• Bulletin of the Korean Chemical Society
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• v.10 no.2
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• pp.151-154
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• 1989

4-Methoxy-4-methylcyclohexa-2,5-dienone 1 in aqueous sulfuric acid underwent the normal dienone-phenol rearrangement with methyl group migration. The fact that methyl is migrating group and methoxy is remaining group can be rationalized by the stabilization of positive charge at C-4 during the transition state. Methoxy methyl dienone 1 $((H_0)_{1/2} = - 4.6)$ is less basic than 4,4-dimethylcyclohexa-2,5-dienone whose half protonation acidity is reported as - 3.15 or - 3.66. This basicity difference comes from the unstabilization of the protonated methoxy methyl dienone 1 due to the electron withdrawing inductive effect of a methoxy group.

• Archives of Pharmacal Research
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• v.24 no.5
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• pp.402-406
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• 2001

Gas chromatographic method was investigated for the chiral separation of several $\beta$-blockeros(atenolol, betaxolol, bisoprolol, metoprolol and pindolol) using (-)-$\alpa$-methoxy-$\alpa$-(trifluoromethyl)phenylacetyl chloride as a chiral derivatizing agent for amino group. Prior to N-acylation, hydroxyl group was converted into O-silyl ethers by react with N-methyl-H-(taimethylsilyl)trifluoroacetamide. The reaction was selective and rapid and the diasteromeric derivatives were well separated by capillary gas chromatography. (R)-isomers were eluted faster than (S)-isomers when (-)-$\alpa$-methoxy-$\alpa$-(trifluoromethyl)phenylacetyl chloride was used as the chiral derivatizing agent. But in the opposite sequence when (+)-$\alpa$-methoxy-$\alpa$-(trifluoromethyl)phenylacetyl chloride was used. No racemization was found during the reaction.

• Journal of the Korean Chemical Society
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• v.58 no.6
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• pp.569-574
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• 2014

The synthesis of O-desmethylangolensin (O-DMA) analogues from methoxy-substituted benzoic acids was described. Treatment of methoxy-substituted benzoic acids with 2 equiv of ethyllithium afforded methoxypropiophenones, which were subsequently transformed to ethyl 2-(methoxyphenyl)propionates via 1,2-rearrangement of the methoxyphenyl group using $Pb(OAc)_4/HClO_4$ in triethyl orthoformate. After hydrolysis with KOH, the 2-(methoxyphenyl)propionic acids were reacted with di-2-pyridyl carbonate to afford 2-pyridyl 2-(methoxyphenyl)propionates, which were acylated with methoxy-substituted phenylmagnesium bromides to give methoxy-${\alpha}$-methyldesoxybenzoins. The methoxy groups of these compounds were selectively or fully demethylated using boron tribromide to give diverse O-DMA analogues in high yields.

• Journal of Korean Medicine Rehabilitation
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• v.18 no.1
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• pp.95-110
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• 2008

목 적 : 급성 및 만성 염증 질환은 iNOS에 의해서 생성된 과량의 NO와 관련이 있다. 따라서 이러한 질병 치료를 목적으로 NO 생성 억제물질 또는 iNOS 발현 차단물질을 개발할 가치가 있다. 본 연구는 대사 안정성을 개선시킨 dimethoxycurcumin (DiMC)이 활성화된 대식세포에서 NO 생성 및 iNOS 발현을 제어할 수 있는지 조사하였다. 방 법 : RAW264.7 세포를 DiMC (양쪽 방향성 고리에 각각 2개의 methoxy group을 가짐), curcumin (양쪽 방향성 고리에 각각 1개의 methoxy group을 가짐), bis-demethoxycurcumin (양쪽 방향성 고리에 methoxy group이 없음; BDMC) 및 tetrahydrocurcumin (양쪽 방향성 고리에 각각 1개의 methoxy group을 가지고 있지만 중앙 7개 탄소 사슬에 이중결합이 없음; THC)로 각각 전처리한 후에 LPS로 자극하였다. 이들 전처리 물질의 효과를 비교하기 위하여, NO 생성, iNOS 발현, NF-kB p65 인산화 및 p65 DNA-binding 활성을 조사하였다. 결 과 : DiMC, curcumin 및 BDMC는 NO 생성, iNOS 발현 및 NF-kB 활성을 억제하였으며, 그 세기에 있어서 DiMC가 가장 크게 관찰되었고 그 다음 curcumin 그리고 BDMC 순으로 관찰되었다. THC는 어떠한 활성도 보이지 못했다. 결 론 :DiMC는 NO 생성 억제, iNOS 발현 차단 및 NF-kB 비활성을 유도할 수 있음을 알 수 있었다. 이러한 효과는 연속된 이중결합 및 methoxy group의 증가와 관련이 있는 것으로 판단된다.

