• 제목/요약/키워드: Acetoacetate

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1,4-디하이드로피리딘 산류의 합성 (Synthesis of 1,4-Dihydropyridine Carboxylic Acids)

  • 서정진;홍유화
    • 약학회지
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    • 제33권2호
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    • pp.80-86
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    • 1989
  • 2,6-Dimethyl-4-(3'-nitrophenyl)-1,4-dihydropyridine-3,5-dicarboxylic acid 3-methyl 5-(2'-phenylsulfinyl) ethyl ester (10) or 2,6-Dimethyl-4-(2' or 3'-nitrophenyl)-1,4-dihydropyridine-3,5-dicarboxylic acid 3-alkyl 5-(2-methylsulfonyl) ethyl ester (14a, b, c) were hydrolyzed by treatment with NaOH in aqueous EtOH solution to give 2,6-Dimethyl-4-(3'-nitrophenyl)-1,4-dihydropyridine-3,5-dicarboxylic acid monomethyl ester (4b), 2,6-Dimethyl-4-(2'-nitrophenyl)-1,4-dihydropyridine-3,5-dicarboxylic acid monomethyl ester (4c) and 2,6-Dimethyl-4-(2'-nitrophenyl)-1,4-dihydropyridine-3,5-dicarboxylic acid monoisopropyl ester (4d) in 80 -90% yield. By the same procedure, 2,6-Dimethyl-4-(3'-nitrophenyl)-1,4-dihydropyridine-3,5-dicarboxylic acid 3,5-bis (2'-methylsulfonyl) ethyl ester (15) gave 2,6-Dimethyl-4-(3'-nitrophenyl)-1,4-dihydropyridine-3,5-dicarboxylic acid (4e) in 96% yield.

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Acetoacetyl-CoA Synthetase, a Novel Cytosolic Ketone Body-Utilizing Enzyme that Specifically Activates Acetoacetate to its Coenzyme A Ester

  • Fukui, Tetsuya
    • 대한약학회:학술대회논문집
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    • 대한약학회 2003년도 Proceedings of the Convention of the Pharmaceutical Society of Korea Vol.2-1
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    • pp.70-70
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    • 2003
  • In mammalians, ketone bodies (acetoacetate, D(-)-3-hydroxybutyrate and acetone) are generated mainly in the liver via the 3-hydroxy-3-methylglutaryl-CoA pathway, carried to and utilized in extrahepatic tissues as an energy source during starvation and diabetes in particular due to their overproduction as the consequence of elevated fatty acid oxidation and lowered glucose metabolism. (omitted)

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CuI Nanoparticles as New, Efficient and Reusable Catalyst for the One-pot Synthesis of 1,4-Dihydropyridines

  • Safaei-Ghomi, Javad;Ziarati, Abolfazl;Teymuri, Raheleh
    • Bulletin of the Korean Chemical Society
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    • 제33권8호
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    • pp.2679-2682
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    • 2012
  • A simple one-pot synthesis of two derivatives of 1,4-dihydropyridines has been described under reflux conditions using copper iodide nanoparticles (CuI NPs) as a catalyst in high yields. This method demonstrated four-component coupling reactions of aldehydes and ammonium acetate via two pathways. In one route, the reaction was performed using 2 eq ethyl acetoacetate while in the other one 1 eq ethyl acetoacetate and 1 eq malononitrile were used. The CuI NPs was reused and recycled without any loss of activity and product yield. It is noteworthy to state that wide range of the 1,4-dihydropyridines have attracted large interest due to pharmacological and biological activities.

Simultaneous Determination of Plasma Lactate, Pyruvate, and Ketone Bodies following tert-Butyldimethylsilyl Derivatization using GC-MS-SIM

  • Yoon, Hye-Ran
    • 대한의생명과학회지
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    • 제21권4호
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    • pp.241-247
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    • 2015
  • Lactate and ketone bodies are considered biological markers for ketosis and several inherited metabolic disorders. In the current study, the specific ratios of lactate and ketone bodies as analytical tools for differential diagnosis of various lactic acidosis were devised. The study included a protein precipitation step following tert-butyldimethylsilyl derivatisation. Total run time was approximately 30 min including sample preparation and GS/MS analysis. The limits of detection were below 0.1 pg/mL over the targeted 4 analytes. The calibration curve was linear over the concentration range of $0.001{\sim}250{\mu}g/mL$ for pyruvate, beta-hydroxybutyrate, and acetoacetate ($R^2$ > 0.99). Inter-day accuracy and precision were 87.7~94.8% with RSD of 2.5~5.7% at 2 levels. Absolute recoveries (%) of target analytes were 87.0~98.4%. The method was validated for the quantification of lactate and ketone bodies for differentiation of lactic acidosis.

