• Title/Summary/Keyword: ester synthesis

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Synthesis of Trifluoromethylated Dihydro-1,4-oxathiin Carboxanilides and Their Fungicidal Activity (삼불화메틸기가 포함된 디히드로-1,4-옥사티인 카르복스아닐리드 유도체의 합성과 살균 활성)

  • Nam, Kee-Dal;Kim, Jin-Cheol;Cho, Kwang-Yun;Hahn, Hoh-Gyu
    • Applied Biological Chemistry
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    • v.44 no.3
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    • pp.191-196
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    • 2001
  • ${\alpha},{\beta}$-Unsaturated carboxanilides 5 with trifluromethylated dihydro-1,4-oxathiins were synthesized for the development of new agrochemical fungicide. Chlorination of trifluoromethylated ${\beta}-keto$ ester 6 followed by the reaction with 1,2-mercaptoethanol gave intermediate 1,4-oxathiane 11. Without purification of 11, substitution of hydroxy group by chlorine, followed by dehydrochlorination of 10 in the presence of triethylamine afforded trifluoromethylated dihydro-1,4-oxathiin ethyl ester 9. Acylation of the hydroxy group of the carboxylic acid 12 followed by treatment of various amines gave the corresponding trifluoromethylated dihydro-1,4-oxathiin carboxamides 5. Antifungal screening (in vivo) of the synthesized compounds against typical plant diseases, which include rice blast, rice sheath blight, cucumber gray mold, tomato late blight, wheat leaf rust, and barley powdery mildew, was carried out. Where meta position of the phenyl group was substituted with isopropoxy or isopropyl group, excellent antifungal activities against rice sheath blight and wheat leaf rust were detected.

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A Study on Structure Aanalysis and Synthesis of Polyester Polyol & Polyurethane (폴리에스터 폴리올과 폴리우레탄의 합성과 구조분석에 대한 연구)

  • Jin, Kyung Ho;Cho, Ur Ryong
    • Elastomers and Composites
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    • v.49 no.1
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    • pp.31-36
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    • 2014
  • Polyester polyols were synthesized by using each one mole of sebacic acid, isophthalic acid, ethylene glycol, and neopentyl glycol. The synthesized polyol had 56.6 mg KOH/g of hydroxy value and 1980 g/mole of molecular weight. From FT-IR structure analysis of polyester polyol, Hydroxy group(-OH) was observed around 3600 $cm^{-1}$, -CH shoulder of sebacic acid at 2950 $cm^{-1}$, carbony group of ester around 1730 $cm^{-1}$, and benzene ring of isophthalic ring was represented at 1600 $cm^{-1}$, 740 $cm^{-1}$. In case of polyurethane, hydroxy peak was showed at 3600 $cm^{-1}$, and -NH group around 3300 $cm^{-1}$, 1530 $cm^{-1}$. From $^1H$ NMR measurement of polyester polyol, it was found that sebacic acid was represented at 1.3, 1.5, 2.1 ppm, isophthalic acid at 7.3, 8.1, 8.7 ppm, ethylene glycol at 4.2 ppm, and neopentyl glycol at 0.8, 3.2, 3.9 ppm, respectively. In the polyurethane, it is almost the same as spectrum of polyester polyol, but showed very week peak at 7 ppm by benzene ring of toluene diisocyanate.

The Convergence Effect of Phloretin Existent in Plants on Vascular Contractility (플로레틴(Phloretin)의 혈관내피수축 융합효과와 관련기전 연구)

  • Bang, Joon Seok;Je, Hyun Dong;Min, Young Sil
    • Journal of Convergence for Information Technology
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    • v.10 no.10
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    • pp.143-149
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    • 2020
  • This study tried to observe the ability to inhibit vasocontriction in phloretin - the primary ingredient of apple tree leaves and the Manchurian apricot - through ROCK(Rho-associdated, coiled-coil containing protein kinase) inactivation in rat aortae. A piece of artery that was separated from Sprague-Dawley male rats and retained or damaged the endothelium was suspended in myograph tank with two metal rings, the lower ring fixed to the bottom of the tank, and the upper ring connected to the isotonic force transducer. Interestingly, phloretin inhibited fluoride- or phorbol ester-provoked contraction implying that additional pathways dissimilar from endothelial nitric oxide synthesis such as ROCK or MEK (mitogen activated protein kinase kinase) inactivation might be involved in the vasorelaxation. Therefore, this study provides that phloretin participates in the reduction of ROCK or MEK activity in smooth muscle in addition to the endothelial-dependent action of the endotheliuim in complete blood vessels, and consequently inhibits actin-myosin interaction in smooth muscle. Furthermore, phloretin inhibited thromboxane A2-induced contraction suggesting the mechanism including inhibition of ROCK and MEK.

