• Title/Summary/Keyword: Regioselective ring-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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Synthesis of Benzophenanthridine-Related Alkaloids (벤조펜안드리딘과 관련된 알칼로이드의 합성)

  • Kim, Sin-Kyu;Lee, Hyung-Won;Kim, In-Jong;Lee, Ma-Se
    • YAKHAK HOEJI
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    • v.36 no.3
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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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Synthesis of Protoberberine Derivatives and Their Biological Activities (Protoberberine의 고급지방산 유도체합성 및 활성연구(V))

  • Kim, Sin-Kyu;Kwon, Chang-Ho;Yook, Chang-Soo;Rho, Young-Soo;Seo, Seong-Hoon;Choung, Se-Young;Chung, Sung-Hyun;Kim, Dong-Hyun;Hwang, Soon-Ho
    • YAKHAK HOEJI
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    • v.36 no.1
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    • pp.1-6
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    • 1992
  • Irradiation of phenolbetaine in a stream of nitrogen produced 8,14-cycioberbine[1]. Compound[1] was treated with 10% HCl solution to give the 8-hydroxycycloberbine[2] in 67.7% yield. Subsequently addition of ethylchloroformate to the compound[2] gave rise to the 8-hydroxy-7-ethylcarboxy-9, 10-dimethoxy-2, 3-methylenelioxy-13-oxo-norochotensane[3] in 78% yield. Treatment of the compound[3] with bis-(2-chloroethyl)amine then lead to the 7-bis(2-chloroethyl)carbamyl-norochoteneare[4]. On the other hand the compound[5], which is the 8-methoxynorochotensane, was derived when compound[1] was treated with methanol in a few drops of BF. Treatment of the compound[6], and the compound[7], 7-bis(2-chloroethyl)-carbanyl-8-methoxy-norocheyensane, was then synthesized by reaction of the compound[6] with bis(2-chloroethyl) amine. In the other synthetic pathway when compound[5] was treated with $POCl_3$ in dried benzene, 13-chloro-6-ene-norochetensane[8] with 42% yield was formed. Finally the 13-bis-(2-chloroethyl) amino-8-methoxy-norochotensane[9] was produced when we treated the compound[8] with bis-(2-chloroethyl) amine. In another pathway, reaction between phenolbetaine which is the precursor of the compound[1] and benzoylchloride in dried chloroform gave us the 5,6,7 trihydro-2, 3-methylene-dioxy-9-chloromethyl-10, 11-dimethoxyphenylisoquinoline-8-benzoate[10] in 73% yield. The results of biological activities for these compounds are also presented in Table I and II.

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