• Title/Summary/Keyword: Methyl acetate

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The Synthesis of $\alpha$-lhnctionalized Benzykmine ($\alpha$-Functionalized Benzylamine의 합성)

  • Kim, Hyeung-Jae;Cho, Su-Dong;Ahn, Chul Jin;Joo, Woo-Hong;Shin, Dong Soo
    • Journal of the Korean Chemical Society
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    • v.44 no.5
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    • pp.442-447
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    • 2000
  • $\alpha$-Functionalized benzylamine(Nu=OAc, OMe, N$_3$) will be very usefud as a starting material or synton in organic synthesis. We have investigated the first synthetic methodology of phthalimide-ben-zylacetate from benzylphthalimide, which are prepared in NBS/NaOAc/HOAc in chlorobenzene at 137$^{\circ}C$ for 12 hr in good yield. Finally, amino(phenyl)methyl acetate (1) was synthesized from phthalimide-benzyl acetate under NH$_2$NH$_2$/HOAC.

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Miscibility and Phase Separation Behavior of P(VDF-co-HFP) and Poly(vinyl methyl ketone) Blends (P(VDF-co-HFP)와 poly(vinyl methyl ketone) 블렌드물의 혼화성 및 상분리 거동)

  • 김영호;홍성돈;김갑진
    • Proceedings of the Korean Fiber Society Conference
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    • 2003.04a
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    • pp.319-320
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    • 2003
  • 압전성과 초전성을 나타내는 고분자인 poly(vinylidene fluoride)(PVDF)는 poly(methyl methacrylate), poly(vinyl acetate), 및 Poly(vinyl methyl ketone)(PVMK) 등과 블렌딩하면 혼화성(miscibility)이 있다. 이들 블렌드물들을 용융온도 이상으로 승온시키면 낮은 온도에서는 균일상으로 존재하지만, 온도가 계속 증가하면 상분리되어 LCST(lower critical solution temperature)를 나타낸다[1]. 이러한 승온에 의한 상분리 거동에서 외부전장을 가하면 전기활성 고분자인 PVDF에 영향을 주어 상분리 거동이 변화될 것으로 예산된다. (중략)

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Cytotoxic Phenylpropanoids from the Rhizomes of Alpinia galanga

  • NAM Joo-Won;KIM Sun-Jack;HAN Ah-Reum;LEE Sang Kook;SEO Eun-Kyoung
    • Biomolecules & Therapeutics
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    • v.13 no.4
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    • pp.263-266
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    • 2005
  • A bioassay-guided fractionation of the n-hexane and chloroform extracts of the rhizomes of Alpinia galanga led to the isolation of two active compounds, 1'S-1'-acetoxychavicol acetate (1) and p-coumaryl alcohol $\gamma$-O-methyl ether (2). 1'S-1'-acetoxychavicol acetate (1) exhibited significant cytotoxicity against all human cancer cell lines tested (A549; $IC_{50}$ 8.14, SNU 638; 1.27, HCTl16; 1.77, HT1080; 1.2, HL60; $IC_{50}$ 2.39 ${\mu}g/ml$), whereas p-coumaryl alcohol $\gamma$-O-methyl ether (2) showed selective cytotoxicity against the SNU638 cell ($IC_{50}$ = 1.62${\mu}g/ml$).

Studies on the Bis (amino-alkyl-oxo) Oxalate Derivatives As a Antidote of Lead poisoning (Bis (\beta$-amino-alkyl-oxo) oxalate 유도체의 납 중독 해독에 관한 연구)

  • 최선아;유미례;노영수;정성현;정세영
    • Environmental Analysis Health and Toxicology
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    • v.4 no.3_4
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    • pp.1-6
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    • 1989
  • The effects of his ($\beta$-amino-ethyl-oxo) oxalate and bis ($\alpha$-amino-methyl-oxo) oxalate on the toxicity of lead acetate in rast were examined. Rats were given intraperitoneally at the dose of lead acetate 45 mg/kg. The exposure of lead acetate showed the 70% decrease of ALAD ($\delta$-amino levulinic acid dehydratase) activity in red blood cell. In vivo 122 mg/kg administration of bis ($\beta$-amino-ethyl-oxo) oxalate and bis ($\alpha$-amino-methyl-oxo) oxalate showed the 50% increase of ALAD activity, whereas 149 mg/kg administeration of Ca-EDTA had no effect. In vitro, the same results were obtained. Both compounds had hemolytic activity at concentrations higher than that required for showing the 50% ALAD activity increase in vivo.

