• 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.

• 약학회지
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• 제38권4호
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• pp.455-461
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• 1994

Each nitrogen and oxygen site isotope enriched the cyclophosphamide metabolite phosphoramide mustard was synthesized. Reaction of N,N-bis(2-chloroethyl)phosphoramidic dichloride$[Cl_2P(O)N(CH_2CH_2Cl)_2]$ with benzyl alcohol and ammonia gave N,N-bis(2-chloroethyl)phosphorodiamidic acid phenylmethyl ester $[BzO(H_2N)P(O)N(CH_2CH_2Cl)_2]$. Catalytic hydrogenation of this benzyl ester followed by the addition of cyclohexylamine provided PM. Incorporation of $^{15}NH_3$ into this general scheme gave PM with a $^{15}NH_2$ moiety. Glycine-$^{15}N$ was converted to bis(2-chloroethyl)amine-$^{15}N$ hydrochloride which, in turn, provided for N,N-bis(2-chloroethyl)phosphorodiamidic-$^{15}N$ dichloride. Use of this compound in the general synthetic pathway yielded PM CHA with $^{15}N$ in the mustard moiety. $^{17}O$-Enriched PM was generated through the use of benzyl alcohol-$^{17}O$. To obtain the alcohol, labelled benzaldehyde was made by exchange with $^{17}OH_2$ and was then reduced with sodium borohydride.

• 한국미생물생명공학회:학술대회논문집
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• 한국미생물생명공학회 1975년도 추계학술발표회
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• pp.179.2-180
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• 1975

자외선, $methyl-bis(\beta-chloroethyl)$ amine 등과같은 물리적 및 화학적인 mutagenic agents를 처리함으로써 페니실린을 생산하는 많은 mutants를 분리하고 그 균주들의 페니실린 생산율을 측정하여 우수한 페니실린 생산균주의 개발을 위한 연구가 진행되었다.(중략)

• 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.