Induction of Disease Resistance by Acibenzolar-S-methyl, the Plant Activator against Gray Mold (Botrytis cinerea) in Tomato Seedlings (저항성 유도물질(acibenzolar-S-methyl)처리에 의한 토마토 잿빛곰팡이병 발병억제)

  • Lee Jung-Sup;Kang Nam-Jun;Seo Sang-Tae;Han Kyoung-Suk;Park Jong-Han;Jang Han-Ik
    • Research in Plant Disease
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    • v.12 no.1
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    • pp.40-45
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    • 2006
  • The plant defence activator, Acibenzolar-S-methyl [benzo (1,2,3) thiadiazole-7-carbothioic acid-S-methyl ester, ASM] was assayed on tomato seedlings for its ability to induce resistance against Botrytis cinerea, the causal agent of gray mold in tomato. Pre-treatment of plants with ASM reduced the severity of the disease as well as the growth of the mycelium in plants. In ASM treated plants, reduction in disease severity (up to 55%) was correlated with suppression of mycelia growth (up to 46.5%) during the time course of infection. In plants treated with ASM, activities of peroxidase were determined as markers of resistance. Applications of ASM induced Progressive and significant increase of the enzyme in locally treated tissues. Such responses were expressed earlier and with a much higher magnitude when ASM-treated seedlings were challenged with the pathogen, thus providing support to the concept that a signal produced by the pathogen is essential for triggering enhanced synthesis and accumulation of the enzymes. No such activities were observed in water-treated control plants. Therefore, the slower symptom development and reduction in mycelium growth in ASM treated plants might be due to the increase in activity of oxidative and antioxidative protection systems in plants.

Preparation and Properties of DMF-Based Polyurethanes Containing Bio-Polyol/Ester-Polyol for Wet-Type Polyurethane Artificial Leather (습식 인조피혁용 바이오 폴리올/폴리에스터 폴리올을 함유한 DMF 기반 폴리우레탄의 제조 및 물성)

  • Sur, Suk-Hun;Choi, Pil-Jun;Ko, Jae-Wang;Park, Ji-Hyeon;Lee, Jae-Yeon;Lee, Young-Hee;Kim, Han-Do
    • Clean Technology
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    • v.25 no.1
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    • pp.7-13
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    • 2019
  • Recently, attention has been paid to obtaining bio-polyols from renewable resources. Successful use of these natural ingredients successfully produced in the industry for the synthesis of various polyurethanes is a very important task. In this study, a series of dimethylformamide (DMF) based polyurethanes were synthesized from methylene diphenyl diisocyanate (MDI)/1, 4-butanediol and bio-polyol (polytrimethylene ether glycol based on 1, 3-propanediol : B-POL)/polyester polyol (polyadipate diol based on 1,4-butandiol : H-PET). The effect of different ratio of bio-polyol (B-POL)/polyester polyol (H-PET) on the physical properties of polyurethane was investigated. As the B-POL content in B-POL/H-PET mixture increased, the glass transition of soft segment (Tgs) and tensile strength of polyurethane decreased, however, the elongation at break and tear strength increased. On the other hand, artificial leather was produced by wet process using synthesized DMF-based polyurethanes. It was found that there was almost no difference in the effect of the B-POL/H-PET composition on the average size and density (the number of cells per unit volume) of the porous cells formed in artificial leather. These results show that there is no problem in using bio-polyol (B-POL) based polyurethane for artificial leather produced by wet process.