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Synthesis of 5-(p-Toluoyl)-1-Methylpyrrole-2-Acetic Acid [Tolmetin] (5-(p-톨루오일)-1-메틸피롤-2-아세트산의 합성)

  • Choi, Hong-Dae;Ma, Jung-Joo
    • YAKHAK HOEJI
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    • v.36 no.4
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    • pp.341-344
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    • 1992
  • A facile method for tolmetin, which is a potent antiinflammatory agent, is described. Friedel-Crafts reaction of 1-methylpyrrole with ethyl ${\alpha}-chloro-{\alpha}-(methylthio)acetate$ (1) gave ethyl ${\alpha}-methylthio$-1-methyl-2-pyrroleacetate (4), which was readily converted into ethyl 1-methyl-2-pyrroleacetate (5) by reductive desulfurization with zinc dust in acetic acid. Tolmetin was synthesized by Friedel-Crafts acylation of (5) with p-toluoyl chloride, followed by hydrolysis of the resultant ethyl 5-(p-toluoyl)-1-methylpyrrole-2-acetate (6).

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Effect of Different Biosynthetic Precursors on the Production of Nargenicin $A_1$ from Metabolically Engineered Nocardia sp. CS682

  • Koju, Dinesh;Maharjan, Sushila;Dhakal, Dipesh;Yoo, Jin Cheol;Sohng, Jae Kyung
    • Journal of Microbiology and Biotechnology
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    • v.22 no.8
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    • pp.1127-1132
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    • 2012
  • Nargenicin $A_1$ is a 28-membered polyketide macrolide, with antibacterial activity against methicillin-resistant Staphylococcus aureus, produced by Nocardia sp. CS682. In this study, the production of nargenicin $A_1$ was improved by enhancing the supply of different biosynthetic precursors. In Nocardia sp. CS682 (KCTC11297BP), this improvement was ~4.62-fold with the supplementation of 30 mM methyl oleate, 4.25-fold with supplementation of 15mM sodium propionate, and 2.81-fold with supplementation of 15 mM sodium acetate. In Nocardia sp. metK18 and Nocardia sp. CS682 expressing S-adenosylmethionine synthetase (MetK), the production of nargenicin $A_1$ was improved by ~5.57-fold by supplementation with 30 mM methyl oleate, 5.01-fold by supplementation with 15 mM sodium propionate, and 3.64-fold by supplementation with 15 mM sodium acetate. Furthermore, supplementing the culture broth of Nocardia sp. ACC18 and Nocardia sp. CS682 expressing the acetyl-CoA carboxylase complex (AccA2 and AccBE) with 30 mM methyl oleate, 15 mM sodium propionate, or 15 mM sodium acetate resulted in ~6.99-, 6.46-, and 5.58-fold increases, respectively, in nargenicin $A_1$ production. Our overall results showed that among the supplements, methyl oleate was the most effective precursor supporting the highest titers of nargenicin $A_1$ in Nocardia sp. CS682, Nocardia sp. metK18, and Nocardia sp. ACC18.

