• 제목/요약/키워드: Regioselective

검색결과 145건 처리시간 0.026초

프로토베르베린 관련 화합물합성 및 항균작용 (Synthesis of Protoberberine Related Compounds and Their Antifungal Activities)

  • 김신규;김동현;정경희;황순호;김재현
    • 약학회지
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    • 제38권1호
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    • pp.91-96
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    • 1994
  • Irradiation of the berberinephenolbetaine [1] effected valence tautamerization to five 8,14-cycloberbine[21, which was converted to the spirobenzylisoquinolines by regioselective C-N bond cleavage A variety of ring systems such as compounds [4], [5] and [6] were introduced by the structural modification of berberinephenolbetaine.

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Photochemistry of 1-(o-substituted -phenyl)-2-pentamethyldishilanyl Ethynes

  • Shim, Sang-Chul;Park, Seung-Ki
    • Journal of Photoscience
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    • 제6권1호
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    • pp.13-19
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    • 1999
  • Irradiation of 1-(o-allyloxyphenyl)-2-pentamethyldisilanylenthyne 2a in methanol yields two 1 : 1 photoaddition products 3 and 4 via silacyclopropene intermediate. Photolysis of 2a with acetone in deaerated methylene chloride yields site specific and regioselective 1 : 1 adducts 6 ad 7 via silacyclopropene and 1-sila-1, 2-propdiene intermediate, respectively. Photolysis of 2a and 1-(o-(3', 3'-dimethyl-2'-propenylox)phenyl)-2-pen-tamethyldisilanylethyone 2b in benzene provides novel stereoselevtive intramolecular cyclization products 10 and 11, respectively. Irradiation of 1-(o-acetoxyphenyl)-2-pentamethyldisilanyl ethyne 2c in benzene yields the photo-Fries rearrangement products 18 and 19 and a photoproduct 17 via silacyclopropene intermediate. Photolysis of 1-(o-methoxycarbonlymethoxyphenyl)-2-pentamethyl disilanylenthyne 2d in benzene provides a novel intramolecular cycloaddition product 25 and 1-(o-methoxycarbonylemthoxiyphenyl)-2-trimethylsilylethyne 26 via silacyclopropene intermediate.

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Solubility Enhancement of Flavonoids by Cyclosophoraose Isolated from Rhizobium meliloti 2011

  • Kang Si-Mook;Lee Sang-Hoo;Kwon Chan-Ho;Jung Seun-Ho
    • Journal of Microbiology and Biotechnology
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    • 제16권5호
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    • pp.791-794
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    • 2006
  • Cyclosophoraose (cyclic $\beta-(1,2)-glucan$, Cys) isolated from Rhizobium meliloti, a soil microorganism, was used as a solubility enhancer for flavonoids. The complexes of the cyclic oligosaccharide with flavonoids were confirmed through $^1H$ nuclear magnetic resonance (NMR) spectroscopic analysis. Flavonoids solubilized by Cys were quantitatively analyzed through high-performance liquid chromatography (HPLC). Among the flavonoids tested, the solubility of naringenin was greatly enhanced by Cys, compared with other compounds. The solubility of naringenin was enhanced about 7.1-fold by adding 10 mM Cys, compared with a control. $^1H$ NMR spectroscopic analysis indicated that the H-6 and H-8 protons, which are located on the A ring of naringenin, were greatly shifted upfield upon the complexation with Cys. This result suggested that Cys showed a regioselective interaction with the naringenin molecule upon the complexation, resulting in the solubility enhancement of naringenin.

Racemic Synthesis of Novel 6'-Methylene-5'-norcarbocyclic Purine Phosphonic Acid Analogues via Mitsunobu Reaction

  • Kim, Eun-Ae;Liu, Lian Jin;Hong, Joon-Hee
    • Bulletin of the Korean Chemical Society
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    • 제32권8호
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    • pp.2689-2694
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    • 2011
  • Novel 5'-norcarbocyclic adenine and guanine phosphonic acid analogues with 6'-electronegative moiety such as unsaturated C-C bond were designed and synthesized from commercially available 2-methylene-propane-1,3-diol (4). Regioselective Mitsunobu reaction successfully proceeded from an allylic functional group (${\pm}$)-12b at low reaction temperature in polar cosolvent (DMF/1,4-dioxane) to give purine phosphonate analogues (${\pm}$)-13 and (${\pm}$)-20. The purine nucleoside phosphonate and phosphonic acid analogues were subjected to antiviral screening against HIV-1. Guanine analogue (${\pm}$)-23 shows significant anti-HIV activity in PBM cell lines ($EC_{50}=8.1\;{\mu}M$).

