicated significant difference. The optimum concentration of arrowroot juice in the white bread was 25% based on the sensory evaluation scores. The main flavors components of the white bread added with 25% arrowroot juice were compounds translated by arrowroot juice and the compounds formed by amino-carbonyl reaction. The translated flavors were methoxy phenol, ${\beta}-damascenone$, benzylcyanide, and menthofuran. The compounds formed by amino-carbonyl reaction were alkyl pyrazines, pyrroles and furans.

• Journal of Microbiology and Biotechnology
• /
• v.13 no.4
• /
• pp.632-635
• /
• 2003

Novel poly(3-hydroxyalkanoates), PHAs, having either methoxy or ethoxy groups as the terminal hydrophilic moieties, were biosynthesized by Pseudolnons oleovorans. grown either solely with 11-alkoxyundecanoic acid or 8-alkoxyoctanoic acid, or grown with a mixture of 6-alkoxyhexanoic acid and nonanoic acid. The PHA synthesized from 11-methoxyundecanoic acid consisted of 88 mol% 3-hydroxy-7-methoxyheptanoate and 12 mol% 3-hydroxy-9-methoxynonanoate. However, the PHA produced from 11-ethoxyundecanoic acid consisted of 56 mol% 3-hydroxy-5-ethoxypentanoate and 44 mol% 3-hydroxy-7-ethoxyheptanoate. The high solubility of the PHAs in methanol and ethanol indicated that the alkoxy groups in the side chains resulted in the formation of PHAs with an enhanced hydrophilicity.

• Applied Chemistry for Engineering
• /
• v.5 no.2
• /
• pp.189-198
• /
• 1994

The adsorptive behaviors of carbon monoxide and methanol over $V_2O_5$catalyst were studied by means of thermal desorptlon spectroscopy (TDS) under ultrahigh vacuum conditions. Carbon monoxide adsorbed on oxygen-deficient V sites as well as on V=O groups of the $V_2O_5$ surface. CO adsorbed on the V sites desorbed at 380 K while CO adsorbed on the V=O groups formed carbonate species with surface oxygen of $V_2O_5$ and desorbed as $CO_2$ resulting in the reduction of the surface of she $V_2O_5$catalyst. The amount of CO adsorbed in the form of carbonate species increased by both the pre- and post-adsorbed oxygen. The adsorptive behavior of methanol over the catalyst was studied by thermal desorption experiments of $CH_3OH$, HCHO, CO, and $H_2$ upon methanol adsorption at 298 K. The results showed that methanol was adsorbed dissociatively on the $V_2O_5$catalyst as methoxy and hydroxyl groups at 298K.

• Archives of Pharmacal Research
• /
• v.27 no.9
• /
• pp.937-943
• /
• 2004

Recent investigations have shown that certain flavonoids, especially flavone derivatives, inhibit nitric oxide (NO) production by inducible NO synthase (iNOS) in macrophages, which contrib-ute their anti-inflammatory action. For the purpose of finding the optimized chemical structures of flavonoids that inhibit NO production, various A- and B-ring substituted flavones were syn-thesized and evaluated for their inhibitory activity using lipopolysaccharide-treated RAW 264.7 cells. It was found that the optimal chemical structures were A-ring 5,7-dihydroxyflavones hav-ing the B-ring 2＇,3＇-dihydroxy or 3＇,4＇-dihydroxy or 3＇,4＇-hydroxy/methoxy (methoxy/hydroxy) groups. These structurally optimized compounds were revealed to be down-regulators of iNOS induction, but not direct iNOS inhibitors. Of these derivatives that were evaluated, 2＇,3＇,5,7-tet-rahydroxyflavone and 3＇,4＇,5,7-tetrahydroxyflavone (Iuteolin) showed the strongest inhibition. The $IC_{50}$/ values for these compounds were 19.7 and 17.1 11M, respectively. Therefore, these compounds may have a potential as new anti-inflammatory agents.

• Journal of the Korean Chemical Society
• /
• v.30 no.1
• /
• pp.109-117
• /
• 1986

7,9-Dideoxydaunomycinone (32), a late-stage precursor of the aglycone of antitumor antibiotic daunorubicin(2a) was prepared from 3-methoxybenzoic acid(5). Thus, 3-methoxybenzoic acid was converted to 4-methoxy-3-(phenylsulfonyl)-1(3H)-isobenzofuranone(11), which furnished trimethoxynaphthoate 16 upon ring annelation developed by Hauser and Rhee. The trimethoxynaphthoate 16 upon ring annelation developed by Hauser and Rbee. The trimethoxynaphtboate 16 was then transformed into phenylsulfonylnaphthofuranone 22, which was used to make anthracenoate 24 via Michael type reaction with 7-(ethylenedioxy)-2-octenoate(23). Conversion of anthracenoate 24 to tetracyclic product 28, followed by subsequent deprotection of the methyl groups in ring-B and C furnished 7, 9-Dideoxydaunomycinone(32).

