• Title/Summary/Keyword: 5-hydroxy-2-methyl-1

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Preparation and Thermal Properties of Poly(enaminonitriles-ester)s Derived from Dicyanovinyl-Containing Bis-Hydroxy Monomers

  • 김종태;공명선
    • Bulletin of the Korean Chemical Society
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    • v.18 no.3
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    • pp.328-333
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    • 1997
  • Dicyanovinyl-containing bis-hydroxy monomers, p-bis[1-(4-hydroxypiperidinyl)]-2,2-dicyanovinyl]benzene (2), p-bis[1-[1-(2-hydroxyethyl)piperazinyl]-2,2-dicyanovinyl]benzene (3), p-bis[1-(4-hydroxyphenylamino)-2,2-dicyanovinyl]benzene (4) and p-bis[1-[N-methyl-(N-hydroxyethyl)amino]]-2,2-dicyanovinyl]benzene (5) were prepared from p-bis(1-chloro-2,2-dicyanovinyl)benzene (1) and the corresponding amino alcohol. The poly(enaminonitriles-ester)s with a variety of chemical structures in the main chain were prepared from them. The chemical structure of polymers was confirmed through the syntheses of their corresponding model compounds. The polymers are easily soluble in polar aprotic solvents such as DMF, DMSO and NMP. Brittle and hard films can be cast from DMF solutions of polymers. Most polymers showed a large exotherm in DSC analyses and undergo a curing reaction around 350 ℃ to form insoluble materials. The polymers consisting of rigid aromatic moieties show 80-88% residual weight at 500 ℃ under nitrogen.

New Synthetic Routes to Biologically Interesting Geranylated Acetophenones from Melicope Semecarpifolia and Their Unnatural Prenylated and Farnesylated Derivatives

  • Xia, Likai;Narasimhulu, Manchala;Li, Xin;Shim, Jae-Jin;Lee, Yong-Rok
    • Bulletin of the Korean Chemical Society
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    • v.31 no.3
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    • pp.664-669
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    • 2010
  • This paper describes a new synthetic approach for biologically interesting geranylated acetophenones. The first total syntheses of 1-(5-geranyloxy-7-hydroxy-2,2-dimethyl-2H-chromen-8-yl)ethanone and 1-[5-geranyloxy-7-hydroxy-2-methyl-2-(4-methylpent-3-enyl)-2H-chromen-8-yl]ethanone, isolated from Melicope semecarpifolia, were carried out starting from commercially available 2,4,6-trihydroxyacetophenone.

Synthesis of certain N-Aryl-N'-(2-pyrimidinyl)guanidine derivatives as potential antimicrobial agents

  • Eisa, H.M.;Tayel, M.A.;Yousif, M.Y.;El-Kerdway, M.M.
    • Archives of Pharmacal Research
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    • v.13 no.1
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    • pp.78-81
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    • 1990
  • N-Aryl-N'(4-hydroxy-6-methyl-2-pyrimidinyl)guanidines (IIa-c) were prepared by cyclization of N-arybiguanides (Ia-c) with ethyl acetoacetate. Coupling of compounds (IIa-c) with the appropriate diazotized arylamine gave N-aryl-N'-(5-arylhydrazono-6-methyl-4-oxopyrimidin-2-yl) guanidines (IIIa-f). Whereas, their chlorination with phosphorus oxychloride followed by treatment of N-aryl-N'-(4-Chloro-6-methyl-2-pyrimidinyl)guanidimes (IVac) with the appropriate arylamine afforded the corresponding 4-arylamino derivatives (Vaf). Compounds (IIa-f) were also formed when compounds (1a-c) were treated with ethyl 2-arylhydrazono-3-oxobutyrates. The antimircobial testing of some of the prepared compounds against some pathogenic microorganisms revealed that only two have a marked effect against Escherichia coli.

