Synthesis of the o-quinones and other oxidized metabolites of polycyclic aromatic hydrocarbons implicated in carcinogenesis.
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.
Harvey
Ronald G
RG
The Ben May Institute for Cancer Research, University of Chicago, Chicago, IL 60637, USA. rharvey@ben-may.bsd.uchicago.edu
Dai
Qing
Q
Ran
Chongzhao
C
Penning
Trevor M
TM
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
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