A NEW STRATEGY FOR THE SYNTHESIS OF POLYCHLORINATED BIPHENYL METABOLITES

被引:50
作者
BAUER, U [1 ]
AMARO, AR [1 ]
ROBERTSON, LW [1 ]
机构
[1] UNIV KENTUCKY,GRAD CTR TOXICOL,LEXINGTON,KY 40506
关键词
D O I
10.1021/tx00043a012
中图分类号
R914 [药物化学];
学科分类号
100701 ;
摘要
A general and high-yielding synthetic route is presented by which a variety of chlorinated dihydroxybiphenyl metabolites may be synthesized. These synthetic standards will permit the investigation of novel pathways of polychlorinated biphenyl activation. The biphenyldiols were synthesized via palladium-catalyzed cross-coupling of dimethoxyphenylboronic acids with aryl bromides in the presence of a base. The formed dimethoxybiphenyls were demethylated using boron tribromide to yield the chlorinated dihydroxybiphenyls. These compounds were characterized by IR, NMR, and GC/MS.
引用
收藏
页码:92 / 95
页数:4
相关论文
共 29 条
[1]   INVITRO METABOLISM OF (C-14)4-CHLOROBIPHENYL AND (C-14)2,2',5,5'-TETRACHLOROBIPHENYL BY HEPATIC MICROSOMES FROM RATS AND PIGEONS - EVIDENCE AGAINST AN OBLIGATORY ARENE OXIDE IN AROMATIC HYDROXYLATION REACTIONS [J].
BORLAKOGLU, JT ;
HAEGELE, KD ;
REICH, HJ ;
DILS, RR ;
WILKINS, JPG .
INTERNATIONAL JOURNAL OF BIOCHEMISTRY, 1991, 23 (12) :1427-1437
[2]   METABOLISM OF DICHLOROBIPHENYL, TRICHLOROBIPHENYL, TETRACHLOROBIPHENYL, PENTACHLOROBIPHENYL AND HEXACHLOROBIPHENYL BY HEPATIC MICROSOMES ISOLATED FROM CONTROL ANIMALS AND ANIMALS TREATED WITH AROCLOR-1254, A COMMERCIAL MIXTURE OF POLYCHLORINATED-BIPHENYLS (PCBS) [J].
BORLAKOGLU, JT ;
WILKINS, JPG .
COMPARATIVE BIOCHEMISTRY AND PHYSIOLOGY C-TOXICOLOGY & PHARMACOLOGY, 1993, 105 (01) :95-106
[3]   REDOX AND ADDITION CHEMISTRY OF QUINOID COMPOUNDS AND ITS BIOLOGICAL IMPLICATIONS [J].
BRUNMARK, A ;
CADENAS, E .
FREE RADICAL BIOLOGY AND MEDICINE, 1989, 7 (04) :435-477
[4]  
CORRIU RJP, 1972, J CHEM SOC CHEM COMM, P144
[5]  
GOTO M, 1974, CHEMOSPHERE, V5, P227
[6]  
GOTO M, 1975, CHEMOSPHERE, V3, P177
[7]   TISSUE DISTRIBUTION OF PCB COMPONENTS IN SWINE AND SHEEP FED 3 DIFFERENT RATIONS CONTAINING AROCLORS 1242 AND 1254 [J].
HANSEN, LG ;
WELBORN, ME ;
BORCHARD, RE ;
TESKE, RH ;
METCALF, RL .
ARCHIVES OF ENVIRONMENTAL CONTAMINATION AND TOXICOLOGY, 1977, 5 (03) :257-278
[8]   METABOLISM OF DICHLOROBIPHENYLS BY HIGHLY PURIFIED ISOZYMES OF RAT-LIVER CYTOCHROME-P-450 [J].
KAMINSKY, LS ;
KENNEDY, MW ;
ADAMS, SM ;
GUENGERICH, FP .
BIOCHEMISTRY, 1981, 20 (26) :7379-7384
[9]   METABOLISM OF DICHLOROBIPHENYLS BY HEPATIC-MICROSOMAL CYTOCHROME-P-450 [J].
KENNEDY, MW ;
CARPENTIER, NK ;
DYMERSKI, PP ;
KAMINSKY, LS .
BIOCHEMICAL PHARMACOLOGY, 1981, 30 (06) :577-588
[10]   METABOLISM OF MONOCHLOROBIPHENYLS BY HEPATIC-MICROSOMAL CYTOCHROME-P-450 [J].
KENNEDY, MW ;
CARPENTIER, NK ;
DYMERSKI, PP ;
ADAMS, SM ;
KAMINSKY, LS .
BIOCHEMICAL PHARMACOLOGY, 1980, 29 (05) :727-736