• Title/Summary/Keyword: $C_8$-N bond cleavage

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

  • Kim, Sin-Kyu;Kim, Dong-Hyun;Chung, Kyung-Hee;Hwang, Soon-Ho;Kim, Jae-Hyun
    • YAKHAK HOEJI
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    • v.38 no.1
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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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Studies on the Synthesis of Protoberberine Related Compounds and its Activities (프로트베르베린 관련화합물 합성 및 활성검토)

  • 황순호;임형엽;우성주;김재현;김동현;김신규
    • YAKHAK HOEJI
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    • v.39 no.1
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    • pp.36-40
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    • 1995
  • In order to investigate the biological activity of protoberberine derivatives, they were synthesized four derivatives (1-4) of 7,8 adduct of cycloberberine, two derivatives (5, 6) treated with alkylamine or phenylamine, four compounds (7, 8) and (9, 10) adduct with 1,3-dichloroacetone and oxalychloride. Antibacterial activity of these synthesized compounds was tested.

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Synthesis of Protoberberine Derivatives and Studies on Their Biological Activities (Protoberberine 유도체합성 및 활성연구)

  • Lee, Ma-Sae;Chung, Sung-Hyun;Kim, Dong-Hyun;Choung, Se-Young;Kim, Sin-Kyu
    • YAKHAK HOEJI
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    • v.34 no.5
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    • pp.296-301
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    • 1990
  • Irradiation of the berberinephenolbetaine in a stream of argon produced the 8,14-cycloberberines [1]. On treatment with ethylchloroformate $C_8-N$ bond cleavage of the compound [1] occurred, accompanied with dehydrochlorination to give 7-ethylcarboxyisoquinoline [3], and the product [3] treated with strong alkali solution to give the 13-oxonorotensane [4] in 64% yield. Irradiation of the compound [4] converted easily to dihydro-8H-dibenzo[a, g] quinolizine-8-one [5]. and then the compound [5] was treated with methyliodide to give the 8-oxo-quinolizinium methiode. The intermediate colume chromatography on IRA-400 afforded the benzo[c, g]azecine-5-one[6] in 63% yield. The results of biological activities for these compounds are also presented.

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