• Title/Summary/Keyword: Ketone ester

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cis-trans Isomeric and Substituent Effects on the Lanthanide Induced Shifts in 2-Phenylcyclopropanic System

  • So, Jung-Ho;Cho, Nam-Sook
    • Bulletin of the Korean Chemical Society
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    • v.5 no.6
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    • pp.226-230
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    • 1984
  • LIS's of cis and trans-methyl-2-phenylcyclopropanecarboxylate, cis and trans-t-butyl-2-phenylcyclopropanecarboxylate, cis and trans-N,N-dimethylcyclopropanecarboxamide, trans-2-phenylcyclopropyl methyl ketone and trans-2-phenylcyclopropyl t-butyl ketone have been studied. The LIS's hold the McConnell-Robertson relation and are mainly influenced by the steric effect. LIS's of trans isomers are larger than those of cis isomers. In trans isomers, the LIS's decrease in the following order: methyl ketone > methyl ester > N,N-dimethyl amide > t-butyl ketone${\sim}$t-butyl ester.

Reactivity of 7-Dithiocarboxy-imidazo [2,1-b]thiazolium-betnine with Aliphatic Alkylating Agents

  • Song, Jung-Wha;Suh, Myung-Eun;Yoo, Kyung-Ho;Park, Sang-Woo
    • Archives of Pharmacal Research
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    • v.12 no.1
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    • pp.17-21
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    • 1989
  • We have reported earlier on the reactivity of 7-dithiocarboxy-3-phenyl-5,6-dihydro imidazo[2,1-b]thiazolium-betaine with several para-substituted phenacyl bromides. In this work reactions of 7-dithiocarboxy-3-phenyl(or methyl)-5,6-dihydro imidazo[2,1-b]thiazolium-betaine with a series of aliphatic alkylating agents of ${\alpha}$ -halo ketone,${\gamma}$-halo koto ester and ${\alpha}$ -halo ester were examined for the similar purpose. In case of ${\alpha}$-halo ketone or ${\gamma}$-halo koto ester such as ${\alpha}$ -chloro acetone or ethyl 4-chloro acetoacetate new biheterocyclic compound was obtained via ring transformation reaction. However, reaction of the betaine with methyl(or ethyl) bromoacetate used as a ${\alpha}$-halo ester, gave, in-stead, S-alkylated quarternary ammonium salt.

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Studies on Triterpenoid Corticomimetics (V) - Oxidation of Presenegenin with Chromium Trioxide-Acetic Acid to Yield 11-Keto and 12-Keto Derivatives

  • Han, Byung-Hoon;Han, Yong-Nam
    • Archives of Pharmacal Research
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    • v.8 no.4
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    • pp.229-236
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    • 1985
  • Oxidation of presenegenin dimethyl ester triacetate with chromium trioxide in acetic acid yielded two compounds, 11-ketone (IV) and 12-ketone (IV) derivatives. The latter was a main product. On mild alkaline hydrolysis, IV afforded 11-keto-presenegenin dimethyl ester (V), mp 232-$234^{\circ}$, $C_{32}H_{48}O_{8}$, whereas VI did 12-keto-presenegenin dimethyl ester 12, 27-hemiketal (VIII), mp 240-$242^{\circ}$, $C_{32}H_{50}O_{8}$.

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Ketone ester supplementation of Atkins-type diet prolongs survival in an orthotopic xenograft model of glioblastoma

  • Hassan Azari;Angela Poff;Dominic D'Agostino;Brent Reynolds
    • Anatomy and Cell Biology
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    • v.57 no.1
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    • pp.97-104
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    • 2024
  • Heavy reliance on glucose metabolism and a reduced capacity to use ketone bodies makes glioblastoma (GBM) a promising candidate for ketone-based therapies. Ketogenic diet (KD) is well-known for its promising effects in controlling tumor growth in GBM. Moreover, synthetic ketone ester (KE) has demonstrated to increase blood ketone levels and enhance animal survival in a metastatic VM-M3 murine tumor model. Here, we compared the efficacy of a KE-supplemented Atkins-type diet (ATD-KE) to a classic KD in controlling tumor progression and enhancing survival in a clinically relevant orthotopic patient-derived xenograft GBM model. Our findings demonstrate that ATD-KE preserves body weight (percent change from the baseline; 112±2.99 vs. 116.9±2.52 and 104.8±3.67), decreases blood glucose (80.55±0.86 vs. 118.6±9.51 and 52.35±3.89 mg/dl), and increases ketone bodies in blood (1.15±0.03 mM vs. 0.55±0.04 and 2.66±0.21 mM) and brain tumor tissue (3.35±0.30 mM vs. 2.04±0.3 and 4.25±0.25 mM) comparable to the KD (results presented for ATD-KE vs. standard diet [STD] and KD, respectively). Importantly, the ATD-KE treatment significantly enhanced survival compared to the STD and was indistinguishable from the KD (47 days in STD vs. 56 days in KD and ATD-KE), suggesting that a nutritionally balanced low carbohydrate ATD combined with KE may be as effective as the KD alone in reducing brain tumor progression. Overall, these data support the rationale for clinical testing of KE-supplemented low-carb diet as an adjunct treatment for brain tumor patients.

