• Title/Summary/Keyword: Furan-3-on

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Studies on the Nuclear Magnetic Resonance Spectra of (E)-1-Aryl-3-(2- and 3-thienyl)-2-propenones and Unique Observation of 4J and 5J Coupling in Their 1H-1H COSY

  • HanLee, In-Sook;Jeon, Hyun-Ju;Lee, Chang-Kiu
    • Bulletin of the Korean Chemical Society
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    • v.32 no.2
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    • pp.687-692
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    • 2011
  • $^1H$ and $^{13}C$ NMR spectra of series of (E)-1-aryl-(2- and 3-thienyl)-2-propenones, that are aldol condensation products between 2- and 3-thiophenecarbaldehydes and m- and p-substituted acetophenones, were examined to make complete assignments of the chemical shifts. Long range couplings, $^4J$ and $^5J$, are observed in the $^1H-^1H$ COSY of both 2- and 3-thienyl compounds, which makes the elucidation of the conformation in solution possible. In contrast, the 2-furyl analogue shows the long range coupling phenomena, but the 3-furyl and phenyl analogues do not show similar phenomena.

Differential Effects of Indole, Indole-3-carbinol and Benzofuran on Several Microsomal and Cytosolic Enzyme Activities in Mouse Liver (Indole, Indole-3-calbinol 및 Benzofuran이 간장 microsome과 cytosol의 약물대사 효소 활성도에 미치는 영향)

  • Cha, Young-Nam;Thompson, David C.;Heine, Henry S.;Chung, Jin-Ho
    • The Korean Journal of Pharmacology
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    • v.21 no.1
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    • pp.1-11
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    • 1985
  • The effects of feeding indole, indole-3-carbinol and benzofuran (all at 5 mmole/kg body wt./day) on various hepatic microsomal and cytosolic enzyme activities involved in xenobiotic metabolism have been compared. Benzofuran was found to elevate the activities of many enzymes both in microsomes (e.g., aniline hydroxylase, 7-ethoxycoumarin O-deethylase, p-nitrophenol UDPGA-transferase and epoxide hydrolase) and in cytosol (e.g., glutathione reductase, glutathione S-transferase, NADH:quinone reductase and UDP-glucose dehydrogenase). The structures of indole and indole-3-carbinol are similar to benzofuran except for the substitution of nitrogen with oxygen atom within the furan ring. Results showed that the activities of UDPGA-transferase and NADH:quinone reductase were not elevated by these indole compounds. While the chemical structure of these two indole compounds are identical except for the presence of the carbinol (methanol) group in indole-3-carbinol, there were marked differences in the types and activities of microsomal enzymes that were enhanced. Among the microsomal enzyme activities determined, indole elevated only the NADPH:cytochrome c reductase, while indole-3-carbinol increased several mixed function oxidase and particularly the epoxide hydrolase activities. Based on the chemical structures of tested compounds and the observed results, possible explanations for the mechanisms involved in elevating epoxide hydrolase activity by benzofuran and indole-3-carbinol are discussed.

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Theoretical Studies on the Electrophilic Methylation of Five-Membered Heteroaromatic Compounds with Dimethylfluoronium Ion

  • Chang Kon Kim;Ikchoon Lee;Bon-Su Lee
    • Bulletin of the Korean Chemical Society
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    • v.12 no.5
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    • pp.537-540
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    • 1991
  • Electrophilic methylation reactions of five-membered heteroaromatic compounds, furan, pyrrole and thiophene, with the dimethylfluoronium ion, ${CH_3}{FCH_3}(+), have been investigated theoretically by the MNDO method. The site selectivity of ${\alpha}, {\beta}$ and heteroatom (X) is related to charge density of the site, indicating that the site selectivity is dictated by electrosatic interaction between two reaction centers. The reactivity order between the three heteroaromatics can not be determined decisively since the order differs depending on which site is compared, with relatively low activation enthalpies, ${\Delta}{H^\neq}$= 20-30 kcal/mol, in all cases. These site and substrate selectivity behaviors are consistent with the gas-phase experimental results.