Synthesis and Plasticity of Cyclic Ester Compounds Using Fatty Acids (지방산을 이용한 고리형 에스터 화합물의 합성 및 그의 가소 특성 연구)

  • Han-Na Lee;Hye-Jin Jang;Je-Wan Woo
    • Applied Chemistry for Engineering
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    • v.34 no.3
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    • pp.252-257
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    • 2023
  • In this study, to replace phthalate-based plasticizers known as endocrine disruptors, compounds as plasticizer candidates were synthesized by using alcohols containing rings and fatty acids extracted from animal and vegetable oils, and their properties as plasticizers, including their plasticization efficiency, were evaluated. Nine compounds synthesized by esterification of fatty acids (caprylic acid, capric acid, lauric acid) and alcohols (solketal, benzyl alcohol, cyclohexanol) were identified by 1H-NMR. The nine synthetic compounds were evaluated for their plasticity by adding them to PVC resin, and compared with the commercial plasticizers DEHP, DINCH, and ESO. According to the results, plasticization efficiency was 0.96 to 1.02 times higher than DEHP, 0.94 to 0.98 times higher than ESO, and 1.05 to 1.10 times higher than DINCH. Thermal stability was somewhat lower than that of DEHP and DINCH, but showed better results than ESO. The results of the solvent extraction test showed that both aqueous and oily solvents showed higher values than DEHP and DINCH but showed similar or superior properties to ESO.

The Effect of Hydrogen Peroxide on Inducible Nitric Oxide Synthase Expression in Murine Macrophage RA W264.7 Cells (Murine macrophage RAW264.7에서 과산화수소가 유발형 산화질소 합성효소의 발현에 미치는 영향)

  • Ahn, Joong-Hyun;Song, Jeong-Sup
    • Tuberculosis and Respiratory Diseases
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    • v.47 no.2
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    • pp.172-183
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    • 1999
  • Background: Nitric oxide is a short-lived effector molecule derived from L-arginine by the nitric oxide synthase(NOS). Nitric oxide plays a role in a number of physiologic and pathophysiologic functions including host defense, edema formation, and regulation of smooth muscle tone. Some kinds of cells including macrophage are known to produce large quantities of nitric oxide in response to inflammatory stimuli such as interleukin-$1\beta$(IL-$1\beta$), tumor necrosis factor-$\alpha$(TNF-$\alpha$), interferon-$\gamma$(IFN-$\gamma$) and lipopolysaccharide(LPS). Reactive oxygen species are also known to be important in the pathogenesis of acute cell and tissue injury such as acute lung injury model Methods: Using the RA W264.7 cells, we have examined the ability of oxidant hydrogen peroxide($H_2O_2$) to stimulate nitric oxide production and inducible NOS mRNA expression. Also, we have examined the effects of NOS inhibitors and antioxidants on $H_2O_2$ induced nitric oxide production. Results: Stimulation of RAW264.7 cells with combinations of 100 ng/ml IL-$1\beta$, 100 ng/ml TNF-$\alpha$, and 100 U/ml IFN-$\gamma$ or 100 U/ml IFN-$\gamma$ and $1{\mu}g/ml$ LPS induced the synthesis of nitric oxide as measured by the oxidation products nitrite($NO_2^-$) and nitrate($NO_3^-$). Addition of $250 {\mu}M-2$ mM $H_2O_2$ to the cytokines significantly augmented the synthesis of $NO_2^-$ and $NO_3^-$(p<0.05). When cells were incubated with increasing concentrations of $H_2O_2$ in the presence of IL-$1\beta$, TNF-$\alpha$ and IFN-$\gamma$ at constant level, the synthesis of $NO_2^-$ and $NO_3^-$ was dose-dependently increased(p<0.05). $N^G$-nitro-L-arginine methyl ester(L-NAME), dose dependently, significantly inhibited the formation of $NO_2^-$ and $NO_3^-$ in cells stimulated with LPS, IFN-$\gamma$ and $H_2O_2$ at constant level(p<0.05). Catalase significantly inhibited the $H_2O_2$-induced augmentation of cytokine-induced $NO_2^-$ and $NO_3^-$ formation(p<0.05). But, boiled catalase did not produce a significant inhibition in comparison with the native enzyme. Another antioxidant 2-mercaptoethanol and orthophenanthroline dose-dependently suppressed $NO_2^-$ and $NO_3^-$ synthesis(p<0.05). Northern blotting demonstrated that H:02 synergistically stimulated the cytokine-induced iNOS mRNA expression in RA W264.7. Conclusion: These results suggest that $H_2O_2$ contributes to inflammatory process by augmenting the iNOS expression and nitric oxide synthesis induced by cytokines.

