• 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.

• 약학회지
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• 제38권4호
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• pp.451-454
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• 1994

In accordance with reported references, 8-methyl-8,14-cycloberbine was derived from berberinephenolbetaine. On acidic treatment the 8-methyl-8,14-cycloberbines were converted easily to the compounds $1{\sim}7$ in good yields. We developed a novel method for a synthesis of the C8-N bond adduct compounds 8 and 9 from 8-methyl-8,14-cycloberbine by treatment with oxalyl chloride, and 1,3-dichloroaceton.

• 약학회지
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• 제34권5호
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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.

• 약학회지
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• 제40권5호
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• pp.487-490
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• 1996

The 13-hydroxyberbine(1), derived from berberinephenolbetaine, has been derivatized to furnish a variety of compounds such as 13-oxoberbine(2), 13-thioberbine(3), 13-chloroberbi ne(4), 13-(2-methylaziridine)berbine(5) and 13-carbolactoneberbine(6). Antitumor activity of these compounds was tested.

• 약학회지
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• 제36권1호
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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.