Synthesis of Suspected Carcinogenic Metabolites of 7 H-Benzo [c] fluorene, a Coal Tar Component Implicated in Causation of Lung Tumors

JQ Wang, EH Weyand, RG Harvey

Index: Wang, Ji-Quan; Weyand, Eric H; Harvey, Ronald G The Journal of organic chemistry, 2002 , vol. 67, # 17 p. 6216 - 6219

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Citation Number: 15

Abstract

High incidences of lung tumors were observed in mice fed coal tar in their diet. The principal component of tar that gives rise to DNA-bound adducts in mouse lung was identified as 7 H- benzo [c] fluorene (B c F). We now report the synthesis of suspected active metabolites of B c F, specifically the trans-3, 4-dihydrodiol of B c F (2), its likely proximate carcinogenic metabolite, and the corresponding anti-and syn-diol epoxides of B c F (3 and 4) in which ...