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Protoberberine의 고급지방산 유도체합성 및 활성연구(V)
김신규(Sin Kyu Kim),권창호(Chang Ho Kwon),육창수(Chang Soo Yook),노영수(Young Soo Rho),서성훈(Seong Hoon Seo),정세영(Se Young Choung),정성현(Sung Hyun Chung),김동현(Dong Hyun Kim),황순호(Soon Ho Hwang) 대한약학회 1992 약학회지 Vol.36 No.1
Irradiation of phenolbetaine in a stream of nitrogen produced 8,14-cycioberbine[1]. Compound[1] was treated with 10% HCl solution to give the 8,14-cycioberbine[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-choloroethyl) amine. In the other synthetic pathway when compound[5] was treated with POCl3 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.
김신규(Sin Kyu Kim),이형원(Hyung Won Lee),김인종(In Jong Kim),이마세(Ma Se Lee) 대한약학회 1992 약학회지 Vol.36 No.3
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 C6-N bond cleavage followed by recyclization between C6 and C13 position of the protoberberine. Recently we have achieved the biomimetic transformation of protoberberine alkaloid, berberine into benzo[C]phenanthridine alkaloid, chelerythrine.
김신규(Sin Kyu Kim),김동현(Dong Hyun Kim),정경희(Kyung Hee Chung),황순호(Soon Ho Hwang),김재현(Jae Hyun Kim) 대한약학회 1994 약학회지 Vol.38 No.1
Irradiation of the berberinephenolbetaine [1] effected valence tautamerization to give 8,14-cycloberbine[2], 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 indroduced by the structural modification of berberinephenolbetaine.