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Metabolism of a New Neuroprotective Agent for Ischemia-Reperfusion Damage, KR-31543 in the Rats using Liquid Chromatography/Electrospray Mass Spectrometry

  • Kim, John;Ji, Hye-Young;Lee, Seung-Seok;Yoo, Sung-Eun;Kim, Sun-Ok;Lee, Dong-Ha;Lim, Hong;Lee, Hye-Suk
    • Archives of Pharmacal Research
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    • v.25 no.5
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    • pp.664-668
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    • 2002
  • KR-31543,(2S,3R,4S)-6-amino-4-[N-(4-chlorophenyl)-N-(2-methyl-2H-tetrazol-5-ylmethyl)amino]-3,4-dihydro-2-dimethoxymethyl-3-hydroxy-2-methyl-2H-1-benzopyran is a new neuroprotetive agent for ischemia-reperfusion damage. The in vitro and in vivo metabolism of KR-31543 in rats has been studied by LC-electrospray mass spectrometry. Rat liver microsomal incubation of KR-31543 in the presence of NADPH resulted in the formation of a metabolite M1. M1 was identified as N-(4-chlorophenyl)-N-(2-methyl-2H-tetrazol-5-ylmethyl)amine on the basis of LC-MS/MS analysis with the synthesized authentic standard. Rat CYP3A1 and 3A2 are the major CYP isozymes involved in the formation of M1.

Comparision of Mineral, Hydroxy Methyl Furfural Content and SDS-PAGE Pattern of Proteins in Different Honeys (다양한 꿀에 함유된 무기물 조성, Hydroxy Methyl Furfural 함량 및 꿀 단백질의 전기영동 패턴 비교)

  • Jung, Mi-Ea;Kim, Cheon-Jei;Paik, Hyun-Dong;Oh, Jae-Wook;Lee, Si-Kyung
    • Food Science of Animal Resources
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    • v.31 no.2
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    • pp.241-249
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    • 2011
  • This study was conducted to analyze ash content, mineral composition, hydroxy methyl furfural (HMF) content, stable carbon isotope ratio, and SDS-polyacrylamide gel electrophoresis patterns to investigate the quality characteristics of various honeys harvested from different sources and to identify differences useful for distinguishing honey sources. Ash content was 0.046-0.012% in acacia honey, 0.565-1.318% in chestnut honey, 0.06-0.582% in polyfloral honey, and 0.237-0.893% in native bee honey. Potassium content was high in order of chestnut honey>native bee honey>polyfloral honey>acacia honey. The Na/K ratio was 0.92-1.97 in acacia honey, 0.02-1.59 in chestnut honey, 0.02-5.30 in polyfloral honey, and 0.22-0.51 in native bee honey. The HMF content was 9.60-12.85, 10.15-25.75, 9.7-33.5, and 6.25-21.5 mg/kg in acacia, chestnut, native bee, and polyfloral honeys, respectively. HMF content was the highest in native bee honey. A 59 kDa protein band was revealed in all samples by SDS-PAGE analysis. Protein bands of 32.1, 31.9, and 33.5 kDa were revealed in some chestnut honeys, and protein bands of 32.3 and 32.5 kDa were shown in native bee honeys. A protein band of 72 kDa was also confirmed in some chestnut honeys.

Flavor Components in Mash of Takju Prepared by Different Raw Materials (원료를 달리하여 담금한 탁주 술덧의 향기성분)

  • Lee, Joo-Sun;Lee, Taik-Soo;Park, Sung-Oh;Noh, Bong-Soo
    • Korean Journal of Food Science and Technology
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    • v.28 no.2
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    • pp.316-323
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    • 1996
  • Flavor components in mash of Takju prepared by different raw materials such as nonglutinous rice, glutinous rice, barley and wheat flour were detected by GC and GC-MS method using non-polar column. Seven alcohols, 15 esters, 10 organic acids, 1 aldehyde, 4 benzenes, 3 phenols, 8 alkans, 2 ketones and 5 others were found in takju after 16 day of fermentation. takju by wheat flour had the most various components of volatile flavor. Treatment with addition starter had less flavor component than that without addition starter in takju by nonglutinous rice. Nine kinds of flavor components including acetic acid ethyl ester, 3- methyl-1-butanol, acetic acid, ethyl benzene, acetic acid 3-methyl butyl ester, 2-phenylethanol, 2,6-di-tert-butyl-4-methyl phenol. plumbagic acid and 1,2-benzenedicarboxylic acid dibutyl ester were commonly detected in all the treatments. Especially, 2,4,0-trimethyl-1,3-benzenediamine was isolated in takju that was made of nonglutinous rice without addition starter. Diethyl sulfide, 4-methoxy benzaldehyde, docosane and 2-methyl propyl octadecanoic acid were isolated from takju by nonglutinous rice with addition starter. Propionic acid ethyl ester, acetic acid butyl ester, 2-methyl butane and 3-methyl pentane were isolated from takju glutinous rice. 2-Hydroxy-4-methyl pentanoic acid and 2-methyl tridecane were isolated from akju by barley 3-(Methylthio)-1-propanol. hexanoic acid ethyl ester, butanoic acid monomethyl ester, tridecanoic acid, ethyl tetramethyl cyclopentadiene and 1,5-diaza-2,9-diketocyclotetradecane were isolated from takju by wheat flour. Major volatile flavor components were acetic acid ethyl ester, 3-methyl-1-butanol, acetic acid and 2-phenylethanol.

