title: Synthesis of the o-quinones and other oxidized metabolites of polycyclic aromatic hydrocarbons implicated in carcinogenesis.
abstract: Efficient new syntheses of the o-quinone derivatives of benzo[a]pyrene (BPQ), 7,12-dimethylbenz[a]anthracene (DMBAQ), and benz[a]anthracene (BAQ), implicated as active carcinogenic metabolites of the parent polycyclic aromatic hydrocarbons (PAHs), are reported. These PAH quinones also serve as starting compounds for the synthesis of the other active metabolites of these PAHs thought to be involved in their mechanism(s) of carcinogenesis. The latter include the corresponding o-catechols, trans-dihydrodiols, and the corresponding anti- and syn-diol epoxides.
authors.affiliation: The Ben May Institute for Cancer Research, University of Chicago, Chicago, IL 60637, USA. rharvey@ben-may.bsd.uchicago.edu
authors.forename: Ronald G
authors.initials: RG
authors.lastname: Harvey
authors.forename: Qing
authors.initials: Q
authors.lastname: Dai
authors.forename: Chongzhao
authors.initials: C
authors.lastname: Ran
authors.forename: Trevor M
authors.initials: TM
authors.lastname: Penning
mesh_terms: D015127:9,10-Dimethyl-1,2-benzanthracene / Q000737:chemistry; D001551:Benz(a)Anthracenes / Q000737:chemistry; D001564:Benzo(a)pyrene / Q000737:chemistry; D002273:Carcinogens / Q000138:chemical synthesis* / Q000378:metabolism; D002396:Catechols / Q000737:chemistry; D004852:Epoxy Compounds / Q000737:chemistry; D015394:Molecular Structure; D010084:Oxidation-Reduction; D011084:Polycyclic Aromatic Hydrocarbons / Q000138:chemical synthesis*; D011809:Quinones / Q000138:chemical synthesis*; D013237:Stereoisomerism
chemical_list: D001551:Benz(a)Anthracenes; D002273:Carcinogens; D002396:Catechols; D004852:Epoxy Compounds; D011084:Polycyclic Aromatic Hydrocarbons; D011809:Quinones; D001564:Benzo(a)pyrene; D015127:9,10-Dimethyl-1,2-benzanthracene; C030935:benz(a)anthracene