• 대한약학회:학술대회논문집
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• 대한약학회 2003년도 Proceedings of the Convention of the Pharmaceutical Society of Korea Vol.2-2
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• pp.175.4-176
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• 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
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• 제20권1호
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• pp.42-48
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• 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.

• 한국식품과학회지
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• 제34권4호
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• pp.604-609
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• 2002

칡즙 첨가 식빵의 관능적 특성은 색도, 조직감, 관능평가를 통해 조사하였다. 첨가된 칡즙의 양이 증가할수록, L값은 유의적으로 현저히 감소하였고, b값은 유의적인 증가를 나타냈으며 a값은 유의적으로 현저한 증가를 나타내었다. 경도, 씹힘성과 부착성은 유의성은 없으나 증가한 반면 껌성질은 유의적인 증가를 보였고, 탄력성과 응집성은 유의적으로 감소하는 경향을 나타내었다. 칡즙 첨가 식빵의 관능평가 결과로 칡즙이 25% 첨가되었을 때, 최적의 배합 비율로 평가되었다. 조직감에 대한 기호도는 칡즙의 양이 증가할수록 식빵이 쫄깃쫄깃한 성질이 증가하나 입안에 붙는 듯한 느낌을 주어 15% 첨가 군에서 가장 높게 나타났다. 단맛에 대해서는 식빵의 종류나 관능검사를 실시한 사람들의 연령에 관계없이 유의적인 차이가 거의 없었다. 냄새에 대한 관능검사 결과는 식빵을 먹었을 때, 첨가된 칡즙의 양이 증가할수록 유의적으로 높게 나타났다. 칡즙과 칡즙이 25% 첨가된 식빵의 향기성분 농축물을 GC-MS로서 분리 동정하고, 칡즙의 특징적인 향기 화합물이 칡즙 첨가 식빵의 향기 화합물로 전이된 향기성분을 고찰하였다. 칡즙의 향기 화합물의 특징적인 것으로는 미생물 발효차에서 동정된 methoxy phenol 화합물들, 3-methoxy acetophenone, 녹차 등에서 동정된 ${\beta}-damascenone$, 반 발효차인 오룡차와 포종차에서 동정된 꽃 향기 성분인 benzylcyanide, 그 외 menthofuran과 coumarin 등 총 35종이 동정되었다. 칡즙 첨가 식빵의 향기 화합물은 굽기 과정의 갈변반응에 의해 생성된 구수한 향에 기여하는 pyrazine류, pyrrole류, pyridine류 20종이 동정되었고, 아울러 칡즙 첨가에 의해 전이된 methoxy phenol화합물과 benzylcyanide, ${\beta}-damascenone$, menthofuran과 coumarin 등의 총 55종이 동정되었다.

• Journal of Microbiology and Biotechnology
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• 제13권4호
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• pp.632-635
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• 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.

• 공업화학
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• 제5권2호
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• pp.189-198
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• 1994

초고진공하에서 열탈착 실험에 의하여 오산화바나듐 촉매상에서 일산화탄소와 메탄올의 홉착특성을 연구하였다. 일산화탄소는 오산화바나듐 촉매표면의 격자산소 결함을 갖는 바나듐이온이나 바나듐이온에 결합된 이중결합성 산소에 흡착하였다. 격자산소 결함을 갖는 바나듐이온에 흡착한 일산화탄소는 380K에서 탈착되었으며, 바나듐이온에 결합된 이중결합성 산소에 흡착한 일산화탄소는 격자산소와 결합하여 탄산기의 형태를 형성한 후 이산화탄소로 탈착되면서 촉매 표면을 환원시켰다. 선흡착되거나 후흡착되는 산소에 의하여, 탄산기의 형태로 흡착하는 일산화탄소의 흡착량은 증가하였다. 오산화바나듐 촉매상에서 메탄올을 흡착시킨 후 메탄올, 포름알데히드, 일산화탄소, 수소 등의 열탈착실험에 의하여 메탄올의 흡착특성을 연구하였다. 메탄올은 298 K에서 오산화바나듐 촉매상에 methoxy와 hydroxyl기를 형성하면서 분해흡착하였다.

• Archives of Pharmacal Research
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• 제27권9호
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• pp.937-943
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• 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.

• 대한화학회지
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• 제30권1호
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• pp.109-117
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• 1986

항암항생제 Daunorubicin(2a)합성단계의 최종물질인 7,9-Dideoxydaunomycinone (32)를 3-methoxybenzoic acid(5)로 부터 합성하였다. 3-methoxybenzoic acid를 4-methoxy-3-(phenylsulfonyl)-1(3H)-isobenzofuranone(11)으로 변형시킨 뒤 Hauser와 Rhee가 개발한 고리접합법을 이용하여 trimethoxynaphthoate 16을 얻은 후에 phenylsulfonylnaphthofuranone 22로 변화시킨 뒤 이 물질을 7-(ethylenedioxy)-2-octenoate(23)과 Michael형태의 반응을 전개시켜 anthracenoate 24를 얻었다. Anthracenoate을 tetracyclic 화합물 28로 바꾼뒤 ring B와 C에 붙은 methyl기들을 제거하여 7,9-Dideoxydaunomycinone(32)를 만들었다.

• Archives of Pharmacal Research
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• 제27권3호
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• pp.273-277
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• 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
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• 제18권5호
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• pp.340-345
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• 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.

• 약학회지
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• 제55권4호
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• pp.319-323
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• 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.