Gravimetric Measurements and Theoretical Calculations of 4-Aminoantipyrine Derivatives as Corrosion Inhibitors for Mild Steel in Hydrochloric Acid Solution: Comparative Studies

  • Firas F. Sayyid;Ali M. Mustafa;Slafa I. Ibrahim;Mustafa K. Mohsin;Mahdi M. Hanoon;Mohammed H. H. Al-Kaabi;A. A. H. Kadhum;Wan Nor Roslam Wan Isahak;A. A. Al-Amiery
    • Corrosion Science and Technology
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    • v.22 no.2
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    • pp.73-89
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    • 2023
  • Due to continuous promotion of green alternatives to toxic petrochemicals by government policies, research efforts towards the development of green corrosion inhibitors have intensified recently. The objective of the current work was to develop novel green and sustainable corrosion inhibitors derived from 4-aminoantipyrine to effectively prevent corrosion of mild steel in corrosive environments. Gravimetric methods were used to investigate corrosion inhibition of 4-((furan-2-ylmethylene)amino)antipyrine (FAP) and 4-((pyridin-2-ylmethylene)amino)antipyrine (PAP) for mild steel in 1 M HCl. FAP and PAP were subjected to quantum chemical calculations using density functional theory (DFT). DFT was used to determine the mechanism of mild steel corrosion inhibition using inhibitors tested in HCl. Results demonstrated that these tested inhibitors could effectively inhibit mild steel corrosion in 1.0 M HCl. At 0.0005 M, these inhibitors' efficiencies for FAP and PAP were 93.3% and 96.5%, respectively. The Langmuir adsorption isotherm was obeyed by these inhibitors on the mild steel surface. Values of adsorption free energies, ΔGoads, revealed that FAP followed chemical and physical adsorptions.

Enantiomeric Compounds with Antileishimanial Activities from a Sponge, Plakortis sp

  • Lim, Chi-Won;Kim, Yeon-Kye;Youn, Ho-Dong;Park, Hee-Yeon
    • Journal of Applied Biological Chemistry
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    • v.49 no.1
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    • pp.21-23
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    • 2006
  • As part of a program to discover bioactive natural products from marine organisms, two new enantiomers, ent-3,6-Epidioxy-4,6,8,10-tetraethyltetradeca-7,11-dienoic acid and ent-[3,5-Diethyl-5-(2-ethyl-hex-3-enyl)-5H-furan-2-ylidene]-acetic acid methyl ether, were isolated from a sponge Plakortis sp. These compounds showed strong in vitro antiproliferative effects on promastigotes of Leishmania mexicania, flagellate protozoan that causes leishmaniasis. Structures were assumed by interpretation of NMR spectroscopic data and optical rotation. Both compounds exhibited significant antileishmanial activities in vitro with $IC_{50}$ of 1.0-23.0 ${\mu}g/ml$.

Improvement of Strength and Chemical Resistance of Silicate Polymer Concrete

  • Figovsky, Oleg;Beilin, Dmitry
    • International Journal of Concrete Structures and Materials
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    • v.3 no.2
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    • pp.97-101
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    • 2009
  • It has been known that acid-resistant concretes on the liquid glass basis have high porosity (up to 18${\sim}$20%), low strength and insufficient water resistance. Therefore they can not be used as materials for load-bearing structural elements. Significant increasing of silicate matrix strength and density was carried out by incorporation of special liquid organic alkali-soluble silicate additives, which block of superficial pores and reduces concrete shrinkage deformation. It was demonstrated that introduction of tetrafurfuryloxisilane additive sharply increases strength, durability and shock resistance of silicate polymer concrete in aggressive media. This effect is attributable to hardening of contacts between silicate binder gel globes and modification of alkaline component owing to "inoculation" of the furan radical. The optimal concrete composition with the increased strength, chemical resistance in the aggressive environments, density and crack resistance was obtained.

The Study on the Detoxification of Aflatoxin $G_1$ in Cancer Compound (발암물질인 아플라톡신 $G_1$의 탈독소화 반응에 관한 연구)

  • 장향동;김래현;이수경
    • Journal of the Korean Society of Safety
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    • v.11 no.4
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    • pp.84-89
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    • 1996
  • The Oxidation of aflatoxin $G_1$ ($AFG_1$) with ozone in chloroform solvent gave the stable ozonide into ozonization of the double bond in the terminal furan ring, and this reaction have been carried out for 3hr at -78. 5$^{\circ}C$. The chloroform solvent was removed in a stream of nitrogen and the residue was separated by elution chromatography(EC). The structure of this compound have been identified by using MS, $^1H-NMR$, $^l3C-NMR$ and I. R spectroscopy, respectively. This compound was formed the normal stable AFG$_1$-ozonide into spontaneous rearrangement after unstable ozonide according to sigmatropic rearrange ment dependent upon cyclo addition by ozone.