Synthesis of 2(3H)-Benzofuranone Derivatives from Substituted Phenols Using Methyl 2-chloro-2-(methylthio)acetate (메틸 2-클로로-2-(메틸티오)아세트산을 이용한 치환페놀류로부터 2(3H)-벤조푸란온 유도체의 합성)

  • Choi, Hong-Dae;Kim, Mi-Heun;Shin, Sang-Hoon;Son, Byung-Wha
    • YAKHAK HOEJI
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    • v.40 no.6
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    • pp.640-645
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    • 1996
  • 5-Alkyl-2(3H)-benzofuranones(3a-e) were prepared from Friedel-Crafts reaction of 4-alkylphenols with methyl 2-chloro-2-(methylthio)acetae(1) followed by the treatment of zinc du st-acetic acid. The reaction of disubstituted phenols with 1 in the presence of stannic chloride afforded 3-methyltWa-2(3H)-benzofuranone derivatives(11a-c), which were readily converted into 2(3H)-benzofuranone derivatives(12a-c) by desulfurization with zinc dust-acetic acid.

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Synthesis of 5-Aslkylthio (or sulfonyl) methyl-5-m-methoxy-phenylhydantion-3-acetic Acid Derivatives

  • Kwon, Soon-Kyoung;Park, Muoung-Suk;Nam, Young-Ju
    • Archives of Pharmacal Research
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    • v.16 no.4
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    • pp.322-326
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    • 1993
  • For the development of new antinflammatory and analgesic drugs, new 5-alkylthio (or sulfonyl) methyl-5-m-methoxyphenylhydantoin-3-acetic acid derivatives(alkyl; ethyl, propyl, butyl) were prepared. The 5,5 -disubstituted hydantoins which were used as starting materials, were prepared acording to Bucherer-Berg method. The reaction of ethyl chloroacelate with these compounds gave 3-acetate and the subsequent hydrolysis with dilute sodium hydroxide resulted in hydantoin 3-acetate and the subsequent hydrolysis with dilute sodium hydroxide resulted in hydantoin 3-acetic acid derivatives. Through the same procedure of equivalent hydroxide resulted in hydantoin 3-acetic acid derivatives. Through the same procedure of equivelent hydantions or the oxidation of 5-alkylthiohydantoin ocmpounds described above, 5-alkylsulfonylme-thyl-5-m-methoxyphenylhydantoin-30acetic acid derivatives were also synthesized.

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Synthesis of 2-Aryl-5-benzoxazolepropionic Acid Derivatives as Antiinflammatory Agent (항염증제로서 2-아릴-5-벤즈옥사졸프로피온산 유도체의 합성)

  • Choi, Hong-Dae;Kowak, Yong-Sil;Geum, Dek-Hyun;Son, Byeng-Wha
    • YAKHAK HOEJI
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    • v.38 no.5
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    • pp.504-510
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    • 1994
  • A facile synthesis of 2-aryl-5-benzoxazolepropionic acid derivatives(1 0a-d), which are potent antiinflammatory agent, is reported. Methyl ${\alpha}$-(p-hydroxyphenyl)propionate(5) was prepared from Friedel-Crafts reaction of isopropoxy benzene with methyl ${\alpha}$-chloro-${\alpha}$-(methylthio) acetate(1), followed by desulfurization, methylation and clevage of ether bond. Compounds(10a-d) were made from(5) by a sequence of nitration, reduction, formation of benzoxazole ring, and hydrolysis in good yields, respectively.

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An Improved Synthesis of Methyl p-Hydroxyphenylalkanoates

  • Choi, Hong-Dae;Kowak, Yong-Sil;Geum, Dak-Hyun;Son, Byeng-Wha
    • Archives of Pharmacal Research
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    • v.17 no.3
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    • pp.190-193
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    • 1994
  • Friedel-Crafts reaction isopropoxybenzene with methyl $\alpha$-chloro-$\alpha$-(maethylthio)acetate 1 afforded methyl $\alpha$-methylthio-p-isopropoxyphenylacetate 2d, which was readily converted into methyl p-isopropoxyphenylacetate 3 by reductive desulfurization with zinc dust in acetic acid. Methylation of 3 with sodium hydride and methyl iodide gave methyl $\alpha$-(p-isopropoxyphenyl)propionate 5. Methyl p-hydroxyphenylakanoates (4,6), useful intermediates for some medicines, were easily prepared by treatment of 3 and 5 with titanium tetrachloride, respectively.

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