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Synthesis and Characterization of Polybenzimidazoles Containing Perfluorocyclobutane Groups for High-temperature Fuel Cell Applications

  • Chang, Bong-Jun;Kim, Dong-Jin;Kim, Jeong-Hoon;Lee, Soo-Bok;Joo, Hyeok-Jong
    • Korean Membrane Journal
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    • v.9 no.1
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    • pp.43-51
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    • 2007
  • This paper describes the preparation and characterization of two kinds of fluorinated polybenzimidazole (PBI)s which can be potentially used for phosphoric acid-doped, high-temperature polymer electrolyte membrane fuel cells. Two kinds of perfluorocyclobutane (PFCB)-containing monomers were prepared via following synthetic steps; after fluoroalkylation of methyl 3-(hydroxy) benzoate and methyl 4-(hydroxy) benzoate with 1,2-dibromotetrafluoroethane and subsequent Zn-mediated dehalogenation, these compounds were cyclodimerized at $200^{\circ}C$ affording the ester-terminated monomers containing PFCB ether groups. The synthesized intermediates and monomers were characterized using FT-IR, $^1H-NMR,\;^{19}F-NMR$, and mass spectroscopy. The fluorinated PBIs were then successfully prepared through the solution polycondensation of the monomers and 3,3'-diaminobenzidine in polyphosphoric acid. Compared with traditional PBI, the glass transition temperatures of the fluorinated PBIs were obtained at $262^{\circ}C\;and\;269^{\circ}C$ which are lower than that of PBI and their initial degradation temperatures were still high over $400^{\circ}C$ under nitrogen. The fluorinated PBIs showed higher d-spacing values and improved solubility in several organic solvents as well as phosphoric acid, which confirmed they could be good candidates for the high temperature fuel cell membranes.

Synthesis and Evaluation of Ecofriendly Nontoxic Cleaning Agents (무독성 친환경 세정제의 합성 및 평가에 관한 연구)

  • Kim, Jong Cheon;Ryu, Young;Hong, Yeon Heui;Kim, Seok Chan
    • Applied Chemistry for Engineering
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    • v.25 no.5
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    • pp.548-551
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    • 2014
  • In order to reduce toxicity on the human body, four new cleaning agents (1-4) containing ester and ether functionalities have been invented. The synthesized cleaning agents's physical properties, biodegradabilities, and $LD_{50}$ values, which were conducted by Korea Testing Certification Institute by using standard method, showed excellent values. A specimen for cleaning ability was prepared by cutting in $60{\times}40mm$ size of stainless steel plate. The surface of the above specimens was treated with four different kinds of contaminants, such as cutting oil, anti-rust oil, drawing oil, and lubricating oil. Contaminated specimens were then immersed in compounds (1-4) for 1 to 5 minutes to dissolve oil in the cleaning agent. The data indicate that all compounds (1-4) exhibit good cleaning ability toward four contaminant oils. It is also confirmed that these compounds can be applicable to various industrial cleaning fields as nontoxic and biodegradable cleaning agents because of their excellent biodegradabilities and $LD_{50}$ values.

Effects of BanhabackchulChunma-tang on the Vascular Relaxation and its mechanism (혈관 긴장성 조절에 미치는 반하백출천마탕)

  • Kim Yon Tae;Chae Jong Koo;Kim Gil Whon;Shin Heung Mook
    • Journal of Physiology & Pathology in Korean Medicine
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    • v.16 no.1
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    • pp.62-66
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    • 2002
  • Hypertension is not only a well-established cardiovascular risk factor but also increase the risk of atherosclerosis. Most studies conducted to investigate the effectiveness of treatment for cardiovascular disease such as hypertension have focused primarily on conventional drug and physiotherapeutic treatments. BanhabackchulChunma-tang(半夏白朮天麻湯:BCT) is popular herbal medicine used in clinic for the treatment of various symptoms of drulatory disorders and weakness of digestive system, including anorexa and nausea with vertigo, severe headache, vomiting and so on. However, the mechanisms underlying its efficacy are unknown. This study investigated the effects of BCT as an alternative medication on the contraction induced by phenylephrine and KCI in rat thoratic aorta. BCT revealed siginificant relaxation on phenylephrine-induced arterial contraction, but revealed noncompetitive effect on concentration responses of phenylephrine-induced contraction. Treatment of N-L/sup ω/ -argine methyl ester(L-NAME) and methylene blue(MB)(10/sup -5/M) reduced the relaxation of BCT. BCT also increased in vitro NO production. It suggest that the relaxation effect of BBT is related with NO pathway, becausse the effect of L-NAME and MB are due to inhibition of NO synthesis from endothelial cells. These results indicate that BCT would be effective in hypertension treatment and its mechanism of relaxtion on arterial contraction is likely to be related with NO production, blocking of α-receptor and signal transduction after receptor activation.