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Melanin Biosynthesis Inhibitors from the Tubers of Gastrodia elata

  • Li Gao;Kim, Jae-Hyon;Xu, Ming-Lu;Seo, Chang-Seob;Kim, Hyo-Jin;Lee, You-Jeong;Lee, Yeun-Koung;Lee, Seung-Ho;Chang, Hyeun-Wook;Son, Jong-Keun
    • Proceedings of the PSK Conference
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    • 2003.10b
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    • pp.206.3-207
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    • 2003
  • The bioassay-guided fractionation of the methylene chloride soluble portion of a methanol extract of Gastrodia elata tubers led to the isolation of a new furfural, 5-(4-hydroxy-benzyloxymethyl)-furan-2-carbaldehyde (2), together with four known compounds (1, 3-5), which exhibited potent inhibitory activity at the concentration of 25 $\mu\textrm{g}$/ml on melanin biosynthesis in cultured B-16 mouse melanoma cells.

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Changes in the Organic Compounds and Molecular Weight Distribution in Pig Wastewater by Each Treatment Steps. (양돈폐수의 정화처리 과정별 유기물질 성분과 분자량 분포 변화 연구)

  • 최희철;이덕수;권두중;강희설;유용희;연규영;최영수;곽정훈;최동윤
    • Journal of Animal Environmental Science
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    • v.10 no.1
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    • pp.29-36
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    • 2004
  • These experiments were conducted to analyze the characteristics of organic compounds and molecular weight distribution according to the treatment steps of purifying system for pig wastewater. The results obtained are summarized as follow. 1. Raw pig wastewater contained 31 kinds of organic compounds such as acetic acid, 2-butanone, hexane, chloroform, propionic acid, butanoic acid etc. 2. After ozone treatment, 13 kinds of organic compounds such as ethene, pentane, 2-methylopropanal, hexane, furan and so on were detected in the wastewater. 3. After $TiO_2$ treatment, 12 kinds of organic compounds such as ethene, hexane, chloroform, 1-decene, silane and so on were detected from the effluent. 4. After both ozone and $TiO_2$ treatment, portion of molecular weight smaller than 500 Daltons and molecular weight between 500 to 1,000 Daltons in the wastewater increased.

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A Comparative Study on Green Liquor Pre-Pulping Extraction of Mixed Hardwood Chips (혼합 하드우드 칩으로부터 녹액(Green Liqour)선-펄핑추출 공정에 관한 연구)

  • Um, Byung-Hwan
    • Korean Chemical Engineering Research
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    • v.51 no.5
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    • pp.561-567
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    • 2013
  • Mixed hardwood chips were pre-pulping extracted with green liquor prior to kraft pulping in order to recover hemicelluloses for use as biofuels. This green liquor solution containing mainly sodium sulfide and sodium carbonate was applied at different alkali charges (expressed as $Na_2O$) of 0, 1, 3, and 5% on dry wood weight. The extractions were performed at $160^{\circ}C$ for residence times ranging from about 1-2 h to determine the effect of extraction severity on composition of the pre-pulping extract. The severity of hemicellulose extraction time and green liquor charge controls the concentration of acetic acid and monosaccharide sugars available for downstream processing, the accumulation of degradation products such as organic acids and furans in the extract. As the alkali charge was increased, the amount of acetate side chains on the hemicelluloses and the dissolved lignin in the extract increased but the carbohydrate and sugars in the extract decreased appreciably. Hot water extraction (0% alkali addition) released the greatest amount of carbohydrates, up to 29.80 g/L measured as component sugars, but resulted in the greatest decrease in pulp yield. Meanwhile, pre-pulping extraction with 3% green liquor increased the pulp yield while greatly reducing the component sugars to 7.08 g/L. Fundamental data obtained in this study will allow selection of optimum hemicellulose extraction conditions for integrating the extraction operation into the Kraft pulping process.