• Title/Summary/Keyword: Isoxazoline

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Single Organic Molecules Designed as Nanoscale Connectors: Fullerene Isoxazoline Derivatives

  • Lee, Han-Myong;Lee, Chang-Hoon;Cho, Min-Sil;Hwang, Yong-Gyoo;Lee, Kee-Hag
    • Bulletin of the Korean Chemical Society
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    • v.25 no.12
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    • pp.1850-1854
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    • 2004
  • Recently a fullerene isoxazoline was reported as an example for nanoscale connectors in molecular electronic devices. The construction of nanoscale devices is a potentially important area of technology. By using the semiempirical PM3 calculation, we optimized the structures for two fullerene isoxazoline derivatives and thirteen regioisomers of the second addition of a nitride oxide to a fullerene isoxazoline derivative. Our results suggest that fullerene isoxazoline derivatives could be used as nanoscale connectors with the possibility of attaching of spacer units in a specific angle arrangement.

Synthesis and Herbicidal Activities of 5-benzyloxymethyl-3-(thiophen-4-yl)-1,2-isoxazoline derivatives (5-Benzyloxymethyl-3-(thiophen-4-yl)-1,2-isoxazoline 유도체의 합성과 제초활성)

  • Song, Jong-Hwan;Jeon, Dong-Ju
    • The Korean Journal of Pesticide Science
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    • v.12 no.2
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    • pp.197-200
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    • 2008
  • Novel series of 5-benzyloxymethyl-3-(thiophen-5-yl)-1,2-isoxazoline derivatives were designed and synthesized, and their herbicidal activities to diverse weeds were tested under flooded paddy conditions in a greenhouse. Among them, some compounds (3d-f) showed good activities to dominant weeds such as Echinocloa orizycola and Monochoria vaginalis presl. at a rate of 0.063 kg/ha without the serious injury toward rice.

Synthesis and Herbicidal Activities of 5-Benzyloxymethyl-3-(thiophen-5-yl)-1,2-isoxazoline and Their Related Derivatives (5-Benzyloxymethyl-3-(thiophen-5-yl)-1,2-isoxazoline 유도체의 합성과 제초활성)

  • Jeon, Dong-Ju;Song, Jong-Hwan;Kim, Hyoung-Rae;Kim, Eun-Ju;Hwang, In-Taek
    • The Korean Journal of Pesticide Science
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    • v.11 no.2
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    • pp.67-71
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    • 2007
  • Nobel series of 5-benzyloxymethyl-3-(thiophen-5-yl)-1,2-isoxazoline derivatives were designed and synthesized. The herbicidal activities of these compounds to main dominant weeds to these compounds were evaluated in pot tests that simulated rice paddy conditions. Most of the compounds showed high herbicidal activity to main dominant weeds occurring in rice field without the serious rice injury.

Synthesis of Perfluorinated Heterocyclic Compounds Having a Long Alkyl Chain Functionality by 1,3-Dipolar Cycloaddition

  • Lee, Chan-Woo;Hwang, Ho-Yun;Park, Joo-Yuen;Chi, Ki-Whan
    • Bulletin of the Korean Chemical Society
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    • v.31 no.5
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    • pp.1305-1308
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    • 2010
  • Regioselective perfluorinated isoxazolidine (5 and 7), isoxazoline (9) and 1,2-addition products (6 and 8) having a long alkyl chain functionality have been prepared by 1,3-dipolar cycloaddition between a 1,3-dipole (NH-nitrone or nitrile oxide) and dipolarophile (perfluoro-2-methyl-2-pentene or styrene), respectively. Interestingly, unusual extended conjugated form of isoxazoline adduct (10) was obtained by dehydrofluorinated reaction from the corresponding perfluorinated isoxazoline adduct (9) which was derived from cycloadition between the perfluorinated long alkyl nitrile oxide 1,3-diplole and styrene olefin. This synthetic methodology of heterocyclic compound having a long alkyl chain functionality is useful for the designing of synthetic strategy and potential self-assembled monolayers (SAM) application. These derivatives were characterized by IR, $^1H$ and $^{19}F$ NMR, and MASS analysis.

Inhibition of HIV-1 Pretense by Novel Dipeptide Isosteres Containing 2-Isoxazoline or $\alpha$-Hydroxy Ketomethylene

  • Kim, Do-Hyung;Park, Kwan-Yong;Chung, Yong-Jun;Kim, Byeang-Hyean
    • Biomolecules & Therapeutics
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    • v.2 no.2
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    • pp.155-160
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    • 1994
  • Human immunodeficiency virus type 1 (HIV-1) protease is essential for the replication of the virus and it is therefore an attractive target for antiviral drugs of HIV-1. Several dipeptide isosteres containing 2-isoxazoline or $\alpha$-hydroxy ketomethylene have been synthesized and their inhibitory effects on the HIV-1 protease examined. The enzymatically active HIV-1 protease was purified to homogeniety from E. coli transformed with a recombinant plasmid (pMAL-pro) containing the entire gene encoding the protease. The purified protease had the substrate specificity with Km value of 9.8$\mu$M when an undecapeptide His-Lys-Ala-Arg-Val-Leu-(p-nitro)Phe-Glu-Ala-Nle-Ser-amide was used as a substrate, and the products from the substrate after specific cleavage by HIV-1 protease were analyzed by HPLC. The synthetic compounds containing dipeptide isosteres showed specific inhibitory effects while a dipeptide isostere containing an isoxazoline ring inhibited the HIV-1 protease competitively with Ki value of 500 $\mu$M. Even if the inhibition effects of HIV-1 protease were not very high, these novel dipeptide isosteres can be used as key structural moieties for developing specific inhibitors of HIV-1 protease.

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ACE 억제제를 위한 펩타이드 등입체성 분자 합성 연구

  • 김병현;류은정
    • Proceedings of the Korean Society of Applied Pharmacology
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    • 1993.04a
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    • pp.121-121
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    • 1993
  • Angiotensin Converting Enzyme (ACE)의 효과적인 억제제를 합성하기 위하여 ketomethylene dipeptide isoster와 2-isoxazoline dipeptide isoster를 얻는 방법을 확립하였다. 상기 등입체성 분자들은 아미노산으로부터 유도된 아미노 니트릴 옥사이드의 고리더함반응을 이용하여 효율적으로 합성하였다. 얻어진 이 화합물로부터 ACE 억제제 후보물질 (1, 2)의 합성이 연구되고 있다.

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Synthesis and Herbicidal Activity of New Hexahydrobenzisoxazole Derivatives (새로운 hexahydrobenzisoxazole derivatives 유도체의 합성 및 제초활성)

  • Kim, Hyoung-Rae;Park, Hyun-Ju;Kim, Hyung-Ki;Song, Jong-Hwan;Jeon, Dong-Ju;Kim, Kyung-Mahn;Kim, Tae-Joon;Ryu, Eung-K.
    • The Korean Journal of Pesticide Science
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    • v.3 no.3
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    • pp.68-70
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    • 1999
  • Hexahydro-1,2-bertzisoxazol-4-ols prepared from the diastereoselective reductions of 3-aryl-3a,4,5,6,7,7a-hexahydro-1,2-benzisoxazol-4-ones were reacted with benzyl chloride in the presence of sodium hydride to give new 4-benzyloxy-3a,4,5,6,7,7a-hexahydro-1,2-benzisoxazoles, which showed good herbicidal activity together with excellent selectivity on rice under submerged paddy conditions.

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