• Archives of Pharmacal Research
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• v.18 no.6
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• pp.440-448
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• 1995

Fitty two flavones were synthesized from polyoxygenated dibenzoylmethanes which were obtained by a modified Baker-Venkatarman rearrangement, of 2-benzoyl oxyacetophenones. The following flavones among them showed good cytotoxic activities against L1210 and HL60 cells ; 2'-benzoyloxy-5,7-dimethoxyflavone $(8.2{\mu}g/ml,{\;}5.0 {\mu}g/ml)$, 2'-benzyloxy-5,7,8-trimethoxyflavone $(5,9 {\mu}g/ml,{\;}11.0{\mu}g/ml,{\;}2.7{\mu}g/ml)$, 2'-hydroxy-5,7,8-trimethoxyflavone $(9.8{\mu}/ml,{\;}6.2{\mu}g/ml)$, 2'-benzyloxy-5-hydroxyflavone $(5.2 {\mu}g/ml,{\;}3.6{\mu}g/ml)$, and 5,2'-dihydroxyflavone $(5.1{\mu}g/ml,{\;}4.0{\mu}g/ml)$. Presence of 5-methoxy group potentiated the cytotoxic activity, while the existence of 7-methoxy group decreased the activity. 5-Hydroxy or methoxy activates 4-carbonyl group, while 7-methoxy group deactivates the acrbonyl group. From these observation it was concluded that the activation of carbonyl group at C-4 of a flavone is important for the enahncement of the cytotoxic activity. The presence of both 5-hydroxy and 2-benzyloxy-or 2-hydroxy group enhanced the antitumor activity; 2'-benzyloxy-5-hydroxy-7-methoxyflaone 9T/C=144%), 5.2'-dihydroxy-7-methoxyflavone (T/C=132%) and 5,2'-dihydroxy-6,78,6' trtramethoxyflvone (T/C = 172%) 2'hexanolytion of 5,2'-dihydroxy-flavones did not improve the natitumor activity; 2' hexanoyloxy-5-hydroxy-7-methoxyflavone showed T/C = 132%, about the same as that of 5,2'-dihydroxy-7-methoxyflvone (T/C=130%)

• Applied Chemistry for Engineering
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• v.10 no.8
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• pp.1169-1174
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• 1999

2-Diazo-1-naphthoquinone-5-sulfonyl chloride(NQD-Cl) was synthesized from sodium 2-diazo-naphthoquinone-5-sulfonate by chlorination. NQD-Cl was esterified with hydroxybenzophenones to give several 1,2-naphthoquinone-(2)-diazide-5-sulfonic acid ester derivatives(NQD-esters). We have compared benzophenone derivatives with methoxy group to benzophenone derivatives with hydroxy group. Solubility of each NQD-ester was studied. Each of NQD-esters was formulated with novolac base resin and PS plates were manufactured. Photosensitivity, bleachability, compatible exposed time and relative sensitivity were determined by UV spectrophotometry, imaged by UV lithographic techniques, and the gray scale method. According to the number of substituted NQD group, it showed that relative sensitivity was different from gray scale method. NQD-esters with methoxy group showed a good solubility and higher sensitivity than commercial PS ones.

• Journal of the Korean Chemical Society
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• v.39 no.8
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• pp.657-665
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• 1995

The oxidation of various benzyl ethers and benzyl alkyl ethers to benzoates has been studied in two-phase system of $CH_3CO_2Et$ and aqueous NaOCl (6.6 mol eq.). The oxidant N-oxo-4-methoxy-2,2,6,6-tetramethylpiperidium bromide (N-oxoammonium salt) was prepared in situ and recycled by addition of 4-methoxy-2,2,6,6-tetramethylpiperidine-1-oxyl (0.03 mol eq., 4-methoxy-TEMPO), co-catalyst KBr (0.03mol eq.) and second oxidant NaOCl. Thus the catalytic amount of 4-methoxy-TEMPO was used. An adjustment of the pH value of below 8.0 was also required for this reaction with 2.5 hr of reaction time at 0∼5$^{\circ}C$. Under these conditions benzyl ethers were oxidized to benzoates. The selectivity of oxidation of benzyl alkyl ethers is dependent on the acidity of hydrogen and steric effect of alkyl group.

• Journal of the Korean Chemical Society
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• v.43 no.6
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• pp.676-681
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• 1999

Itraconazole is an important drug for oral treatment of histoplasmosis and blastomycosis. ltraconazole has been the targets of many synthetic efforts due to their diverse antifungal activities. ln this study, an efficient synthetic route for Itraconazole intermediates has been developed using new procedures. Also, ltraconazole analogues introducing 2- and 3-methoxy group instead of ltraconazole intermediates with 4-methoxy group were synthesized.

• Natural Product Sciences
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• v.23 no.1
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• pp.69-74
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• 2017

A new phenol and hydrazide derivatives were obtained for the first time from the C. giganteawhite by silica gel column chromatography. The structure of the isolated compounds was identified by UV, IR NMR and MS. C. gigantea was scientifically reported for several medicinal properties viz. analgesic, antimicrobial and cytotoxic. In this screening work, anti-microbial activity of test compounds was found to be active against all organisms. Additionally, anti-inflammatory activity of the test groups has reduced the thickness of edema of the hind paw compared to the control group.

• Journal of the Korean Chemical Society
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• v.50 no.3
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• pp.183-189
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• 2006

A series of substituted styryl 4-methoxy-1-naphthyl ketones [(2E)-1-(4-methoxy-1-naphthyl)-3-phenyl-2-propen-1-ones] were synthesized using facile method of microwave assisted condensation reaction. The yield of chalcones is more than 90%. They are characterized by their physical constants, micro analysis, infrared (KBr, 4000-400 cm？1) and NMR both 1H and 13C spectral data. From infrared spectra, the s-cis and s-trans stretching vibrations of carbonyl group, from NMR spectra the ethylenic proton and carbon chemical shifts (ppm) are assigned. These spectral data are correlated with various Hammett substituent constants. From the results of statistical analysis the effect of substituents on CO, ？ and ？ proton and carbons are explained.