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Reactive Metabolites of Carcinogenic Polycyclic Hydrocarbons: Synthesis and Trapping Reaction of 9‐Hydroxybenzo[a]pyrene 4,5‐Oxide
Author(s) -
Bochnitschek Werner,
Seidel Albrecht,
Kunz Horst,
Oesch Franz
Publication year - 1985
Publication title -
angewandte chemie international edition in english
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 0570-0833
DOI - 10.1002/anie.198506991
Subject(s) - pyrene , chemistry , ethanethiol , carcinogen , nucleophile , oxide , dimethyldioxirane , medicinal chemistry , organic chemistry , photochemistry , catalysis
In the Ames test, 9‐hydroxybenzo[a]pyrene is mutagenic. The labile 4,5‐oxide 1 is presumed to be the reactive species. It has been synthesized from 9‐benzo[a]pyrenyl acetate and trapped with ethanethiol. The nucleophilic attack of the thiolate takes place regioselectively at C‐5 of 1. In contrast, benzo[a]pyrene 4,5‐oxide, which lacks a hydroxyl group, is attacked at both C‐4 and C‐5.