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Synthesis of Polybenzimidazole Containing Bulky Side Group (Bulky Side Group을 갖는 폴리벤즈이미다졸의 합성)

  • 안병현;김원호
    • 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.

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Volatile Flavor Components of Soybean Paste(Doenjang) Prepared from Different Types of Strains (균주를 달리한 된장의 향기 성분)

  • Park, Jung-Suk;Lee, Myung-Yul;Kim, Kyong-Su;Lee, Taik-Soo
    • Korean Journal of Food Science and Technology
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    • v.26 no.3
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    • pp.255-260
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    • 1994
  • Four types of soybean paste(Doenjang), using traditional meju, koji, natto meju and mixture of koji and natto meju, were manufactured and fermented for 90 days. Analyzed volatile flavor components by GC-MS were confirmed to be thirty-six components including 5 alcohols, 5 aldehydes. 8 ketones, 3 acids, 9 esters and 6 miscellaneous ones. Traditional soybean paste tested had 29 components, koji and koji-natto soybean paste $26{\sim}24$ and natto soybean paste had 20 ones. Alcohol was found to be the most abundant volatile flavor components in all samples group. Traditional soybean paste had higher ratio of carbonyl to ester than any other types of soybean paste while koji-natto soybean paste had the lowest ratio of their components. The newly identified five volatile flavor components were 3-ethoxy-l-propene, dihydro-2-methyl-3-furanone. 1-hydroxy-2-propanone, 1-(2-furanyl)ethanone and 2-acethyl ethylhexanoate.

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Synthesis of Novel 4'α-Phenyl and 5'α-Methyl Branched Carbocyclic Nucleosides

  • Oh, Chang-Hyun;Hong, Joon-Hee
    • Bulletin of the Korean Chemical Society
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    • v.26 no.10
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    • pp.1520-1524
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    • 2005
  • This paper describes the racemic and stereoselective synthetic route for a novel 4'$\alpha$-phenyl and 6'$\alpha$-methyl doubly branched carbocyclic nucleosides from an acyclic 2-hydroxy acetophenone. The installation of phenyl group at the 4'-position of carbocyclic nucleoside was successfully accomplished via a sequential [3,3]-sigmatropic rearrangement. The stereoselective introduction of a methyl group in the 6'$\alpha$-position was accomplished by Felkin-Anh controlled alkylation. Bis-vinyl 11 compound was successfully cyclized using a Grubbs’ catalyst II to desired carbocycles. The natural bases (adenine and cytosine) were efficiently coupled using a Pd(0) catalyst. Although all the synthesized compounds were examined for their activity against several viruses such as HIV-1, HSV-1, HSV-2 and HCMV, only cytosine analogues 17 exhibited weak antiviral activity against HCMV.

Synthesis of Core-Modified Porphyins and Studies of Their Temperature-dependent Tautomerism

  • 이창희;김한재;윤대위
    • Bulletin of the Korean Chemical Society
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    • v.20 no.3
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    • pp.276-280
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    • 1999
  • The different core-modified porphyrins 21-thia-23-carba-12-aza-5,10-dimesityl-15,20-diphenylporphyrin (6), and their N(12)-methyl derivatives (8) were synthesized by acid-catalyzed [3+1] condensation of the corresponding 16-thia-5,10-dimesityltripyrromethanes and 2,4-bis[(α-hydroxy-α-phenyl)methyl]pyrrole. Spectroscopic evidence indicates the existence of two different tautomeric forms at room temperature in porphyrin (6). A third form of tautomer was observed when the temperature was lowered to 223 K. The most stable tautomer is one in which the nitrogenic proton resides outside the core of the macrocycle. The ratio of the three different tautomers (outer N-H/ two inner N-H, i.e. 6/12/13) was 1/l/0.5 in the case of (6) while the ratio of 1/l/0.3 was observed in the case of (10). In the case of 21-oxa-23-carba-12-aza-5,10,15,20-tetraphenylporphyrin (7), the only stable tautomeric form observed by 1H NMR was the one that nitrogenic proton resides inside the core on