• Archives of Pharmacal Research
• /
• v.27 no.3
• /
• pp.273-277
• /
• 2004

In previous studies for the development of new anticonvulsants, we found that N-Cbz-$\alpha$-amino-N-alkylsuccinimides exhibited significant anticonvulsant activities in the Maximal electroshock seizure (MES) and Pentylenetetrazole induced seizure (PTZ) tests, and also their anticonvulsant activities were dependent on the N-alkyl substituents existent in their structures. Based on these estimations, N-Cbz-$\alpha$-amino-N-hydroxysuccinimide and various N-Cbz-$\alpha$-amino-N-alkoxysuccinimides were prepared in order to develop more active anticonvulsants and to examine the effects of N-hydoxy or N-alkoxy groups on their anticonvulsant activities. The (R)-or (S)-N-Cbz-$\alpha$-amino-N-hydroxysuccinimide and N-Cbz-$\alpha$-amino-N-alkoxysuccinimides were prepared from the corresponding (R)-or (S)-N-Cbz-aspartic acid through the known synthetic procedures. Their anticonvulsant activities in the MES and PTZ test were evaluated. All of these compounds except 3a showed significant anticonvulsant activities against the PTZ test, but these compounds were not active in the MES test. The most active compound in the PTZ test was (R)-N-Cbz-$\alpha$-amino-N-benzyloxysuccinimide (ED$_{50}$=62.5 mg/kg). In addition, the anti-convulsant activities of these compounds were dependent on their N-substited groups. The order of anticonvulsant activity against the PTZ test, as judged from the ED50 values for (R) series was N-benzyloxy > N-hydroxy > N-isopropoxy > N-methoxy > N-ethoxy; for the (S) series N-ethoxy > N-benzyloxy > N-methoxy > N-isopropoxy.y.

• Archives of Pharmacal Research
• /
• v.18 no.5
• /
• pp.340-345
• /
• 1995

A nebumetone tablet in development $(Navuton^R)$ was tested for its bioequivalence to the erference tablet $(Uniton^R)$. Seventeen healthy Korean male subjects participated in this study. Each subject received a 1-g dose of nabumetone (2tables each) in an unbalanced, randomized, two-way crossover investigation. Serum concentrations of 6-methoxy-2-na-phthylacetic acid (6-MNA), a major metabolite of nebumetone, were measured over 120 hr interval by a high-performance liquid chromatography. The maximum serum concentration $(C_{max})$ and time to reach the maximum concentration$(T_{max})$ were read directly, but area under the serum concentration time curve from time 0 to 120 hr (AUC) and mean residence time serum curves showed multiple peaks of 6-MNA in most subjects, and the $C_{max}$ and $T_{max}$ were read from the highest serum peaks. calculated bioavailability parameters for test and reference tablets were 148.6 : 1377.9 $\mug \cdot hr/ml$ for AUC; 25.2:23.1 $\mu/ml$ for $C_{max}$; 11.8:16.4 hr for $T_{max}$, and 42.6 : 43.8 hr for MRT, respectively. The paired t-test revealed no significant differences in all the parameters between the two tablets. Analysis ofl variance (ANOVA) revealed no significant differences between groups and formulations in all the parameters ($C_{max}$ and $T_{max}$, AUC and MRT) indicating the crossover design of the experiment was properly performed. But significant differences (p<0.05) between subject/groups and periods were found for all the parameters indicating substantial intersubject and interperiodic variations for these parameters.

• YAKHAK HOEJI
• /
• v.55 no.4
• /
• pp.319-323
• /
• 2011

Curcumin, of which a critical characteristic is the capacity of crossing the blood-brain barrier, has been reported to induce the expression of neuroprotective heme oxygenase (HO)-1. The aim of this study is to compare HO-1-inducing capacity and neuroprotective activity of curcumin, its demethoxy (demethoxycurcumin, DMC; bis-demethoxycurcumin, BDMC) and hydrogenated derivatives (tetrahydrocurcumin, THC) in mouse hippocampal HT22 cells. Curcumin attenuated glutamate-induced cell death through HO-1 expression. DMC lacking a methoxy group on one of the aromatic rings possessed slightly lower activity in HO-1 expression and neuroprotection than curcumin. Similarly, BDMC, which lacks two methoxy groups on both of the aromatic rings, showed less activity than curcumin. These findings suggest that the presence of methoxy groups on the aromatic ring is required to enhance neuroprotective HO-1 expression. The reduction of the diarylheptadienone chain of curcumin by hydrogen, as in THC, was accompanied by a complete loss of ability to induce HO-1 expression and neuroprotection, suggesting that the conjugated double bonds of the central seven-carbon chain of curcumin may be essential for its ability to induce neuroprotective HO-1 expression. Our findings may provide useful information for further development of neuroprotective HO-1 inducers.