Synthesis of the o-quinones and other oxidized metabolites of polycyclic aromatic hydrocarbons implicated in carcinogenesis | Health & Environmental Research Online (HERO)

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HERO ID

5121775

Reference Type

Journal Article

Title

Synthesis of the o-quinones and other oxidized metabolites of polycyclic aromatic hydrocarbons implicated in carcinogenesis

Author(s)

Harvey, RG; Dai, Q; Ran, C; Penning, TM

Year

2004

Is Peer Reviewed?

Yes

Journal

Journal of Organic Chemistry
ISSN: 0022-3263
EISSN: 1520-6904

Volume

Issue

Page Numbers

2024-2032

Language

English

PMID

15058949

DOI

10.1021/jo030348n

Web of Science Id

WOS:000220290900034

URL

https://www.scopus.com/inward/record.uri?eid=2-s2.0-1642272391&doi=10.1021%2fjo030348n&partnerID=40&md5=f0da4964987af92fbbeeacea838cf023
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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.