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: Ronald G Harvey, Qing Dai, Chongzhao Ran, Trevor M Penning
• Journal: The Journal of organic chemistry (J Org Chem) Vol. 69 Issue 6 Pg. 2024-32 (Mar 19 2004) ISSN: 0022-3263 [Print] United States
• PMID: 15058949 (Publication Type: Comparative Study, Journal Article, Research Support, U.S. Gov't, P.H.S.)

Chemical References

• Benz(a)Anthracenes
• Carcinogens
• Catechols
• Epoxy Compounds
• Polycyclic Aromatic Hydrocarbons
• Quinones
• Benzo(a)pyrene
• 9,10-Dimethyl-1,2-benzanthracene
• benz(a)anthracene

Topics

• 9,10-Dimethyl-1,2-benzanthracene (chemistry)
• Benz(a)Anthracenes (chemistry)
• Benzo(a)pyrene (chemistry)
• Carcinogens (chemical synthesis, metabolism)
• Catechols (chemistry)
• Epoxy Compounds (chemistry)
• Molecular Structure
• Oxidation-Reduction
• Polycyclic Aromatic Hydrocarbons (chemical synthesis)
• Quinones (chemical synthesis)
• Stereoisomerism