Synthesis and mutagenicity of trans-dihydrodiol metabolites of benzo(b)naphtho(2,1-d)thiophene
- American Health Foundation, Valhalla, NY (USA)
The syntheses of potentially important metabolites of benzo(b)naphtho(2,1-d)thiophene ((2,1)BNT) - trans-1,2-dihydroxy-1,2-dihydrobenzo(b)naphtho(2,1-d)thiophene ((2,1)BNT-1,2-diol) and trans-3,4-dihydroxy-3,4-dihydrobenzo(b)naphtho(2,1-d)thiophene ((2,1)BNT-3,4-diol) - are described. The syntheses involved preparation of the appropriate 1-(3-benzo(b)-thiopheneyl)-2-(methoxyphenyl)ethylenes followed by photocyclization to methoxy-(2,1)BNTs, hydrolysis to hydroxy-(2,1)BNTs, oxidation to (2,1)BNT-diones, and NaBH{sub 4} reduction. The dihydrodiols were tested for mutagenicity in Salmonella typhimurium TA 100 with activation; (2,1)BNT-3,4-diol, which can form a bay region diol epoxide, was a mutagenic as (2,1)BNT whereas (2,1)BNT-1,2-diol was inactive. These results suggest that the metabolic activation of (2,1)BNT proceeds partially via formation of a bay region diol epoxide.
- OSTI ID:
- 6411491
- Journal Information:
- Chemical Research in Toxicology; (USA), Vol. 3:2; ISSN 0893-228X
- Country of Publication:
- United States
- Language:
- English
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Related Subjects
METABOLITES
MUTAGEN SCREENING
SYNTHESIS
CARCINOGENS
METABOLIC ACTIVATION
NMR SPECTRA
POLYCYCLIC AROMATIC HYDROCARBONS
THIOPHENE
AROMATICS
HETEROCYCLIC COMPOUNDS
HYDROCARBONS
ORGANIC COMPOUNDS
ORGANIC SULFUR COMPOUNDS
SCREENING
SPECTRA
560300* - Chemicals Metabolism & Toxicology