에틸 아세토아세테이트 토토머리즘 평형 상수의 밀도 의존성 (The Effect of Solvent Density on the Ethyl Acetoaceate Tautomerism)

  • 박윤국
    • 공업화학
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    • 제17권3호
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    • pp.291-295
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    • 2006
  • 본 연구에서는 아임계 및 초임계 이산화탄소하의 에틸 아세토아세테이트의 케토-에놀 토토머릭 평형상수를 후리에 적외선 분광기를 이용하여 세 가지 다른 온도에서 측정하였다. 케토-에놀 토토머릭 평형상수의 용매에 대한 밀도 의존성을 연구하기 위하여 정온하에서 이산화탄소의 압력을 변화시켰다. 용매인 이산화탄소의 밀도를 증가 시키면, 케토 토토머의 양이 증가하게 되어 케토-에놀 토토머릭 평형상수값이 감소한다. 에틸 아세토아세테이트의 케토-에놀 토토머릭 평형상수의 밀도의존성을 연구하기 위하여 변형된 격자유체수소결합 모델을 적용하였다.

성별 및 채뇨 시각별 $^1H$ NMR 기반 뇨 대사체 프로파일링 연구 ($^1H$ NMR-Based Urinary Metabolic Profiling of Gender and Diurnal Variation in Healthy Korean Subjects)

  • 정진영;황금숙;박종철;김동현;하미나
    • Environmental Analysis Health and Toxicology
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    • 제25권4호
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    • pp.295-306
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    • 2010
  • Objectives : This study was undertaken to examine the metabolomic changes due to gender and diurnal variation at sampling time and to identify an appropriate time point for urine sampling in epidemiologic studies using metabolomic profiles. Methods : Urine samples were collected twice a day (morning and afternoon) from 20 healthy Korean adults after fasting for 8 hours. The metabolomic assay was investigated using $^1H$ NMR spectroscopy coupled with the principal components analysis (PCA) and partial least squares discriminant analysis (PLS-DA). The metabolites responsible for differentiation between groups were identified through the loading plot of PLS-DA and quantified using Chenomx NMR Suite with a 600 MHz library. Results : Metabolites responsible for differentiation in gender and sampling time were creatinine, trimethyl anine oxide (TMAO), hippurate, mannitol, citrate and acetoacetate. Dimethylamine showed difference only as a factor of diurnal time. The level of creatinine was higher in men compared to women, and the levels of citrate, TMAO, hippurate, mannitol, and acetoacetate were higher in women compared to men. The levels of creatinine, TMAO, hippurate, dimethylamine and mannitol were higher in the morning rather than the afternoon while those of citrate and acetoacetate were higher in the afternoon rather than the morning. Conclusions : Since urinary metabolomic profiles varied by gender and diurnal cycle, urine sampling should be performed at the same time point for all participants in epidemiologic studies using metabolomic profiles.

Synthesis of Heterocyclic Quinones Containing Bridgehead Nitrogen Atom from 2-Aminonaphtho[2,3-d]thiazole-4,9-dione

  • Fandy, Ragab F.
    • Archives of Pharmacal Research
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    • 제23권5호
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    • pp.446-449
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    • 2000
  • Imidazonaphthothiazole derivatives 3∼6 were prepared by treatment of 2-aminonaphtho[2,3-d]-thiazole-4,9-dione(1) with phenacyl bromide, chloroacetic acid, diethyl oxalate and 2,3-dichloroquinoxaline respectively. The reaction of 1 with ethyl acrylate, ethyl acetoacetate and diethyl malonate gave the corresponding naphthothiazolopyrimidine derivatives 8∼11.

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Synthesis of novel Heterocycles Through Reaction of Indolin-2-one Derivatives with Active Methylene and Amino Reagents

  • Abdel-Latif, F.F.;Ahmed, E.Kh.;Mekheimer, R.;Mashaly, M.M.
    • Archives of Pharmacal Research
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    • 제20권5호
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    • pp.507-509
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    • 1997
  • Several new spiro compounds were synthesized via one-pot ternary condensation of isatin, malononitrile and each of thiobarbituric acid, barbituric, 3-methyl-pyrazolin-5-one, 1-phenyl-3-methyl-pyrazolin-5-one, acetylacetone, benzoylacetone, ethyl acetoacetate, phenacyl cyanide or ethyl-cyanoacetate dimer. Structures and reaction mechanisms were reported and supported via a second synthetic route.

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Mn(III)-Mediated Radical Cyclization for Δ1-3-Octalone Synthesis

  • Lee, Mi-Ai;Yang, Jae-Deuk;Kim, Moon-Soo;Jeon, Hye-Sun;Baik, Woon-Phil;Koo, Sang-Ho
    • Bulletin of the Korean Chemical Society
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    • 제23권5호
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    • pp.736-740
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    • 2002
  • An efficient and practical synthetic method of △1 -3-octalone, which is a versatile building block for thesyntheses of polycyclic compounds, has been developed. The dianion of ethyl acetoacetate reacts with cyclohexene-1-carboxaldehyde (3) to produce the aldol adduct 6, which then undergoes Mn(Ⅲ)-mediated radical cyclization followed by acetate elimination to give △1 -3-octalone 4. A detailed mechanistic insight of Mn(Ⅲ)-mediated cyclization of 6 has been disclosed.