Synthesis of Quinazoline 4-one Drvivatives from 2-Aminobenzamide(II) - Reaction with $\gamma$-Lactone and Diketone (2-Aminobenzamide로부터 Quinazoline 4-one 유도체의 합성 (II) - $\gamma$-락톤과 디케톤과의 반응)

  • 서명은
    • YAKHAK HOEJI
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    • v.30 no.5
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    • pp.203-207
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    • 1986
  • 2-Aminobenzamide reacts with not only keton radical but also carbonyl group in carboxylic acid, to form easily -N-C-N-novel ring cyclization as a result I and V. In addition, it reacts with 1, 2-cyclohexadione or benzil, whitch are both 1, 2-diketone compounds, at the both ketone radical sites to give V or VII respectively. On the reaction with dimethone, however, which has 1, 3-diketone radical, it reacted with only one carbanyl group and VI was produced. We investigated the reaction with cr-ketoester such as ethyl pyruvate and diethyl rnesoxalate. In the reaction with ethylpyruvate, amine group in 2-aminobenzamide reacted not with ketone radical but carbonyl group in ester (product VIII). On the other hand, diethyl measoxalate reacted at the ketone radical site rather than the ester site (product IX).

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The Synthesis of 2-Furyltriisopropoxytitanium and its Reactivity to Carbonyl Compounds (2-Furytriisopropoxytitanium의 합성 및 카르보닐 화합물에 대한 반응성)

  • Koo, Doo-Hyo;Kyung, Suk-Hun
    • Applied Biological Chemistry
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    • v.39 no.4
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    • pp.309-314
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    • 1996
  • 2-Furyltriisopropoxytitanium was synthesized in situ through transmetallation of 2-furyllithium with chlorotitaniumtriisopropoxide. The compound could be isolated at room temperature and preserved at $-10^{\circ}C$ for several weeks. The reactivity 2-furyltriisopropoxytitanium to carbonyl compounds proved to be high. A complete aldehyde selectivity was observed in competition reactions of 2-furyltriisopropoxytitanium with a 1:1 mixture of aldehyde and ketone. In competition reactions of 2-furyltriisopropoxytitanium with a 1 : 1 mixture of ketone and ketone, the degree of ketone / ketone discrimination was substantial. In the reaction of 2-furyltriisopropoxytitanium to ketone-ester function, the reagent was solely reacted with the ketone function.

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MPV-Reduction of C=O bond with Al-substituted-dialkylalan; A Theoretical Study on Relative Reactivity of Various Carbonyl Substrates

  • Nahm, Keepyung
    • Bulletin of the Korean Chemical Society
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    • v.35 no.2
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    • pp.546-550
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    • 2014
  • Relative reactivity of various carbonyl and acid derivatives in MPV-type (Meerwein-Ponndorf-Verley) reduction with an DIBAL(F) model has been studied via DFT and MP2 methods. Free energies of initial adduct formation (-Gadd) of DIBAL(F) model and carbonyls are in the order of amide < ester < aldehyde < ketone < acid chloride; in the alan-amide adduct, the developed positive charge at carbonyl carbon is expected to be stabilized by amide resonance, but in the acid chloride adduct it is destabilized by inductive effect of chloride. However the TS barrier energies (${\Delta}G_{TS}$) for the MPV-type hydride reduction of the carbonyl adducts are in the order of aldehyde < ketone < acid chloride << ester < amide; presumably decreasing order of electrophilicity of carbonyl carbon at adducts, which is well correlated with experimental data. It is noted that the relative reactivity of carbonyl derivatives in MPV-type reduction with DIBAL(X) is not governed by the alan-adduct formation energies, but follows the order of electrophilicity of carbonyl carbon of transition states.

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

  • Fukui, Tetsuya
    • Proceedings of the PSK Conference
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    • 2003.10a
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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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Separation and Identification of Volatile Components of Apple Fruits after Harvest (수획후(收獲後) 사과과실(果實)의 향기성분(香氣成分)의 분리(分離) 및 동정(同定))

  • Kim, Sung-Dal;Odagiri, Satoshi;Ito, Tetsuo
    • Applied Biological Chemistry
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    • v.32 no.2
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    • pp.143-147
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    • 1989
  • The volatile compounds of McIntosh apples were separated and identified at the stage of climacteric maximum. 21 compounds were identified from head space method and classes of that were 13 kinds of esters, 6 of alcohols, an aldehyde and a ketone. From simultaneous steam distillation-extraction method, 37 compounds were identified and classes of that were 20 kinds of esters, 14 of alcohols, 2 of aldehydes and a ketone. Esters were the most abundant flavor component in the both methods and next was alcohols.

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