2,2',3,4',5,5',6-七塩素化ビフェニル(CBl87)の主代謝物の合成

概要

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Very recently, we have reported 2, 2', 3, 4', 5, 5', 6-heptachlorobiphenyl (heptaCB) (CB187)could be metabolized to two monohydroxy (0H)-metabolites and one dechlorinated OH metabolite by liver microsomes of rats, hamsters and guinea pigs. In this study, in order to determine the metabolic pathways of CB187, we tried to synthesize two OH-PCBs, namely4'-OH-2, 2', 3, 3', 5, 5', 6-heptaCB (CB178) and 3'-OH-CB187. After the diazo-coupling reaction with2, 3, 5, 6-tetrachloroaniline and 2, 3, 6-trichlorophenol as starting materials, the reaction mixture was applied to Silica gel 60 column chromatography. After the elution by n-hexane, the chloroform-eluate was pooled and applied to preparative HPLC. Two peaks containing two OH-PCBs (named as S-1 and S-2) were observed at the retention times of 20.54min and 20.49min in GC. Each fraction was methylated by dimethysulfate and recrystallized in methanol. As a result, the methylated derivative of S-1 and S-2 was obtained with 99.0% and 98.3% in purity and 3.2% (40mg) and 1.7% (21mg) in yield, respectively. From the data in GC/MS and ^1H-NMR, S-1 and S-2 were identified to be 4'-OH-CB178 and 3'-OH-CB187. Finally, a major metabolite of CB187 formed by animal liver microsomes was 4'-OH-CB178, whereas 3'-OH-CB187 was not found in animal.
中村学園大学の論文
2006-03-15