A Concise Synthesis of (-)-Cytoxazone via Regioselective and Stereoselective Introduction of Amino Group using Chlorosulfonyl Isocyanate

  • Kim, Ji-Duck;Jung, Young-Hoon
    • 한국응용약물학회:학술대회논문집
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    • 한국응용약물학회 2003년도 Annual Meeting of KSAP : International Symposium on Pharmaceutical and Biomedical Sciences on Obesity
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    • pp.116-116
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    • 2003
  • In 1998, Osada and co-workers isolated 140 mg of a novel cytokine modulator from 18 L of the culture broth of Streptomyces RK95- 31 isolated from a soil sample in Hiroshima Prefecture. This new immunosuppressant was named (-)-cytoxazone and its absolute configuration was determined on the basis of its NMR, CD and X -ray analysis. It interferes with cytokine IL4, IL10 and IgG production by selective inhibition of the signaling pathway of Th2 cells, but not Thl cells. Inhibitors of Th2-dependent cytokine production have potential as potent chemotherapeutic agents in the field of immunotherapy. The (-)-cytoxazone is different from known immunomodulators such as FK 506 and rapamycin in respect of structure and biological activity. As such cytoxazone should be a useful tool for understanding signaling pathways in Th2 cells, the synthesis of (-)-cytoxazone is of interest for the development of new cytokine modulators.

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Fast, Efficient and Regioselective Conversion of Epoxides to β-Hydroxy Thiocyanates with NH4SCN/Zeolite Molecular Sieve 4 Å under Solvent-Free Conditions

  • Eisavi, Ronak;Zeynizadeh, Behzad;Baradarani, Mohammad Mehdi
    • Bulletin of the Korean Chemical Society
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    • 제32권2호
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    • pp.630-634
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    • 2011
  • Solvent-free conversion of various epoxides to their corresponding $\beta$-hydroxy thiocyanates was carried out successfully with $NH_4SCN$/zeolite molecular sieve $4{\AA}$ system at room temperature. The reactions were completed within 2 - 7 min to give thiocyanohydrins with perfect regioselectivity and isolated yields. Moreover, the zeolite can be reused for several times without losing its activity.

벤조펜안드리딘과 관련된 알칼로이드의 합성 (Synthesis of Benzophenanthridine-Related Alkaloids)

  • 김신규;이형원;김인종;이마세
    • 약학회지
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    • 제36권3호
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    • pp.250-254
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    • 1992
  • Benzo[C]phenanthidine alkaloids were found to exhibit considerably strong antileukemic activies. These alkaloids have been shown to be biosynthesized from the corresponding alkaloids throung an oxidative $C_6-N$ bond cleavage followed by recyclization between $C_6\;and\;C_{13}$ position of the protoberberine. Recently we have achieved the biomimetic transformation of protoberberine alkaloid, berberine into benzo[C]phenanthridine alkaloid, chelerythrine.

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3-Aryltetrahydro-1,2-benzisoxazolin-4-one 유도체의 합성 및 제초 활성 (Synthesis and herbicidal activity of 3-aryltetrahydro-1,2-benzisoxazolin-4-one derivatives)

  • 김형래;송종환;전동주;홍경식;유응걸
    • 농약과학회지
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    • 제2권1호
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    • pp.104-106
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    • 1998
  • 3-Aryltetrahydro-1,2-benzisoxazolin-4-one derivatives were prepared by regioselective 1,3-dipolar cycloaddition reactions of various aryl nitrile oxides with 2-cyclohexen-1-one. The structures of these compounds were designed as a modifications of triketone herbicides and showed good herbicidal activity.

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Regioselective Nitration of Inactive 4,4-Dibromobiphenyl with Nitrogen Dioxide and Molecular Oxygen over Zeolites: An Efficient Preparation of 4,4'-Dibromo-2-nitrobiphenyl

  • Wang, Wei;Peng, Xinhua;Chen, Nan
    • 대한화학회지
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    • 제58권1호
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    • pp.72-75
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    • 2014
  • In the presence of zeolites, 4,4'-dibromobiphenyl could be region-selectively nitrated by the action of nitrogen dioxide and molecular oxygen. The ratio of 4,4'-dibromo-2-nitrobiphenyl to 4,4'-dibromo-3-nitrobiphenyl could reach 14 in a high yield of 90%. Zeolites could be easily regenerated by heating and reused four times to give the results similar to those obtained with fresh catalyst. Compared with the classic nitration method, no nitric acid and sulfuric acid were used, which suggested that the method was an environmentally economic process.

Solvent-free 조건하에서 H3PMo12O40 촉매에 의한 Z-Aldoximes의 (Regioselective Synthesis of Z-Aldoximes Catalyzed By H3PMo12O40 under Solvent-Free Conditions)

  • Eshghi, Hossein;Alizadeh, Mohammad Hasan;Davamdar, Ehsan
    • 대한화학회지
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    • 제52권1호
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    • pp.52-56
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    • 2008
  • 제법을 위한 쉽고 효과적인 이 방법은 solvent-free하에서 H3PMo12O40 촉매를 사용해서 개선되었다. 이 방법의 큰 이점은 조작의 간편성, 더 작은 촉매량, 선택성, 온화한 반응조건,짧은 반응 시간 그리고 높은 수율이다. 재생된 촉매는 어떤 정제도 없이 다시 사용되어질 수 있다.